bump pointer: internal, .claude/commands (D-434 registration 410: decision, concept doc, plan, backlog, health markers)

Co-Authored-By: Claude Fable 5.2 <noreply@anthropic.com>
Backend: the comment on register-session's 410 sits on its method
2026-11-12 04:35:01 +00:00 · 2026-11-11 17:06:11 +01:00 · 2026-11-11 17:05:40 +01:00 · 2026-11-11 17:05:39 +01:00 · 2026-11-11 15:30:25 +01:00 · 2026-11-11 15:08:01 +01:00
650 changed files with 45082 additions and 6893 deletions
@@ -30,7 +30,7 @@
 - Stage explicit file lists; never `git add -A` or a directory. Pushing is the user's call.
 - New API responses need a typed DTO plus the parity fact. MCP vocabularies are generated from the wire types, never retyped.
 - Every route belongs in the route policy catalog; every new event type goes into the MCP resource catalog.
- Workflow files under `.github/` go through zizmor before they are committed (`zizmor .` from the repository root, findings from severity low on): fix every finding or ignore it in `zizmor.yml` with a reason. The `zizmor` job in `action-pins.yml` runs the same check on every push.
+- Workflow files under `.github/` go through zizmor before they are committed (`zizmor .` from the repository root, findings from severity low on): fix every finding or ignore it in `.github/zizmor.yml` with a reason. The `zizmor` job in `action-pins.yml` runs the same check on every push.
 - The about, terms and privacy pages under `src/Web/autopilot-monitor-web/app/` state facts customers rely on: verify every claim against the code before writing it and update them in the same change as the fact they describe.

 ## Code Quality
@@ -24,6 +24,11 @@ updates:
      dotnet-security:
        applies-to: security-updates
        patterns: ['*']
+    # Application Insights 3 is the OpenTelemetry rewrite (no telemetry processors, another sampling
+    # model) and the Functions worker integration still builds on 2.x: a planned migration, not a bump.
+    ignore:
+      - dependency-name: 'Microsoft.ApplicationInsights.WorkerService'
+        update-types: ['version-update:semver-major']

  - package-ecosystem: npm
    directory: /src/Web/autopilot-monitor-web
@@ -98,6 +103,24 @@ updates:
        applies-to: security-updates
        patterns: ['*']

+  # SWA CLI for the deploy job of deploy-web.yml, which installs it from this lockfile next to
+  # the production deploy token: a version reaches that job only through a reviewed bump here.
+  # deploy-web watches this folder, so a merged bump redeploys and proves the new CLI at once.
+  # Not under .github/: there Dependabot's update PR was refused as an unauthorized change.
+  - package-ecosystem: npm
+    directory: /tools/swa-cli
+    schedule:
+      interval: weekly
+    cooldown:
+      default-days: 7
+    open-pull-requests-limit: 5
+    groups:
+      swa-cli:
+        patterns: ['*']
+      swa-cli-security:
+        applies-to: security-updates
+        patterns: ['*']
+
  # Every action is referenced by commit SHA with the version in a trailing comment;
  # action-pins.yml fails any workflow change that reintroduces a mutable tag. Dependabot
  # is what keeps those pins current: it rewrites the SHA and the comment together, so the
@@ -1,15 +1,18 @@
 name: Workflow gates

-# Three checks over the workflow files and their helper scripts:
+# Four checks over the workflow files and their helper scripts:
 #   * verify-pins -- every third-party action is referenced by a full commit SHA plus a
 #                    version comment (stricter than zizmor's unpinned-uses audit).
 #   * zizmor      -- static analysis of every workflow (permissions, credential
 #                    persistence, template injection, ...). Configuration and the
-#                    reasoned ignores live in zizmor.yml at the repository root; the
-#                    same run is expected locally before a workflow change is committed.
+#                    reasoned ignores live in .github/zizmor.yml, which zizmor finds on
+#                    its own; the same run is expected locally before a workflow change
+#                    is committed.
 #   * hosts       -- no workflow or .github/scripts helper spells out a host; every one
 #                    comes from .github/scripts/Get-Endpoints.ps1, CI's member of the URL
 #                    registry (the C#, web and MCP registries have guard tests of their own).
+#   * packages    -- no workflow or helper fetches a package at a version the repository
+#                    does not fix, in the forms zizmor's adhoc-packages audit does not see.
 #
 # Every third-party action must be referenced by a full commit SHA, never by a tag.
 # Tags are mutable: whoever controls an action repository can repoint v4 at new code,
@@ -37,10 +40,10 @@ name: Workflow gates
 on:
  push:
    branches: [main]
-    paths: ['.github/workflows/**', '.github/scripts/**', '.github/dependabot.yml', 'zizmor.yml']
+    paths: ['.github/workflows/**', '.github/scripts/**', '.github/dependabot.yml', '.github/zizmor.yml']
  pull_request:
    branches: [main]
-    paths: ['.github/workflows/**', '.github/scripts/**', '.github/dependabot.yml', 'zizmor.yml']
+    paths: ['.github/workflows/**', '.github/scripts/**', '.github/dependabot.yml', '.github/zizmor.yml']
  workflow_dispatch:

 permissions:
@@ -105,7 +108,7 @@ jobs:
      # the local install so the gate and the pre-commit run agree on the finding set.
      # Informational findings (template expansion of our own step outputs in pwsh) are
      # visible locally but do not fail the gate.
-      - uses: zizmorcore/zizmor-action@cc914d7f3750a2d13d75c7f184a1060aa0e9d482 # v0.6.4
+      - uses: zizmorcore/zizmor-action@53290badfa369cb0bf7ad16342cb62c2fa47ac7b # v0.8.0
        with:
          version: 1.30.1
          min-severity: low
@@ -123,3 +126,51 @@ jobs:
      - name: No host literal outside .github/scripts/Get-Endpoints.ps1
        shell: pwsh
        run: ./.github/scripts/Assert-HostsFromRegistry.ps1
+
+  packages:
+    name: Packages only at a version the repository fixes
+    runs-on: ubuntu-latest
+    steps:
+      - uses: actions/checkout@3d3c42e5aac5ba805825da76410c181273ba90b1 # v7.0.1
+        with:
+          persist-credentials: false
+
+      # npm packages come from a committed lockfile via npm ci; zizmor's adhoc-packages flags
+      # `npm install <pkg>` (also yarn, pnpm, gem), but not the forms below, which also fetch at
+      # run time:
+      #   * npx / npm exec without --no: in CI they install a missing package without asking.
+      #     The -- is load-bearing: without it npx hands the tool's own flags to npm.
+      #   * a .NET tool without an exact --version, a PowerShell module without -RequiredVersion.
+      # Other package managers (pip, cargo, dlx runners) are covered by neither check.
+      - name: No package fetched at a version the repository does not fix
+        run: |
+          set -uo pipefail
+          failed=0
+          fail() { echo "::error file=$1,line=$2::$3"; failed=1; }
+          while IFS=: read -r file line text; do
+            # YAML, shell and PowerShell comments alike start the line with #.
+            [[ "$text" =~ ^[[:space:]]*# ]] && continue
+
+            if [[ "$text" =~ (^|[^[:alnum:]_./-])(npx|npm[[:space:]]+(exec|x))([[:space:]]|$) ]] &&
+               ! [[ "$text" =~ (npx|npm[[:space:]]+(exec|x))[[:space:]]+--no[[:space:]]+--([[:space:]]|$) ]]; then
+              fail "$file" "$line" "Write 'npx --no -- <tool>' (or 'npm exec --no -- <tool>'): without --no a missing package is fetched from the registry, without -- the tool's flags go to npm."
+            fi
+
+            if [[ "$text" =~ dotnet[[:space:]]+tool[[:space:]]+(install|update) ]] &&
+               ! [[ "$text" =~ --version[[:space:]]+[0-9]+\.[0-9]+\.[0-9]+([^0-9.*]|$) ]]; then
+              fail "$file" "$line" "Give the .NET tool an exact --version X.Y.Z on the same line; a range or a missing version resolves at run time."
+            fi
+
+            if [[ "$text" =~ Install-(Module|PSResource)[[:space:]] ]] &&
+               ! [[ "$text" =~ -RequiredVersion[[:space:]]+[^[:space:]] || "$text" =~ -Version[[:space:]]+[0-9]+\.[0-9]+\.[0-9]+([^0-9.*]|$) ]]; then
+              fail "$file" "$line" "Give the PowerShell module an exact version on the same line, -RequiredVersion for Install-Module, -Version X.Y.Z for Install-PSResource; -MinimumVersion resolves at run time."
+            fi
+          # -H is load-bearing, as in verify-pins: with a single matching file grep omits the name.
+          done < <(grep -nHE 'npx|npm[[:space:]]+(exec|x)([[:space:]]|$)|dotnet[[:space:]]+tool[[:space:]]+(install|update)|Install-(Module|PSResource)' \
+                   .github/workflows/*.yml .github/scripts/*.ps1)
+
+          if [ "$failed" -ne 0 ]; then
+            echo "::error::Packages fetched at a version the repository does not fix -- fix them before this reaches main."
+            exit 1
+          fi
+          echo "Every package the workflows and their helpers fetch has a version the repository fixes."
@@ -65,11 +65,11 @@ jobs:
          persist-credentials: false

      # For all users: the SYSTEM pass below runs Pester as SYSTEM.
-      - name: Install Pester 5+
+      - name: Install Pester
        shell: powershell
        run: |
          Install-PackageProvider -Name NuGet -MinimumVersion 2.8.5.201 -Force -Scope AllUsers | Out-Null
-          Install-Module Pester -Scope AllUsers -Force -SkipPublisherCheck -MinimumVersion 5.5.0
+          Install-Module Pester -Scope AllUsers -Force -SkipPublisherCheck -RequiredVersion 6.2.0

      # Windows PowerShell 5.1 on purpose: that is the runtime IME uses to execute
      # platform scripts, so guard/relax logic is verified without resetting a device.
@@ -247,7 +247,7 @@ jobs:
          Get-ChildItem $outDir | ForEach-Object { Write-Host "$($_.Name): $([math]::Round($_.Length / 1MB, 2)) MB" }

      - name: Upload unsigned build output
-        uses: actions/upload-artifact@043fb46d1a93c77aae656e7c1c64a875d1fc6a0a # v7.0.1
+        uses: actions/upload-artifact@cf430e030ddbb5b0abf93d22962f4752f3646cd9 # v7.0.2
        with:
          name: agent-unsigned
          path: ${{ runner.temp }}/agent-unsigned
@@ -293,7 +293,7 @@ jobs:
        run: ./.github/scripts/Get-Endpoints.ps1 -ExportToGitHubEnv

      - name: Download unsigned build output
-        uses: actions/download-artifact@3e5f45b2cfb9172054b4087a40e8e0b5a5461e7c # v8.0.1
+        uses: actions/download-artifact@9000827ccba6bdab643e8b6fd33ac0654aef8333 # v8.0.2
        with:
          name: agent-unsigned
          path: ${{ runner.temp }}/agent-unsigned
@@ -790,13 +790,13 @@ jobs:
            staging/agent/AutopilotMonitor.SummaryDialog.exe

      - name: Upload build artifact
-        uses: actions/upload-artifact@043fb46d1a93c77aae656e7c1c64a875d1fc6a0a # v7.0.1
+        uses: actions/upload-artifact@cf430e030ddbb5b0abf93d22962f4752f3646cd9 # v7.0.2
        with:
          name: AutopilotMonitor-Agent-v${{ needs.reserve.outputs.version }}
          path: ${{ steps.artifact.outputs.versioned_zip_release }}

      - name: Upload version metadata
-        uses: actions/upload-artifact@043fb46d1a93c77aae656e7c1c64a875d1fc6a0a # v7.0.1
+        uses: actions/upload-artifact@cf430e030ddbb5b0abf93d22962f4752f3646cd9 # v7.0.2
        with:
          name: version-metadata
          path: ${{ env.MANIFEST_NAME }}
@@ -127,7 +127,7 @@ jobs:
          Write-Host "$env:RUNNER_SCRIPT : Valid, timestamped, signer $($sig.SignerCertificate.Subject.Split(',')[0])"

      - name: Upload signed loader
-        uses: actions/upload-artifact@043fb46d1a93c77aae656e7c1c64a875d1fc6a0a # v7.0.1
+        uses: actions/upload-artifact@cf430e030ddbb5b0abf93d22962f4752f3646cd9 # v7.0.2
        with:
          name: bootstrap-loader-signed
          path: ${{ env.RUNNER_SCRIPT }}
@@ -148,7 +148,7 @@ jobs:
          persist-credentials: false

      - name: Download signed loader
-        uses: actions/download-artifact@3e5f45b2cfb9172054b4087a40e8e0b5a5461e7c # v8.0.1
+        uses: actions/download-artifact@9000827ccba6bdab643e8b6fd33ac0654aef8333 # v8.0.2
        with:
          name: bootstrap-loader-signed
          path: ${{ runner.temp }}/loader
@@ -187,7 +187,7 @@ jobs:
          Write-Host "Built $env:STABLE_MSI ($([math]::Round((Get-Item $env:STABLE_MSI).Length / 1KB)) KB)"

      - name: Upload unsigned MSI
-        uses: actions/upload-artifact@043fb46d1a93c77aae656e7c1c64a875d1fc6a0a # v7.0.1
+        uses: actions/upload-artifact@cf430e030ddbb5b0abf93d22962f4752f3646cd9 # v7.0.2
        with:
          name: bootstrap-msi-unsigned
          path: ${{ env.STABLE_MSI }}
@@ -215,7 +215,7 @@ jobs:
          persist-credentials: false

      - name: Download unsigned MSI
-        uses: actions/download-artifact@3e5f45b2cfb9172054b4087a40e8e0b5a5461e7c # v8.0.1
+        uses: actions/download-artifact@9000827ccba6bdab643e8b6fd33ac0654aef8333 # v8.0.2
        with:
          name: bootstrap-msi-unsigned
          path: ${{ runner.temp }}/msi
@@ -310,7 +310,7 @@ jobs:
          "version=$version" >> $env:GITHUB_OUTPUT

      - name: Download unsigned MSI
-        uses: actions/download-artifact@3e5f45b2cfb9172054b4087a40e8e0b5a5461e7c # v8.0.1
+        uses: actions/download-artifact@9000827ccba6bdab643e8b6fd33ac0654aef8333 # v8.0.2
        with:
          name: bootstrap-msi-unsigned
          path: ${{ runner.temp }}/msi
@@ -442,7 +442,7 @@ jobs:
          subject-path: ${{ env.STABLE_MSI }}

      - name: Upload build artifact
-        uses: actions/upload-artifact@043fb46d1a93c77aae656e7c1c64a875d1fc6a0a # v7.0.1
+        uses: actions/upload-artifact@cf430e030ddbb5b0abf93d22962f4752f3646cd9 # v7.0.2
        with:
          name: AutopilotMonitor-Bootstrap-v${{ steps.version.outputs.version }}
          path: ${{ env.STABLE_MSI }}
@@ -24,7 +24,7 @@ on:
      - 'infra/**'
      - '.claude/**'
      - '.gitmodules'
-      - 'zizmor.yml'
+      - '.github/zizmor.yml'
      - '**/*.md'
      - 'LICENSE'
      - '.github/ISSUE_TEMPLATE/**'
@@ -56,7 +56,7 @@ on:
      - 'infra/**'
      - '.claude/**'
      - '.gitmodules'
-      - 'zizmor.yml'
+      - '.github/zizmor.yml'
      - '**/*.md'
      - 'LICENSE'
      - '.github/ISSUE_TEMPLATE/**'
@@ -134,7 +134,7 @@ jobs:
        with:
          persist-credentials: false

-      - uses: actions/setup-node@820762786026740c76f36085b0efc47a31fe5020 # v7.0.0
+      - uses: actions/setup-node@949feb2413d6458794dcd2491c4babbbce0c15c1 # v7.1.0
        with:
          node-version: '22'
          cache: npm
@@ -145,10 +145,10 @@ jobs:
      # next-env.d.ts + .next type stubs are gitignored (Next-managed since
      # v16); typegen generates them so tsc sees the same types as a build.
      - name: Generate Next.js types
-        run: npx next typegen
+        run: npx --no -- next typegen

      - name: Typecheck
-        run: npx tsc --noEmit
+        run: npx --no -- tsc --noEmit

      # Errors fail outright, and so does ANY warning: the codebase is
      # warning-clean and must stay that way — fix new findings, never
@@ -176,7 +176,7 @@ jobs:
        with:
          persist-credentials: false

-      - uses: actions/setup-node@820762786026740c76f36085b0efc47a31fe5020 # v7.0.0
+      - uses: actions/setup-node@949feb2413d6458794dcd2491c4babbbce0c15c1 # v7.1.0
        with:
          node-version: '22'
          cache: npm
@@ -187,7 +187,7 @@ jobs:
      # tsconfig.json covers sources, tests and scripts; the build emits via
      # tsconfig.build.json.
      - name: Typecheck
-        run: npx tsc --noEmit
+        run: npx --no -- tsc --noEmit

      # Same rule as the web job: any warning fails — fix new findings, never
      # raise the cap.
@@ -222,7 +222,7 @@ jobs:
        with:
          persist-credentials: false

-      - uses: actions/setup-node@820762786026740c76f36085b0efc47a31fe5020 # v7.0.0
+      - uses: actions/setup-node@949feb2413d6458794dcd2491c4babbbce0c15c1 # v7.1.0
        with:
          node-version: '22'

@@ -245,7 +245,7 @@ jobs:
        with:
          persist-credentials: false

-      - uses: actions/setup-node@820762786026740c76f36085b0efc47a31fe5020 # v7.0.0
+      - uses: actions/setup-node@949feb2413d6458794dcd2491c4babbbce0c15c1 # v7.1.0
        with:
          node-version: '22'

@@ -276,7 +276,7 @@ jobs:
        with:
          persist-credentials: false

-      - uses: actions/setup-node@820762786026740c76f36085b0efc47a31fe5020 # v7.0.0
+      - uses: actions/setup-node@949feb2413d6458794dcd2491c4babbbce0c15c1 # v7.1.0
        with:
          node-version: '22'
          cache: npm
@@ -17,7 +17,7 @@ on:
      - 'infra/**'
      - '.claude/**'
      - '.gitmodules'
-      - 'zizmor.yml'
+      - '.github/zizmor.yml'
      - '**/*.md'
      - 'LICENSE'
      - '.github/ISSUE_TEMPLATE/**'
@@ -48,7 +48,7 @@ on:
      - 'infra/**'
      - '.claude/**'
      - '.gitmodules'
-      - 'zizmor.yml'
+      - '.github/zizmor.yml'
      - '**/*.md'
      - 'LICENSE'
      - '.github/ISSUE_TEMPLATE/**'
@@ -112,7 +112,7 @@ jobs:
          dotnet-version: '10.0.x'

      - name: Initialize CodeQL
-        uses: github/codeql-action/init@2892aa5e19bbd11bc0cff5427e3b750a04d9e3c2 # v4.38.2
+        uses: github/codeql-action/init@9b3254085494b55a0f7c4c2b3d2d52cc712ce370 # v4.39.1
        with:
          languages: ${{ matrix.language }}
          build-mode: ${{ matrix.build-mode }}
@@ -123,6 +123,6 @@ jobs:
        run: dotnet build AutopilotMonitor.sln --configuration Release

      - name: Analyze
-        uses: github/codeql-action/analyze@2892aa5e19bbd11bc0cff5427e3b750a04d9e3c2 # v4.38.2
+        uses: github/codeql-action/analyze@9b3254085494b55a0f7c4c2b3d2d52cc712ce370 # v4.39.1
        with:
          category: /language:${{ matrix.language }}
@@ -32,7 +32,7 @@ jobs:
        with:
          persist-credentials: false

-      - uses: actions/setup-node@820762786026740c76f36085b0efc47a31fe5020 # v7.0.0
+      - uses: actions/setup-node@949feb2413d6458794dcd2491c4babbbce0c15c1 # v7.1.0
        with:
          node-version: '22'

@@ -66,7 +66,7 @@ jobs:
      # `git push` needs.
      - uses: actions/checkout@3d3c42e5aac5ba805825da76410c181273ba90b1 # v7.0.1

-      - uses: actions/setup-node@820762786026740c76f36085b0efc47a31fe5020 # v7.0.0
+      - uses: actions/setup-node@949feb2413d6458794dcd2491c4babbbce0c15c1 # v7.1.0
        with:
          node-version: '22'

@@ -99,7 +99,7 @@ jobs:
        run: tar -czf "$RUNNER_TEMP/backend-publish.tgz" -C publish .

      - name: Upload publish output
-        uses: actions/upload-artifact@043fb46d1a93c77aae656e7c1c64a875d1fc6a0a # v7.0.1
+        uses: actions/upload-artifact@cf430e030ddbb5b0abf93d22962f4752f3646cd9 # v7.0.2
        with:
          name: backend-publish
          path: ${{ runner.temp }}/backend-publish.tgz
@@ -128,7 +128,7 @@ jobs:
        run: ./.github/scripts/Get-Endpoints.ps1 -ExportToGitHubEnv

      - name: Download publish output
-        uses: actions/download-artifact@3e5f45b2cfb9172054b4087a40e8e0b5a5461e7c # v8.0.1
+        uses: actions/download-artifact@9000827ccba6bdab643e8b6fd33ac0654aef8333 # v8.0.2
        with:
          name: backend-publish
          path: ${{ runner.temp }}/backend-artifact
@@ -1,14 +1,14 @@
 name: Deploy Web (Static Web App)

-# Build here, upload with the pinned SWA CLI. No third-party action sees the deploy token
-# (the CLI is Microsoft-published npm code at an exact version), the build runs on the same
-# path ci.yml tests (setup-node 22 + npm ci + next build) instead of Oryx guessing inside the
-# action's container, and the exported site is attested like the agent ZIP and the MSI.
+# Build here, upload with the SWA CLI from its own lockfile (tools/swa-cli). No
+# third-party action sees the deploy token, the build runs on the same path ci.yml tests
+# (setup-node 22 + npm ci + next build) instead of Oryx guessing inside the action's container,
+# and the exported site is attested like the agent ZIP and the MSI.
 #
-# Three jobs, each holding only what it needs: build runs all third-party code without any
-# credential, deploy holds the SWA token alone, record attests, verifies and writes the
-# manifest. A failed record job is re-run on its own; it writes only once the live site
-# serves this commit.
+# Three jobs, each holding only what it needs: build runs the third-party build code without
+# any credential, deploy holds the SWA token alone and runs nothing but the locked CLI, record
+# attests, verifies and writes the manifest. A failed record job is re-run on its own; it
+# writes only once the live site serves this commit.
 #
 # PR preview environments were dropped with the action: their per-PR URLs are never
 # registered as redirect URIs, so nobody could log in on them anyway.
@@ -19,6 +19,7 @@ on:
      - main
    paths:
      - 'src/Web/autopilot-monitor-web/**'
+      - 'tools/swa-cli/**'
      - '.github/workflows/deploy-web.yml'
  workflow_dispatch:

@@ -32,9 +33,6 @@ permissions:
 # repository variable.
 env:
  WEB_DIR: src/Web/autopilot-monitor-web
-  # Exact version: `npx --package` resolves from the registry at run time, so the pin is the
-  # only thing that keeps the deploy step's code fixed. Bump deliberately.
-  SWA_CLI_VERSION: 2.0.10

 jobs:
  # Build zone: no login, no id-token. The one secret here is the Application Insights
@@ -74,7 +72,7 @@ jobs:
        id: docs
        run: echo "sha=$(git -C whats-new-docs rev-parse HEAD)" >> "$GITHUB_OUTPUT"

-      - uses: actions/setup-node@820762786026740c76f36085b0efc47a31fe5020 # v7.0.0
+      - uses: actions/setup-node@949feb2413d6458794dcd2491c4babbbce0c15c1 # v7.1.0
        with:
          node-version: '22'
          cache: npm
@@ -149,14 +147,15 @@ jobs:
          sha256sum "$archive"

      - name: Upload build artifact
-        uses: actions/upload-artifact@043fb46d1a93c77aae656e7c1c64a875d1fc6a0a # v7.0.1
+        uses: actions/upload-artifact@cf430e030ddbb5b0abf93d22962f4752f3646cd9 # v7.0.2
        with:
          name: portal-${{ github.sha }}
          path: ${{ steps.package.outputs.archive }}
          if-no-files-found: error

-  # Holds the SWA deployment token and nothing else -- deliberately no id-token: the SWA CLI
-  # is third-party npm code whose dependencies resolve at run time.
+  # Holds the SWA deployment token and nothing else -- deliberately no id-token. The token alone
+  # can replace the portal, so the SWA CLI, the one third-party code here, comes from a committed
+  # lockfile: a version published after the last reviewed bump never runs next to it.
  deploy:
    name: Deploy to Static Web App
    needs: build
@@ -164,13 +163,21 @@ jobs:
    environment: production

    steps:
-      # For staticwebapp.config.json only.
+      # For staticwebapp.config.json and the CLI's lockfile.
      - uses: actions/checkout@3d3c42e5aac5ba805825da76410c181273ba90b1 # v7.0.1
        with:
          persist-credentials: false

+      # npm ci, never npx or npm install: the lockfile pins every transitive package by hash.
+      # No lifecycle scripts: keytar, the only package with one, serves the keychain, which
+      # --no-use-keychain keeps unloaded. Before the artifact arrives, so nothing from the
+      # build zone can touch the install.
+      - name: Install the SWA CLI from its lockfile
+        working-directory: tools/swa-cli
+        run: npm ci --ignore-scripts
+
      - name: Download build artifact
-        uses: actions/download-artifact@3e5f45b2cfb9172054b4087a40e8e0b5a5461e7c # v8.0.1
+        uses: actions/download-artifact@9000827ccba6bdab643e8b6fd33ac0654aef8333 # v8.0.2
        with:
          name: portal-${{ github.sha }}
          path: ${{ runner.temp }}/portal
@@ -186,7 +193,7 @@ jobs:
        env:
          SWA_CLI_DEPLOYMENT_TOKEN: ${{ secrets.AZURE_SWA_DEPLOY_TOKEN }}
        run: |
-          npx --yes --package "@azure/static-web-apps-cli@${SWA_CLI_VERSION}" swa deploy \
+          tools/swa-cli/node_modules/.bin/swa deploy \
            --app-location "$WEB_DIR" \
            --output-location out \
            --swa-config-location "$WEB_DIR" \
@@ -215,7 +222,7 @@ jobs:
        run: ./.github/scripts/Get-Endpoints.ps1 -ExportToGitHubEnv

      - name: Download build artifact
-        uses: actions/download-artifact@3e5f45b2cfb9172054b4087a40e8e0b5a5461e7c # v8.0.1
+        uses: actions/download-artifact@9000827ccba6bdab643e8b6fd33ac0654aef8333 # v8.0.2
        with:
          name: portal-${{ github.sha }}
          path: ${{ runner.temp }}/portal
@@ -150,7 +150,7 @@ jobs:
      # when someone wants to look at the file.
      - name: Upload signed scripts
        if: always()
-        uses: actions/upload-artifact@043fb46d1a93c77aae656e7c1c64a875d1fc6a0a # v7.0.1
+        uses: actions/upload-artifact@cf430e030ddbb5b0abf93d22962f4752f3646cd9 # v7.0.2
        with:
          name: signed-scripts
          path: ${{ runner.temp }}/signed-scripts
@@ -1,9 +1,15 @@
+# The three submodules are private. "update = none" makes recursive clones skip them (the
+# public, Dependabot's NuGet updater); a clone with access sets
+# submodule.<name>.update = checkout once, or runs git submodule update --init --checkout.
 [submodule ".claude/commands"]
 	path = .claude/commands
 	url = https://github.com/okieselbach/Autopilot-Monitor-dotclaude.git
+	update = none
 [submodule "docs"]
 	path = internal
 	url = https://github.com/okieselbach/Autopilot-Monitor-internal.git
+	update = none
 [submodule "infra"]
 	path = infra
 	url = https://github.com/okieselbach/Autopilot-Monitor-infra.git
+	update = none
@@ -2,10 +2,10 @@
  "$schema": "../schema/analyze-rule.schema.json",
  "ruleId": "ANALYZE-ID-002",
  "title": "Unexpected Local Admin Accounts Detected",
-  "description": "Detects when the LocalAdminAnalyzer flags unexpected local user accounts or profile directories on the device. This is a known Autopilot bypass technique where admin accounts are created before or during enrollment to gain persistent local admin access.",
+  "description": "Detects when the LocalAdminAnalyzer flags unexpected local user accounts on the device, including accounts allowed only as standard users that hold local admin rights. This is a known Autopilot bypass technique where admin accounts are created before or during enrollment to gain persistent local admin access.",
  "severity": "high",
  "category": "identity",
-  "version": "1.4.0",
+  "version": "1.5.0",
  "author": "Autopilot Monitor",
  "enabled": true,
  "evaluateOn": [
@@ -65,6 +65,18 @@
      "filterOperator": "equals",
      "filterValue": "unexpected_local_admins_detected",
      "required": false
+    },
+    {
+      "signal": "role_violations",
+      "source": "event_data",
+      "eventType": "local_admin_analysis",
+      "dataField": "checks.role_violations",
+      "operator": "not_equals",
+      "value": "",
+      "filterField": "finding",
+      "filterOperator": "equals",
+      "filterValue": "unexpected_local_admins_detected",
+      "required": false
    }
  ],
  "confidenceFactors": [
@@ -80,7 +92,7 @@
    }
  ],
  "confidenceThreshold": 50,
-  "explanation": "The agent detected unexpected local user accounts or profile directories on this device that are not in the built-in or tenant-configured allowed list.\n\nThis is a security-relevant finding. Creating local admin accounts before or during Autopilot enrollment is a known bypass technique (e.g. via BypassNRO or Shift+F10 during OOBE) that grants persistent local administrator access.\n\nClick the event link below to jump to the local_admin_analysis event and check: unexpected_accounts (local user accounts not on the allowed list — disabled accounts included, a dormant account can be re-enabled later), unexpected_admin_members (unexpected accounts that are members of the local Administrators group — the actual backdoor), account_details (per account: disabled state and Administrators membership), unexpected_profiles (C:\\Users profile directories not on the allowed list), logged_in_local_accounts (local accounts that were signed in when the shutdown scan ran — a signed-in local account is never exempted, only Entra/domain users are), bypass_nro (whether the BypassNRO registry flag was set), and confidence_score (the agent's confidence in the finding, 0-100).\n\nIf these accounts are expected for your environment (e.g. a service account or helpdesk account), add them to the allowed list in Tenant Settings.",
+  "explanation": "The agent detected unexpected local user accounts on this device: accounts the built-in or tenant-configured allowed list does not allow, or accounts it allows only as standard users that are members of the local Administrators group.\n\nThis is a security-relevant finding. Creating local admin accounts before or during Autopilot enrollment is a known bypass technique (e.g. via BypassNRO or Shift+F10 during OOBE) that grants persistent local administrator access.\n\nClick the event link below to jump to the local_admin_analysis event and check: unexpected_accounts (local user accounts not allowed by the list — disabled accounts included, a dormant account can be re-enabled later), unexpected_admin_members (unexpected accounts that are members of the local Administrators group — the actual backdoor), role_violations (accounts allowed only as standard users that are members of Administrators — Windows never puts Guest, kioskUser0 or WsiAccount there), account_details (per account: disabled state, Administrators membership and RID — 500 is the built-in Administrator), unexpected_profiles (C:\\Users profile directories not on the allowed list), logged_in_local_accounts (local accounts that were signed in when the shutdown scan ran — a signed-in local account is never exempted, only Entra/domain users are), bypass_nro (whether the BypassNRO registry flag was set), and confidence_score (the agent's confidence in the finding, 0-100).\n\nIf these accounts are expected for your environment (e.g. a service account or helpdesk account), add them to the allowed list under Settings → Agent Analyzers. Choose Standard user only for an account that must never be a local administrator.",
  "remediation": [
    {
      "title": "Review the unexpected accounts",
@@ -94,7 +106,8 @@
      "title": "Add expected accounts to the allowed list (false positive)",
      "steps": [
        "Go to Settings → Agent Analyzers section",
-        "Under 'Allowed Admin Accounts', add the account names that are expected in your environment",
+        "Under 'Allowed Local Accounts', add the account names that are expected in your environment",
+        "Choose 'Standard user only' for an account that must not be a local administrator — it is still reported if it ever joins the Administrators group",
        "Save the settings — future enrollments will no longer flag these accounts"
      ]
    },
@@ -104,6 +117,7 @@
        "Check if the BypassNRO registry flag was set (indicates OOBE was bypassed)",
        "Review the enrollment timeline for Shift+F10 or other OOBE escape indicators",
        "Check 'unexpected_admin_members' and 'account_details' — an unexpected account with Administrators membership is a backdoor even while it is disabled (it can be re-enabled by a scheduled task after enrollment)",
+        "Check 'role_violations' — a built-in Windows account or an account you allowed as standard user that sits in Administrators was put there on purpose",
        "Consider re-imaging the device if unauthorized admin access is confirmed"
      ]
    }
@@ -126,6 +140,11 @@
        "label": "In Administrators",
        "value": "{{unexpected_admin_members.value}}",
        "format": "code"
+      },
+      {
+        "label": "Allowed only as standard user",
+        "value": "{{role_violations.value}}",
+        "format": "code"
      }
    ]
  },
@@ -4103,10 +4103,10 @@
    {
      "ruleId": "ANALYZE-ID-002",
      "title": "Unexpected Local Admin Accounts Detected",
-      "description": "Detects when the LocalAdminAnalyzer flags unexpected local user accounts or profile directories on the device. This is a known Autopilot bypass technique where admin accounts are created before or during enrollment to gain persistent local admin access.",
+      "description": "Detects when the LocalAdminAnalyzer flags unexpected local user accounts on the device, including accounts allowed only as standard users that hold local admin rights. This is a known Autopilot bypass technique where admin accounts are created before or during enrollment to gain persistent local admin access.",
      "severity": "high",
      "category": "identity",
-      "version": "1.4.0",
+      "version": "1.5.0",
      "author": "Autopilot Monitor",
      "enabled": true,
      "evaluateOn": [
@@ -4166,6 +4166,18 @@
          "filterOperator": "equals",
          "filterValue": "unexpected_local_admins_detected",
          "required": false
+        },
+        {
+          "signal": "role_violations",
+          "source": "event_data",
+          "eventType": "local_admin_analysis",
+          "dataField": "checks.role_violations",
+          "operator": "not_equals",
+          "value": "",
+          "filterField": "finding",
+          "filterOperator": "equals",
+          "filterValue": "unexpected_local_admins_detected",
+          "required": false
        }
      ],
      "confidenceFactors": [
@@ -4181,7 +4193,7 @@
        }
      ],
      "confidenceThreshold": 50,
-      "explanation": "The agent detected unexpected local user accounts or profile directories on this device that are not in the built-in or tenant-configured allowed list.\n\nThis is a security-relevant finding. Creating local admin accounts before or during Autopilot enrollment is a known bypass technique (e.g. via BypassNRO or Shift+F10 during OOBE) that grants persistent local administrator access.\n\nClick the event link below to jump to the local_admin_analysis event and check: unexpected_accounts (local user accounts not on the allowed list — disabled accounts included, a dormant account can be re-enabled later), unexpected_admin_members (unexpected accounts that are members of the local Administrators group — the actual backdoor), account_details (per account: disabled state and Administrators membership), unexpected_profiles (C:\\Users profile directories not on the allowed list), logged_in_local_accounts (local accounts that were signed in when the shutdown scan ran — a signed-in local account is never exempted, only Entra/domain users are), bypass_nro (whether the BypassNRO registry flag was set), and confidence_score (the agent's confidence in the finding, 0-100).\n\nIf these accounts are expected for your environment (e.g. a service account or helpdesk account), add them to the allowed list in Tenant Settings.",
+      "explanation": "The agent detected unexpected local user accounts on this device: accounts the built-in or tenant-configured allowed list does not allow, or accounts it allows only as standard users that are members of the local Administrators group.\n\nThis is a security-relevant finding. Creating local admin accounts before or during Autopilot enrollment is a known bypass technique (e.g. via BypassNRO or Shift+F10 during OOBE) that grants persistent local administrator access.\n\nClick the event link below to jump to the local_admin_analysis event and check: unexpected_accounts (local user accounts not allowed by the list — disabled accounts included, a dormant account can be re-enabled later), unexpected_admin_members (unexpected accounts that are members of the local Administrators group — the actual backdoor), role_violations (accounts allowed only as standard users that are members of Administrators — Windows never puts Guest, kioskUser0 or WsiAccount there), account_details (per account: disabled state, Administrators membership and RID — 500 is the built-in Administrator), unexpected_profiles (C:\\Users profile directories not on the allowed list), logged_in_local_accounts (local accounts that were signed in when the shutdown scan ran — a signed-in local account is never exempted, only Entra/domain users are), bypass_nro (whether the BypassNRO registry flag was set), and confidence_score (the agent's confidence in the finding, 0-100).\n\nIf these accounts are expected for your environment (e.g. a service account or helpdesk account), add them to the allowed list under Settings → Agent Analyzers. Choose Standard user only for an account that must never be a local administrator.",
      "remediation": [
        {
          "title": "Review the unexpected accounts",
@@ -4195,7 +4207,8 @@
          "title": "Add expected accounts to the allowed list (false positive)",
          "steps": [
            "Go to Settings → Agent Analyzers section",
-            "Under 'Allowed Admin Accounts', add the account names that are expected in your environment",
+            "Under 'Allowed Local Accounts', add the account names that are expected in your environment",
+            "Choose 'Standard user only' for an account that must not be a local administrator — it is still reported if it ever joins the Administrators group",
            "Save the settings — future enrollments will no longer flag these accounts"
          ]
        },
@@ -4205,6 +4218,7 @@
            "Check if the BypassNRO registry flag was set (indicates OOBE was bypassed)",
            "Review the enrollment timeline for Shift+F10 or other OOBE escape indicators",
            "Check 'unexpected_admin_members' and 'account_details' — an unexpected account with Administrators membership is a backdoor even while it is disabled (it can be re-enabled by a scheduled task after enrollment)",
+            "Check 'role_violations' — a built-in Windows account or an account you allowed as standard user that sits in Administrators was put there on purpose",
            "Consider re-imaging the device if unauthorized admin access is confirmed"
          ]
        }
@@ -4227,6 +4241,11 @@
            "label": "In Administrators",
            "value": "{{unexpected_admin_members.value}}",
            "format": "code"
+          },
+          {
+            "label": "Allowed only as standard user",
+            "value": "{{role_violations.value}}",
+            "format": "code"
          }
        ]
      },
@@ -89,12 +89,14 @@
          "type": "array",
          "description": "Conditions evaluated against the event stream. All required conditions must match for the rule to fire.",
          "items": { "$ref": "#/$defs/ruleCondition" },
-          "minItems": 1
+          "minItems": 1,
+          "maxItems": 20
        },
        "preconditions": {
          "type": "array",
          "description": "Optional device-fact gates evaluated BEFORE conditions. ALL preconditions must pass; if any fails the rule is silently skipped — no result, no UI card. Useful for filtering out hardware/OS profiles where the rule does not apply (e.g. virtual machines).",
          "items": { "$ref": "#/$defs/rulePrecondition" },
+          "maxItems": 10,
          "default": []
        },
        "baseConfidence": {
@@ -18,9 +18,9 @@
  </ItemGroup>

  <ItemGroup>
-    <PackageReference Include="Microsoft.NET.Test.Sdk" Version="17.11.1" />
-    <PackageReference Include="xunit" Version="2.9.2" />
-    <PackageReference Include="xunit.runner.visualstudio" Version="2.8.2">
+    <PackageReference Include="Microsoft.NET.Test.Sdk" Version="18.11.0" />
+    <PackageReference Include="xunit" Version="2.9.3" />
+    <PackageReference Include="xunit.runner.visualstudio" Version="4.0.1">
      <IncludeAssets>runtime; build; native; contentfiles; analyzers; buildtransitive</IncludeAssets>
      <PrivateAssets>all</PrivateAssets>
    </PackageReference>
@@ -44,7 +44,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Harness
            IReadOnlyCollection<string>? whiteGloveSealingPatternIds = null,
            TimeSpan? drainInterval = null,
            TimeSpan? terminalDrainTimeout = null,
-            TimeSpan? agentMaxLifetime = null) =>
+            TimeSpan? agentMaxLifetime = null,
+            TimeSpan? collectorHostStopTimeout = null) =>
            new EnrollmentOrchestrator(
                sessionId: "S1",
                tenantId: "T1",
@@ -58,7 +59,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Harness
                whiteGloveSealingPatternIds: whiteGloveSealingPatternIds,
                drainInterval: drainInterval ?? TimeSpan.FromDays(1),
                terminalDrainTimeout: terminalDrainTimeout ?? TimeSpan.FromSeconds(2),
-                agentMaxLifetime: agentMaxLifetime);
+                agentMaxLifetime: agentMaxLifetime,
+                collectorHostStopTimeout: collectorHostStopTimeout);

        public void Dispose() => Tmp.Dispose();
    }
@@ -0,0 +1,45 @@
+#nullable enable
+using System.Collections.Generic;
+using System.IO;
+using System.Linq;
+using AutopilotMonitor.Agent.V2.Core.Tests.Harness;
+using AutopilotMonitor.Shared.Models;
+using Newtonsoft.Json.Linq;
+using Xunit;
+
+namespace AutopilotMonitor.Agent.V2.Core.Tests.Monitoring.Analyzers
+{
+    /// <summary>
+    /// <c>tests/fixtures/local-admin-allow-list/cases.json</c> run against the netstandard2.0 build of
+    /// <see cref="LocalAdminAllowList"/> — the one the agent ships. The backend runs the same file against
+    /// its net10.0 build, the portal against <c>allowedAccounts.ts</c>.
+    /// </summary>
+    public sealed class LocalAdminAllowListFixtureTests
+    {
+        private static IEnumerable<JToken> ParseCases()
+        {
+            var path = Path.Combine(RepoPaths.Fixtures("local-admin-allow-list"), "cases.json");
+            return JObject.Parse(File.ReadAllText(path))["parse"]!;
+        }
+
+        public static IEnumerable<object[]> ParseEntries() => ParseCases().Select(c => new object[] { c.Value<string>("entry")! });
+
+        [Theory]
+        [MemberData(nameof(ParseEntries))]
+        public void Agent_parses_the_entry_as_the_shared_case_says(string entry)
+        {
+            var c = ParseCases().First(x => x.Value<string>("entry") == entry);
+
+            var parsed = LocalAdminAllowList.TryParseEntry(entry, out var pattern, out var role);
+
+            if (c.Value<bool?>("ignored") == true)
+            {
+                Assert.False(parsed);
+                return;
+            }
+            Assert.True(parsed);
+            Assert.Equal(c.Value<string>("pattern"), pattern);
+            Assert.Equal(c.Value<string>("role") == "user" ? LocalAccountRole.StandardUser : LocalAccountRole.Any, role);
+        }
+    }
+}
@@ -18,10 +18,9 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Monitoring.Analyzers
        private const string Machine = "DESKTOP-TEST01";
        private const string MachineSidPrefix = "S-1-5-21-111-222-333-";

-        private static readonly List<string> Allowed = new List<string>
-        {
-            "Administrator", "Guest", "DefaultAccount", "WDAGUtilityAccount", "defaultuser0", "defaultuser1", "adm-*"
-        };
+        // The real built-in catalog plus one tenant glob.
+        private static readonly List<LocalAdminAnalyzer.AllowedEntry> Allowed =
+            LocalAdminAnalyzer.BuildAllowedEntries(new[] { "adm-*" }, new List<string>());

        private static LocalAdminAnalyzer.LocalAccountInfo Account(string name, bool disabled, int rid) =>
            new LocalAdminAnalyzer.LocalAccountInfo { Name = name, Disabled = disabled, Sid = MachineSidPrefix + rid };
@@ -126,7 +125,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Monitoring.Analyzers
        [Fact]
        public void Local_admin_member_missing_from_the_wmi_inventory_is_still_flagged()
        {
-            // WMI failed or did not list the account — the SAM group membership alone is enough.
+            // WMI failed or did not list the account — the SAM group membership alone is enough,
+            // and the account counts as unexpected too, like any unknown administrator (score 80).
            var members = new List<LocalGroupMember>
            {
                LocalMember("Administrator", 500),
@@ -136,8 +136,9 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Monitoring.Analyzers
            var result = LocalAdminAnalyzer.EvaluateAccounts(
                new List<LocalAdminAnalyzer.LocalAccountInfo>(), members, true, Machine, Allowed);

-            Assert.Empty(result.Unexpected);
+            Assert.Equal(new[] { "backdoor" }, result.Unexpected);
            Assert.Equal(new[] { "backdoor" }, result.UnexpectedAdminMembers);
+            Assert.Empty(result.RoleViolations);
        }

        [Fact]
@@ -191,26 +192,24 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Monitoring.Analyzers
        }

        [Fact]
-        public void Well_known_rid_does_not_cover_ordinary_accounts_or_foreign_sids()
+        public void Machine_account_rid_is_read_only_from_local_machine_sids()
        {
-            Assert.True(LocalAdminAnalyzer.IsWellKnownBuiltInRid(MachineSidPrefix + "500"));
-            Assert.True(LocalAdminAnalyzer.IsWellKnownBuiltInRid(MachineSidPrefix + "501"));
-            Assert.True(LocalAdminAnalyzer.IsWellKnownBuiltInRid(MachineSidPrefix + "503"));
-            Assert.True(LocalAdminAnalyzer.IsWellKnownBuiltInRid(MachineSidPrefix + "504"));
-            Assert.False(LocalAdminAnalyzer.IsWellKnownBuiltInRid(MachineSidPrefix + "502"));
-            Assert.False(LocalAdminAnalyzer.IsWellKnownBuiltInRid(MachineSidPrefix + "1500"));
-            Assert.False(LocalAdminAnalyzer.IsWellKnownBuiltInRid(MachineSidPrefix + "1001"));
-            Assert.False(LocalAdminAnalyzer.IsWellKnownBuiltInRid("S-1-12-1-1-2-3-500"));
-            Assert.False(LocalAdminAnalyzer.IsWellKnownBuiltInRid("S-1-5-32-544"));
-            Assert.False(LocalAdminAnalyzer.IsWellKnownBuiltInRid(MachineSidPrefix));
-            Assert.False(LocalAdminAnalyzer.IsWellKnownBuiltInRid(null));
-            Assert.False(LocalAdminAnalyzer.IsWellKnownBuiltInRid(""));
+            Assert.Equal(500, LocalAdminAnalyzer.MachineAccountRid(MachineSidPrefix + "500"));
+            Assert.Equal(501, LocalAdminAnalyzer.MachineAccountRid(MachineSidPrefix + "501"));
+            Assert.Equal(1001, LocalAdminAnalyzer.MachineAccountRid(MachineSidPrefix + "1001"));
+            Assert.Null(LocalAdminAnalyzer.MachineAccountRid("S-1-12-1-1-2-3-500"));
+            Assert.Null(LocalAdminAnalyzer.MachineAccountRid("S-1-5-32-544"));
+            Assert.Null(LocalAdminAnalyzer.MachineAccountRid(MachineSidPrefix));
+            Assert.Null(LocalAdminAnalyzer.MachineAccountRid(MachineSidPrefix + "x1"));
+            Assert.Null(LocalAdminAnalyzer.MachineAccountRid(null!));
+            Assert.Null(LocalAdminAnalyzer.MachineAccountRid(""));
        }

        [Fact]
-        public void Account_named_like_a_builtin_but_with_an_ordinary_rid_is_still_matched_by_name_only()
+        public void Localized_builtin_name_on_an_ordinary_rid_is_not_allowed()
        {
-            // Name-based allowance is unchanged: the RID match only ADDS coverage.
+            // Only the RID makes a built-in: an ordinary account merely named like a localized
+            // built-in is no entry at all.
            var accounts = new List<LocalAdminAnalyzer.LocalAccountInfo>
            {
                Account("Gast", disabled: false, rid: 1001)
@@ -0,0 +1,349 @@
+#nullable enable
+using System.Collections.Generic;
+using System.Linq;
+using AutopilotMonitor.Agent.V2.Core.Monitoring.Interop;
+using AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Analyzers;
+using AutopilotMonitor.Shared.Models;
+using Xunit;
+
+namespace AutopilotMonitor.Agent.V2.Core.Tests.Monitoring.Analyzers
+{
+    /// <summary>
+    /// Roles on the allowed list: <c>name|user</c> and the standard-user built-ins (Guest,
+    /// DefaultAccount, WDAGUtilityAccount by RID; kioskUser0, WsiAccount and other accounts carrying a
+    /// built-in name by name) allow an account only while it is not an Administrators member. A
+    /// restriction always wins; the four built-in accounts are decided by RID alone; profile folders
+    /// have no role; a login allows a profile folder, never an account. All names are synthetic.
+    /// </summary>
+    public sealed class LocalAdminAnalyzerRoleTests
+    {
+        private const string Machine = "DESKTOP-TEST01";
+        private const string MachineSidPrefix = "S-1-5-21-111-222-333-";
+
+        private static List<LocalAdminAnalyzer.AllowedEntry> Entries(params string[] tenantEntries)
+            => LocalAdminAnalyzer.BuildAllowedEntries(tenantEntries, new List<string>());
+
+        private static LocalAdminAnalyzer.LocalAccountInfo Account(string name, int rid, bool disabled = false) =>
+            new LocalAdminAnalyzer.LocalAccountInfo { Name = name, Disabled = disabled, Sid = MachineSidPrefix + rid };
+
+        private static LocalGroupMember Member(string name, int rid) =>
+            new LocalGroupMember { DomainAndName = Machine + "\\" + name, Sid = MachineSidPrefix + rid, SidUsage = 1 };
+
+        private static LocalAdminAnalyzer.LocalAccountCheckResult Evaluate(
+            IList<LocalAdminAnalyzer.LocalAccountInfo> accounts, IList<LocalGroupMember> admins, List<LocalAdminAnalyzer.AllowedEntry> entries,
+            bool enumerated = true)
+            => LocalAdminAnalyzer.EvaluateAccounts(accounts, admins, enumerated, Machine, entries);
+
+        // -------------------------------------------------------------- WsiAccount (the field case)
+
+        [Fact]
+        public void WsiAccount_as_standard_user_with_its_profile_folder_scores_zero()
+        {
+            // The field case: web sign-in enabled the account for the sign-in, it holds no admin
+            // membership and has C:\Users\WsiAccount — before roles existed this scored 80 (Error).
+            var accounts = new[]
+            {
+                Account("Administrator", 500, disabled: true),
+                Account("DefaultAccount", 503, disabled: true),
+                Account("defaultuser0", 1000, disabled: true),
+                Account("Gast", 501, disabled: true),
+                Account("WDAGUtilityAccount", 504, disabled: true),
+                Account("WsiAccount", 1001, disabled: true),
+                Account("ADM-0A1B2C3D", 1002),
+            };
+            var admins = new List<LocalGroupMember>
+            {
+                Member("Administrator", 500),
+                new LocalGroupMember { DomainAndName = "S-1-12-1-11-22-33-44", Sid = "S-1-12-1-11-22-33-44", SidUsage = 8 },
+                Member("ADM-0A1B2C3D", 1002),
+            };
+
+            var result = Evaluate(accounts, admins, Entries("ADM-*"));
+            var score = LocalAdminAnalyzer.ComputeConfidenceScore(
+                bypassNro: false, result.Unexpected, result.UnexpectedAdminMembers, new List<string> { "jane.doe" });
+
+            Assert.Empty(result.Unexpected);
+            Assert.Empty(result.UnexpectedAdminMembers);
+            Assert.Empty(result.RoleViolations);
+            Assert.Equal(0, score);
+        }
+
+        [Fact]
+        public void WsiAccount_in_administrators_is_a_role_violation_even_while_disabled()
+        {
+            var result = Evaluate(
+                new[] { Account("WsiAccount", 1001, disabled: true) },
+                new List<LocalGroupMember> { Member("WsiAccount", 1001) },
+                Entries());
+
+            Assert.Equal(new[] { "WsiAccount" }, result.Unexpected);
+            Assert.Equal(new[] { "WsiAccount" }, result.UnexpectedAdminMembers);
+            Assert.Equal(new[] { "WsiAccount" }, result.RoleViolations);
+            Assert.Equal(80, LocalAdminAnalyzer.ComputeConfidenceScore(
+                false, result.Unexpected, result.UnexpectedAdminMembers, new List<string>()));
+        }
+
+        [Theory]
+        [InlineData("WsiAccount")]
+        [InlineData("wsiaccount")]
+        [InlineData("Wsi*")]
+        [InlineData("*")]
+        public void Tenant_entries_cannot_lift_a_builtin_restriction(string tenantEntry)
+        {
+            var result = Evaluate(
+                new[] { Account("WsiAccount", 1001) },
+                new List<LocalGroupMember> { Member("WsiAccount", 1001) },
+                Entries(tenantEntry));
+
+            Assert.Equal(new[] { "WsiAccount" }, result.RoleViolations);
+        }
+
+        [Fact]
+        public void KioskUser0_in_administrators_is_a_role_violation()
+        {
+            var result = Evaluate(
+                new[] { Account("kioskUser0", 1003) },
+                new List<LocalGroupMember> { Member("kioskUser0", 1003) },
+                Entries());
+
+            Assert.Equal(new[] { "kioskUser0" }, result.RoleViolations);
+        }
+
+        // -------------------------------------------------------------- built-ins by RID
+
+        [Theory]
+        [InlineData("Guest", 501)]
+        [InlineData("Gast", 501)]
+        [InlineData("Invité", 501)]
+        [InlineData("DefaultAccount", 503)]
+        [InlineData("WDAGUtilityAccount", 504)]
+        public void Builtin_accounts_that_are_never_administrators_are_flagged_as_one(string name, int rid)
+        {
+            // A tenant entry naming the localized account (or even "*") cannot lift it either.
+            var result = Evaluate(
+                new[] { Account(name, rid, disabled: true) },
+                new List<LocalGroupMember> { Member(name, rid) },
+                Entries(name, "*"));
+
+            Assert.Equal(new[] { name }, result.Unexpected);
+            Assert.Equal(new[] { name }, result.UnexpectedAdminMembers);
+            Assert.Equal(new[] { name }, result.RoleViolations);
+        }
+
+        [Theory]
+        [InlineData("Administrator")]
+        [InlineData("Administrateur")]
+        [InlineData("Renamed_Admin")]
+        public void The_builtin_administrator_is_allowed_by_rid_under_any_name(string name)
+        {
+            // "Admin*|user" must not turn the real Administrator into a finding: name entries never
+            // decide the RID accounts — and the built-in name entry "Administrator|user" neither.
+            var result = Evaluate(
+                new[] { Account(name, 500) },
+                new List<LocalGroupMember> { Member(name, 500) },
+                Entries("Admin*|user", "Renamed*|user"));
+
+            Assert.Empty(result.Unexpected);
+            Assert.Empty(result.RoleViolations);
+            Assert.True(result.BuiltInAdministratorEnabled);
+        }
+
+        [Fact]
+        public void An_ordinary_account_named_administrator_is_allowed_only_as_a_decoy()
+        {
+            // French device: the RID-500 account is "Administrateur", so "Administrator" is free.
+            var accounts = new[]
+            {
+                Account("Administrateur", 500, disabled: true),
+                Account("Administrator", 1004),
+            };
+
+            var decoy = Evaluate(accounts, new List<LocalGroupMember> { Member("Administrateur", 500) }, Entries());
+            Assert.Empty(decoy.Unexpected);
+
+            var impostor = Evaluate(accounts,
+                new List<LocalGroupMember> { Member("Administrateur", 500), Member("Administrator", 1004) }, Entries());
+            Assert.Equal(new[] { "Administrator" }, impostor.RoleViolations);
+            Assert.Equal(new[] { "Administrator" }, impostor.UnexpectedAdminMembers);
+        }
+
+        [Fact]
+        public void The_oobe_account_may_be_an_administrator()
+        {
+            var result = Evaluate(
+                new[] { Account("defaultuser0", 1000) },
+                new List<LocalGroupMember> { Member("defaultuser0", 1000) },
+                Entries());
+
+            Assert.Empty(result.Unexpected);
+        }
+
+        [Fact]
+        public void A_missing_sid_lets_the_english_builtin_name_stand_in_for_the_rid()
+        {
+            var accounts = new List<LocalAdminAnalyzer.LocalAccountInfo>
+            {
+                new LocalAdminAnalyzer.LocalAccountInfo { Name = "Administrator", Disabled = false, Sid = null! },
+                new LocalAdminAnalyzer.LocalAccountInfo { Name = "Guest", Disabled = false, Sid = null! },
+            };
+            var admins = new List<LocalGroupMember>
+            {
+                new LocalGroupMember { DomainAndName = Machine + "\\Administrator", Sid = null!, SidUsage = 1 },
+                new LocalGroupMember { DomainAndName = Machine + "\\Guest", Sid = null!, SidUsage = 1 },
+            };
+
+            var result = Evaluate(accounts, admins, Entries());
+
+            Assert.Equal(new[] { "Guest" }, result.RoleViolations);
+            Assert.DoesNotContain("Administrator", result.Unexpected);
+        }
+
+        // -------------------------------------------------------------- tenant roles
+
+        [Fact]
+        public void A_standard_user_entry_allows_the_account_until_it_is_an_administrator()
+        {
+            var accounts = new[] { Account("frontdesk", 1005) };
+
+            Assert.Empty(Evaluate(accounts, new List<LocalGroupMember>(), Entries("frontdesk|user")).Unexpected);
+
+            var admin = Evaluate(accounts, new List<LocalGroupMember> { Member("frontdesk", 1005) }, Entries("frontdesk|user"));
+            Assert.Equal(new[] { "frontdesk" }, admin.RoleViolations);
+        }
+
+        [Fact]
+        public void A_standard_user_glob_restricts_each_matching_account()
+        {
+            var accounts = new[] { Account("svc-print", 1006), Account("svc-scan", 1007) };
+
+            var result = Evaluate(accounts, new List<LocalGroupMember> { Member("svc-scan", 1007) }, Entries("svc-*|user"));
+
+            Assert.Equal(new[] { "svc-scan" }, result.Unexpected);
+            Assert.Equal(new[] { "svc-scan" }, result.RoleViolations);
+        }
+
+        [Fact]
+        public void A_restriction_wins_over_a_broader_entry_that_allows_more()
+        {
+            var accounts = new[] { Account("adm-kiosk", 1008), Account("adm-4711", 1009) };
+            var admins = new List<LocalGroupMember> { Member("adm-kiosk", 1008), Member("adm-4711", 1009) };
+
+            var result = Evaluate(accounts, admins, Entries("adm-*", "adm-kiosk|user"));
+
+            Assert.Equal(new[] { "adm-kiosk" }, result.RoleViolations);
+            Assert.DoesNotContain("adm-4711", result.Unexpected);
+        }
+
+        [Fact]
+        public void Membership_unknown_lets_a_standard_user_entry_act_like_a_plain_one()
+        {
+            // Enumeration failed: nobody is known to be an administrator, so nothing is a violation.
+            var result = Evaluate(new[] { Account("WsiAccount", 1001) }, new List<LocalGroupMember>(), Entries(), enumerated: false);
+
+            Assert.Empty(result.Unexpected);
+            Assert.False(result.AdministratorsGroupEnumerated);
+        }
+
+        // -------------------------------------------------------------- folders are no accounts
+
+        [Fact]
+        public void An_account_named_like_a_profile_folder_is_unexpected_while_the_folder_is_allowed()
+        {
+            var entries = Entries();
+
+            var result = Evaluate(new[] { Account("Public", 1010) }, new List<LocalGroupMember> { Member("Public", 1010) }, entries);
+
+            Assert.Equal(new[] { "Public" }, result.Unexpected);
+            Assert.Equal(new[] { "Public" }, result.UnexpectedAdminMembers);
+            Assert.Empty(result.RoleViolations);
+            Assert.Equal(LocalAdminAnalyzer.AccountDecision.Unlisted,
+                LocalAdminAnalyzer.Decide("Public", MachineSidPrefix + "1010", isAdmin: false, entries));
+            Assert.Contains(entries, e => e.Pattern == "Public" && e.ProfileFolderOnly);
+        }
+
+        // -------------------------------------------------------------- accounts WMI did not return
+
+        [Fact]
+        public void Administrators_members_missing_from_wmi_are_judged_as_administrators()
+        {
+            var members = new List<LocalGroupMember>
+            {
+                Member("Administrator", 500),
+                Member("WsiAccount", 1001),
+                Member("Gast", 501),
+                Member("adm-4711", 1009),
+            };
+
+            var result = Evaluate(new List<LocalAdminAnalyzer.LocalAccountInfo>(), members, Entries("adm-*"));
+
+            Assert.Equal(new[] { "WsiAccount", "Gast" }, result.RoleViolations);
+            Assert.Equal(new[] { "WsiAccount", "Gast" }, result.Unexpected);
+            Assert.Equal(new[] { "WsiAccount", "Gast" }, result.UnexpectedAdminMembers);
+        }
+
+        [Fact]
+        public void A_member_wmi_already_returned_is_not_judged_twice()
+        {
+            var result = Evaluate(
+                new[] { Account("backdoor", 1011) },
+                new List<LocalGroupMember> { Member("backdoor", 1011) },
+                Entries());
+
+            Assert.Equal(new[] { "backdoor" }, result.Unexpected);
+            Assert.Equal(new[] { "backdoor" }, result.UnexpectedAdminMembers);
+        }
+
+        [Fact]
+        public void A_login_never_allows_an_account_not_even_when_wmi_failed()
+        {
+            // WMI failed: the split cannot recognise "backdoor" as local and allows it dynamically.
+            // The dynamic entry is folder-only, so the signed-in backdoor administrator is still found.
+            var split = LocalAdminAnalyzer.SplitLoggedInUsers(new[] { "backdoor" }, null!);
+            var entries = Entries();
+            entries.AddRange(split.Allowed.Select(u => new LocalAdminAnalyzer.AllowedEntry(u, LocalAccountRole.Any, profileFolderOnly: true)));
+
+            var result = Evaluate(new List<LocalAdminAnalyzer.LocalAccountInfo>(), new List<LocalGroupMember> { Member("backdoor", 1011) }, entries);
+
+            Assert.Equal(new[] { "backdoor" }, result.UnexpectedAdminMembers);
+            Assert.Equal(new[] { "backdoor" }, result.Unexpected);
+        }
+
+        // -------------------------------------------------------------- the entry list
+
+        [Fact]
+        public void Entries_carry_the_builtins_and_skip_invalid_tenant_entries()
+        {
+            var ignored = new List<string>();
+            var entries = LocalAdminAnalyzer.BuildAllowedEntries(
+                new[] { "kiosk|user", "x|admin", "|user", "legacy*", "CONTOSO\\admin", "   ", "Guest|user" }, ignored);
+
+            Assert.Equal(new[] { "x|admin", "|user" }, ignored);
+            var accounts = entries.Where(e => !e.ProfileFolderOnly).Select(e => e.Display).ToList();
+            Assert.Contains("WsiAccount|user", accounts);
+            Assert.Contains("kioskUser0|user", accounts);
+            Assert.Contains("defaultuser0", accounts);
+            Assert.Contains("kiosk|user", accounts);
+            Assert.Contains("legacy*", accounts);
+            Assert.Contains("CONTOSO\\admin", accounts);
+            Assert.Single(accounts, a => a == "Guest|user");
+            Assert.DoesNotContain("Public", accounts);
+            Assert.Contains(entries, e => e.Pattern == "All Users" && e.ProfileFolderOnly);
+        }
+
+        // -------------------------------------------------------------- scoring
+
+        [Fact]
+        public void Score_follows_the_signals()
+        {
+            var none = new List<string>();
+            var backdoor = new List<string> { "backdoor" };
+
+            Assert.Equal(0, LocalAdminAnalyzer.ComputeConfidenceScore(false, none, none, backdoor));
+            Assert.Equal(20, LocalAdminAnalyzer.ComputeConfidenceScore(true, none, none, none));
+            Assert.Equal(40, LocalAdminAnalyzer.ComputeConfidenceScore(false, backdoor, none, none));
+            Assert.Equal(80, LocalAdminAnalyzer.ComputeConfidenceScore(false, backdoor, backdoor, none));
+            Assert.Equal(80, LocalAdminAnalyzer.ComputeConfidenceScore(false, backdoor, none, new List<string> { "BACKDOOR" }));
+            Assert.Equal(100, LocalAdminAnalyzer.ComputeConfidenceScore(true, backdoor, backdoor, backdoor));
+        }
+    }
+}
@@ -0,0 +1,277 @@
+using System.Collections.Generic;
+using System.IO;
+using System.Linq;
+using System.Threading.Tasks;
+using AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.Ime;
+using AutopilotMonitor.Shared.Models;
+using Xunit;
+
+namespace AutopilotMonitor.Agent.V2.Core.Tests.Monitoring.Ime
+{
+    /// <summary>
+    /// IME rolls a log with File.Move at 3 MB. The tracker used to take the archive for a new file and
+    /// read it from 0: every app line played again, finished apps fell back to Installing and the
+    /// subgraph line of an older app marked the running app as skipped (session 190fed00).
+    /// </summary>
+    public sealed partial class ImeLogTrackerOverwriteRewindTests
+    {
+        private const string FirstStamp = "20260910-193000";
+        private const string SecondStamp = "20260910-193500";
+
+        private static string Folder(Harness h) => Path.GetDirectoryName(h.LogPath)!;
+
+        private static string ArchivePath(Harness h, string stamp = FirstStamp)
+            => Path.Combine(Folder(h), $"{Path.GetFileNameWithoutExtension(h.LogName)}-{stamp}.log");
+
+        private static string Roll(Harness h, string stamp = FirstStamp)
+        {
+            var archive = ArchivePath(h, stamp);
+            File.Move(h.LogPath, archive);
+            return archive;
+        }
+
+        private static List<ImeLogPattern> AppPatterns() => new List<ImeLogPattern>
+        {
+            new ImeLogPattern
+            {
+                PatternId = "T-POLICIES", Category = "always", Enabled = true,
+                Pattern = @"^policies discovered = (?<policies>\[.*\])", Action = "policiesDiscovered",
+                Parameters = new Dictionary<string, string>(),
+            },
+            new ImeLogPattern
+            {
+                PatternId = "T-SUBGRAPH", Category = "always", Enabled = true,
+                Pattern = @"^subgraph (?<id>[\w-]+)", Action = "cancelStuckAndSetCurrent",
+                Parameters = new Dictionary<string, string>(),
+            },
+            new ImeLogPattern
+            {
+                PatternId = "T-INSTALLING", Category = "always", Enabled = true,
+                Pattern = @"^installing (?<id>[\w-]+)", Action = "updateStateInstalling",
+                Parameters = new Dictionary<string, string>(),
+            },
+            new ImeLogPattern
+            {
+                PatternId = "T-INSTALLED", Category = "always", Enabled = true,
+                Pattern = @"^installed (?<id>[\w-]+)", Action = "updateStateInstalled",
+                Parameters = new Dictionary<string, string>(),
+            },
+        };
+
+        private const string AppPoliciesLine = @"policies discovered = [{""Id"":""app-1"",""Name"":""App One""},{""Id"":""app-2"",""Name"":""App Two""}]";
+
+        private static string OneFinishedOneRunning() =>
+            Entry(AppPoliciesLine) + Entry("subgraph app-1") + Entry("installing app-1") + Entry("installed app-1")
+            + Entry("subgraph app-2") + Entry("installing app-2");
+
+        [Theory]
+        [InlineData("AppWorkload.log")]
+        [InlineData("AppActionProcessor.log")]
+        [InlineData("HealthScripts.log")]
+        [InlineData("AgentExecutor.log")]
+        [InlineData("IntuneManagementExtension.log")]
+        public async Task Rolled_over_log_is_not_read_again(string logName)
+        {
+            using var h = new Harness(logName, MarkerPatterns());
+            h.Append(Entry("marker 1") + Entry("marker 2") + Entry("marker 3"));
+            await h.Pass();
+
+            Roll(h);
+            h.Append(Entry("marker 4"));
+            h.Now = h.Now.AddMilliseconds(100);
+            await h.Pass();
+            Assert.Equal(new[] { 1, 2, 3, 4 }, h.Matched());
+
+            h.Tracker.RequestOverwriteCheckForTest();
+            h.Now = h.Now.AddSeconds(2);
+            await h.Pass();
+            Assert.Equal(new[] { 1, 2, 3, 4 }, h.Matched());
+            Assert.Equal(0, h.Health.OverwriteRewinds);
+        }
+
+        [Fact]
+        public async Task Bytes_written_after_the_last_read_come_from_the_archive_once_and_first()
+        {
+            using var h = new Harness("AppWorkload.log", MarkerPatterns());
+            h.Append(Entry("marker 1") + Entry("marker 2"));
+            await h.Pass();
+
+            h.Append(Entry("marker 3"));
+            Roll(h);
+            h.Append(Entry("marker 4"));
+            h.Now = h.Now.AddMilliseconds(100);
+            await h.Pass();
+
+            Assert.Equal(new[] { 1, 2, 3, 4 }, h.Matched());
+        }
+
+        [Fact]
+        public async Task Line_held_back_at_the_end_of_the_file_is_finished_from_the_archive()
+        {
+            using var h = new Harness("AppWorkload.log", MarkerPatterns());
+            var second = Entry("marker 2");
+            h.Append(Entry("marker 1") + second.Substring(0, 10));
+            await h.Pass();
+            Assert.Equal(new[] { 1 }, h.Matched());
+
+            h.Append(second.Substring(10));
+            Roll(h);
+            h.Append(Entry("marker 3"));
+            h.Now = h.Now.AddMilliseconds(100);
+            await h.Pass();
+
+            Assert.Equal(new[] { 1, 2, 3 }, h.Matched());
+        }
+
+        [Fact]
+        public async Task Rollover_leaves_finished_and_running_apps_alone()
+        {
+            using var h = new Harness("AppWorkload.log", AppPatterns());
+            var transitions = new List<string>();
+            h.Tracker.OnAppStateChanged = (pkg, from, to) => transitions.Add($"{pkg.Id}:{from}->{to}");
+            h.Append(OneFinishedOneRunning());
+            await h.Pass();
+            var before = transitions.ToList();
+
+            Roll(h);
+            h.Append(Entry("marker unrelated"));
+            h.Now = h.Now.AddMilliseconds(100);
+            await h.Pass();
+
+            Assert.Equal(before, transitions);
+            var states = h.Tracker.GetAllKnownPackageStates().ToDictionary(p => p.Id, p => p.InstallationState);
+            Assert.Equal(AppInstallationState.Installed, states["app-1"]);
+            Assert.Equal(AppInstallationState.Installing, states["app-2"]);
+        }
+
+        [Fact]
+        public async Task Without_a_readable_identity_the_archive_is_read_again_as_before()
+        {
+            // The fallback, and the proof that the tests above catch the replay: this is what they saw before the fix.
+            using var h = new Harness("AppWorkload.log", AppPatterns());
+            h.Tracker.FileIdentityProvider = _ => null!;
+            var transitions = new List<string>();
+            h.Tracker.OnAppStateChanged = (pkg, from, to) => transitions.Add($"{pkg.Id}:{from}->{to}");
+            h.Append(OneFinishedOneRunning());
+            await h.Pass();
+
+            Roll(h);
+            h.Append(Entry("marker unrelated"));
+            h.Now = h.Now.AddMilliseconds(100);
+            await h.Pass();
+
+            Assert.Contains("app-2:Installing->Skipped", transitions);
+            Assert.Contains("app-1:Installed->Installing", transitions);
+        }
+
+        [Fact]
+        public async Task Live_file_that_sorts_before_its_archive_hands_over_its_bookmark()
+        {
+            // LogMaxHistory <= 1: the archive is _X.log, which sorts behind X.log. The pass reaches the
+            // shrunken live file first, and the next rollover replaces the archive under the same name.
+            using var h = new Harness("IntuneManagementExtension.log", MarkerPatterns());
+            var archive = Path.Combine(Folder(h), "_IntuneManagementExtension.log");
+            h.Append(Entry("marker 1") + Entry("marker 2") + Entry("marker 3") + Entry("marker 4"));
+            await h.Pass();
+
+            File.Move(h.LogPath, archive);
+            h.Append(Entry("marker 5"));
+            h.Now = h.Now.AddMilliseconds(100);
+            await h.Pass();
+            Assert.Equal(new[] { 1, 2, 3, 4, 5 }, h.Matched());
+
+            h.Append(Entry("marker 6"));
+            File.Delete(archive);
+            File.Move(h.LogPath, archive);
+            h.Append(Entry("marker 8"));
+            h.Now = h.Now.AddMilliseconds(100);
+            await h.Pass();
+            h.Now = h.Now.AddMilliseconds(100);
+            await h.Pass();
+            Assert.Equal(new[] { 1, 2, 3, 4, 5, 6, 8 }, h.Matched());
+        }
+
+        [Fact]
+        public async Task Rollover_during_a_restart_with_a_longer_new_file_loses_and_repeats_nothing()
+        {
+            using var h = new Harness("AppWorkload.log", MarkerPatterns());
+            h.Append(Entry("marker 1") + Entry("marker 2"));
+            await h.Pass();
+
+            h.Restart();
+            h.Append(Entry("marker 3"));
+            Roll(h);
+            h.Append(Entry("marker 4") + Entry("marker 5") + Entry("marker 6") + Entry("marker 7"));
+            await h.Pass();
+
+            Assert.Equal(new[] { 1, 2, 3, 4, 5, 6, 7 }, h.Matched());
+        }
+
+        [Fact]
+        public async Task Two_rollovers_during_a_restart_with_the_bookmarked_file_deleted_lose_nothing()
+        {
+            using var h = new Harness("AppWorkload.log", MarkerPatterns());
+            h.Append(Entry("marker 1") + Entry("marker 2"));
+            await h.Pass();
+
+            h.Restart();
+            var first = Roll(h, FirstStamp);
+            h.Append(Entry("marker 3"));
+            Roll(h, SecondStamp);
+            h.Append(Entry("marker 4") + Entry("marker 5") + Entry("marker 6"));
+            File.Delete(first);
+            await h.Pass();
+
+            Assert.Equal(new[] { 1, 2, 3, 4, 5, 6 }, h.Matched());
+        }
+
+        [Fact]
+        public async Task Archives_found_at_the_first_start_are_read_from_the_beginning_in_order()
+        {
+            using var h = new Harness("AppWorkload.log", MarkerPatterns());
+            File.WriteAllText(ArchivePath(h, FirstStamp), Entry("marker 1") + Entry("marker 2"));
+            File.WriteAllText(ArchivePath(h, SecondStamp), Entry("marker 3"));
+            h.Append(Entry("marker 4"));
+
+            await h.Pass();
+
+            Assert.Equal(new[] { 1, 2, 3, 4 }, h.Matched());
+        }
+
+        [Fact]
+        public async Task Platform_script_in_flight_keeps_its_end_block_across_a_rollover()
+        {
+            // Reading the archive again used to restore the marker of the run in flight by accident.
+            using var h = new Harness("AgentExecutor.log", ScriptPatterns());
+            h.Append(Entry("ExecutorLog AgentExecutor gets invoked") + Entry(PlatformStartLine) + Entry("[Executor] created powershell with process id 12708"));
+            await h.Pass();
+
+            Roll(h);
+            h.Append(Entry("Powershell exit code is 0") + Entry("write output done. output = Hello from E, error = ") + Entry("Agent executor completed."));
+            h.Now = h.Now.AddMilliseconds(100);
+            await h.Pass();
+
+            h.Tracker.ProcessLogMessageForTest(ResultLine);
+            var script = Assert.Single(h.Completed);
+            Assert.Equal(PlatformId, script.PolicyId);
+            Assert.Equal(0, script.ExitCode);
+            Assert.Equal("Hello from E", script.Stdout);
+        }
+
+        [Fact]
+        public void Identity_of_a_real_file_survives_a_rename_and_differs_from_the_next_file()
+        {
+            using var h = new Harness("AppWorkload.log", MarkerPatterns());
+            h.Append(Entry("marker 1"));
+            var before = ImeLogFileIdentity.TryRead(h.LogPath);
+            Assert.NotNull(before);
+
+            var archive = Roll(h);
+            h.Append(Entry("marker 2"));
+
+            Assert.Equal(before, ImeLogFileIdentity.TryRead(archive));
+            Assert.NotEqual(before, ImeLogFileIdentity.TryRead(h.LogPath));
+            Assert.Null(ImeLogFileIdentity.TryRead(archive + ".missing"));
+        }
+    }
+}
@@ -3,6 +3,7 @@ using System.Collections.Generic;
 using System.Diagnostics;
 using System.Linq;
 using System.Threading;
+using System.Threading.Tasks;
 using AutopilotMonitor.Agent.V2.Core.Logging;
 using AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.Ime;
 using AutopilotMonitor.Agent.V2.Core.Orchestration;
@@ -13,6 +14,8 @@ using AutopilotMonitor.DecisionCore.Signals;
 using Xunit;
 using SharedEventTypes = AutopilotMonitor.Shared.Constants.EventTypes;

+#pragma warning disable xUnit1031 // one test waits on a task on purpose: a blocked call is the failure it looks for
+
 namespace AutopilotMonitor.Agent.V2.Core.Tests.Monitoring.Ime
 {
    /// <summary>
@@ -137,6 +140,12 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Monitoring.Ime
            public void Dispose()
            {
                Watcher.Dispose();
+                ReleaseProcessesAndFiles();
+            }
+
+            /// <summary>Teardown that leaves the watcher alone — for a test that found its Dispose blocked.</summary>
+            public void ReleaseProcessesAndFiles()
+            {
                foreach (var p in Running)
                {
                    try { if (!p.HasExited) p.Kill(); } catch { }
@@ -210,6 +219,48 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Monitoring.Ime
            Assert.Equal(new object[] { first.Id, second.Id }, pids);
        }

+        [Fact]
+        public void Dispose_returns_while_the_exit_of_the_attached_process_is_being_delivered()
+        {
+            var f = new Fixture();
+            var child = f.Spawn(trusted: true);
+
+            // The watcher gets a Process object that already carries a handler. .NET runs that one
+            // first and holds its own lock on the Process object for as long as it delivers Exited.
+            var delivering = new ManualResetEventSlim(false);
+            var release = new ManualResetEventSlim(false);
+            f.Watcher.ProcessSource = () =>
+            {
+                var handle = Process.GetProcessById(child.Id);
+                handle.EnableRaisingEvents = true;
+                handle.Exited += (_, __) => { delivering.Set(); release.Wait(TimeSpan.FromSeconds(10)); };
+                return new[] { handle };
+            };
+            f.Watcher.TryAttachNow();
+            Assert.Equal(child.Id, f.Watcher.AttachedProcessId);
+
+            Task dispose;
+            try
+            {
+                child.Kill();
+                Assert.True(delivering.Wait(TimeSpan.FromSeconds(10)), "the exit was not delivered");
+
+                dispose = Task.Run(() => f.Watcher.Dispose());
+                Thread.Sleep(300); // let Dispose reach the Process object
+            }
+            finally
+            {
+                release.Set();
+            }
+
+            var returned = dispose.Wait(TimeSpan.FromSeconds(10));
+            // A blocked Dispose holds the watcher's lock for good; disposing the watcher again would
+            // hang the test run instead of failing this test.
+            f.ReleaseProcessesAndFiles();
+            Assert.True(returned,
+                "Dispose and the exit delivery blocked each other: the Process is disposed under the watcher's lock");
+        }
+
        [Fact]
        public void With_spoof_and_service_both_running_the_service_wins_regardless_of_order()
        {
@@ -0,0 +1,187 @@
+using System;
+using System.Collections.Generic;
+using AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.Ime;
+using Xunit;
+
+namespace AutopilotMonitor.Agent.V2.Core.Tests.Monitoring.Ime
+{
+    /// <summary>
+    /// A bookmark belongs to a file, not to a name: IME rolls a log by renaming it, so the identity
+    /// (volume plus file index) tells what happened to the bytes behind the bookmark.
+    /// </summary>
+    public sealed class LogFilePositionTrackerTests
+    {
+        private const string Live = @"C:\Logs\AppWorkload.log";
+        private const string Archive = @"C:\Logs\AppWorkload-20260910-193000.log";
+        private const string Underscore = @"C:\Logs\_AppWorkload.log";
+
+        private static readonly DateTime Checked = new DateTime(2026, 9, 10, 19, 30, 0, DateTimeKind.Utc);
+
+        private static Dictionary<string, string> Ids(params (string Path, string Id)[] entries)
+        {
+            var ids = new Dictionary<string, string>(StringComparer.OrdinalIgnoreCase);
+            foreach (var entry in entries) ids[entry.Path] = entry.Id;
+            return ids;
+        }
+
+        private static LogFilePositionTracker TrackerWithBookmark(string path, string id, long position)
+        {
+            var tracker = new LogFilePositionTracker();
+            tracker.Reconcile(Ids((path, id)));
+            tracker.MarkChecked(path, Checked);
+            tracker.SetPosition(path, position);
+            return tracker;
+        }
+
+        [Fact]
+        public void Renamed_file_keeps_its_bookmark_and_the_old_path_starts_over()
+        {
+            var tracker = TrackerWithBookmark(Live, "A", 3000);
+
+            var moves = tracker.Reconcile(Ids((Archive, "A"), (Live, "B")));
+
+            var move = Assert.Single(moves);
+            Assert.Equal(Live, move.From);
+            Assert.Equal(Archive, move.To);
+            Assert.Equal(3000, move.Position);
+            Assert.Equal(3000, tracker.GetPosition(Archive));
+            Assert.Equal("A", tracker.GetFileId(Archive));
+            Assert.Equal(0, tracker.GetPosition(Live));
+            Assert.Equal("B", tracker.GetFileId(Live));
+        }
+
+        [Fact]
+        public void Both_paths_keep_the_freshness_reference()
+        {
+            var tracker = TrackerWithBookmark(Live, "A", 3000);
+
+            tracker.Reconcile(Ids((Archive, "A"), (Live, "B")));
+
+            Assert.True(tracker.HasSeen(Archive));
+            Assert.Equal(Checked, tracker.GetLastCheckedUtc(Archive));
+            Assert.True(tracker.HasSeen(Live));
+            Assert.Equal(Checked, tracker.GetLastCheckedUtc(Live));
+        }
+
+        [Fact]
+        public void Renamed_file_whose_old_path_is_not_recreated_yet_keeps_its_bookmark()
+        {
+            var tracker = TrackerWithBookmark(Live, "A", 3000);
+
+            var moves = tracker.Reconcile(Ids((Archive, "A")));
+
+            Assert.Single(moves);
+            Assert.Equal(3000, tracker.GetPosition(Archive));
+            Assert.Equal(0, tracker.GetPosition(Live));
+            Assert.False(tracker.HasIdentity(Live));
+        }
+
+        [Fact]
+        public void Second_name_for_the_same_file_moves_nothing()
+        {
+            var tracker = TrackerWithBookmark(Live, "A", 3000);
+
+            var moves = tracker.Reconcile(Ids((Live, "A"), (Archive, "A")));
+
+            Assert.Empty(moves);
+            Assert.Equal(3000, tracker.GetPosition(Live));
+            Assert.False(tracker.HasSeen(Archive));
+        }
+
+        [Fact]
+        public void Unknown_file_stays_unseen_so_its_first_pass_is_not_taken_for_fresh_lines()
+        {
+            var tracker = TrackerWithBookmark(Live, "A", 3000);
+
+            var moves = tracker.Reconcile(Ids((Live, "A"), (Archive, "X")));
+
+            Assert.Empty(moves);
+            Assert.True(tracker.HasIdentity(Archive));
+            Assert.False(tracker.HasSeen(Archive));
+            Assert.Equal(0, tracker.GetPosition(Archive));
+        }
+
+        [Fact]
+        public void Path_holding_another_file_with_no_one_to_take_over_starts_at_zero()
+        {
+            var tracker = TrackerWithBookmark(Live, "A", 3000);
+
+            var moves = tracker.Reconcile(Ids((Live, "B")));
+
+            Assert.Empty(moves);
+            // GetSafePosition alone would keep 3000 here when the new file is longer: lost lines.
+            Assert.Equal(0, tracker.GetSafePosition(Live, 5000));
+            Assert.Equal("B", tracker.GetFileId(Live));
+        }
+
+        [Fact]
+        public void Unreadable_identity_changes_nothing()
+        {
+            var tracker = TrackerWithBookmark(Live, "A", 3000);
+
+            var moves = tracker.Reconcile(Ids((Live, null!), (Archive, null!)));
+
+            Assert.Empty(moves);
+            Assert.Equal(3000, tracker.GetPosition(Live));
+            Assert.Equal("A", tracker.GetFileId(Live));
+            Assert.True(tracker.HasIdentity(Archive));
+            Assert.Null(tracker.GetFileId(Archive));
+        }
+
+        [Fact]
+        public void Single_slot_archive_is_replaced_by_the_next_rollover()
+        {
+            // LogMaxHistory <= 1: IME deletes _X.log and renames X.log to it.
+            var tracker = TrackerWithBookmark(Underscore, "A", 9000);
+            tracker.Reconcile(Ids((Underscore, "A"), (Live, "B")));
+            tracker.SetPosition(Live, 3000);
+
+            var moves = tracker.Reconcile(Ids((Underscore, "B"), (Live, "C")));
+
+            var move = Assert.Single(moves);
+            Assert.Equal(Live, move.From);
+            Assert.Equal(Underscore, move.To);
+            Assert.Equal(3000, tracker.GetPosition(Underscore));
+            Assert.Equal(0, tracker.GetPosition(Live));
+        }
+
+        [Fact]
+        public void A_renamed_file_can_leave_the_path_it_moved_into()
+        {
+            var tracker = TrackerWithBookmark(Live, "A", 3000);
+            tracker.Reconcile(Ids((Live, "A"), (Underscore, "B")));
+            tracker.SetPosition(Underscore, 700);
+
+            var moves = tracker.Reconcile(Ids((Underscore, "A"), (Archive, "B"), (Live, "C")));
+
+            Assert.Equal(2, moves.Count);
+            Assert.Equal(3000, tracker.GetPosition(Underscore));
+            Assert.Equal(700, tracker.GetPosition(Archive));
+            Assert.Equal(0, tracker.GetPosition(Live));
+        }
+
+        [Fact]
+        public void Behind_bookmark_only_when_smaller_than_the_position()
+        {
+            var tracker = TrackerWithBookmark(Live, "A", 3000);
+
+            Assert.True(tracker.IsBehindBookmark(Live, 2999));
+            Assert.False(tracker.IsBehindBookmark(Live, 3000));
+            Assert.False(tracker.IsBehindBookmark(Archive, 0));
+        }
+
+        [Fact]
+        public void Restored_identity_is_used_to_find_a_rollover_during_the_downtime()
+        {
+            var tracker = new LogFilePositionTracker();
+            tracker.RestorePosition(Live, 3000, 3000);
+            tracker.RestoreFileId(Live, "A");
+
+            var moves = tracker.Reconcile(Ids((Archive, "A"), (Live, "B")));
+
+            Assert.Single(moves);
+            Assert.Equal(3000, tracker.GetPosition(Archive));
+            Assert.Equal(0, tracker.GetPosition(Live));
+        }
+    }
+}
@@ -2,11 +2,14 @@
 using System;
 using System.IO;
 using System.Threading;
+using System.Threading.Tasks;
 using AutopilotMonitor.Agent.V2.Core.Logging;
 using AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Office;
 using AutopilotMonitor.Agent.V2.Core.Tests.Harness;
 using Xunit;

+#pragma warning disable xUnit1031 // one test waits on tasks on purpose: a blocked call is the failure it looks for
+
 namespace AutopilotMonitor.Agent.V2.Core.Tests.Monitoring.Office
 {
    /// <summary>
@@ -148,6 +151,35 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Monitoring.Office
            Assert.Equal(afterDispose, Volatile.Read(ref raises)); // no raises after dispose
        }

+        [Fact]
+        public void Dispose_from_another_thread_returns_while_the_initial_scan_handler_is_running()
+        {
+            using var tmp = new TempDirectory();
+            LayDownCoreBinary(tmp.Path); // the initial scan in Start() finds it and raises
+            var watcher = new OfficeBinaryWatcher(tmp.Path, CoreBinaries, NewLogger(tmp.Path));
+
+            using var entered = new ManualResetEventSlim(false);
+            using var release = new ManualResetEventSlim(false);
+            watcher.BinaryAppeared += (_, __) => { entered.Set(); release.Wait(TimeSpan.FromSeconds(10)); };
+
+            var start = Task.Run(() => watcher.Start());
+            try
+            {
+                Assert.True(entered.Wait(TimeSpan.FromSeconds(5)), "initial scan did not raise");
+
+                var dispose = Task.Run(() => watcher.Dispose());
+
+                Assert.True(dispose.Wait(TimeSpan.FromSeconds(5)),
+                    "Dispose waited for the running handler: the watcher's lock is held while BinaryAppeared is raised");
+            }
+            finally
+            {
+                release.Set();
+                start.Wait(TimeSpan.FromSeconds(10));
+                watcher.Dispose();
+            }
+        }
+
        private static bool SpinUntil(Func<bool> condition, int timeoutMs)
        {
            var deadline = Environment.TickCount + timeoutMs;
@@ -0,0 +1,152 @@
+#nullable enable
+using System;
+using System.Collections.Generic;
+using System.Diagnostics;
+using System.Threading;
+using System.Threading.Tasks;
+using AutopilotMonitor.Agent.V2.Core.Logging;
+using AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Office;
+using AutopilotMonitor.Agent.V2.Core.Tests.Harness;
+using Xunit;
+
+#pragma warning disable xUnit1031 // the tests wait on tasks on purpose: a blocked call is the failure they look for
+
+namespace AutopilotMonitor.Agent.V2.Core.Tests.Monitoring.Office
+{
+    /// <summary>
+    /// <see cref="OfficeProcessWatcher"/> with stand-in worker processes handed in through the
+    /// startup probe (the WMI start trace is never armed here, as in the sibling watchers' tests).
+    /// Covers the worker window (started / stopped) and the two ways a worker's exit used to go
+    /// wrong: disposing the watcher while the exit is being delivered, and a worker that was
+    /// already gone when the watcher subscribed.
+    /// </summary>
+    [Collection("SerialThreading")] // Process.Exited is delivered on the shared ThreadPool
+    public sealed class OfficeProcessWatcherTests : IDisposable
+    {
+        private static readonly TimeSpan Timeout = TimeSpan.FromSeconds(10);
+
+        private readonly TempDirectory _tmp = new TempDirectory();
+        private readonly AgentLogger _logger;
+        private readonly List<Process> _spawned = new List<Process>();
+
+        public OfficeProcessWatcherTests()
+        {
+            _logger = new AgentLogger(_tmp.Path, AgentLogLevel.Info);
+        }
+
+        public void Dispose()
+        {
+            foreach (var p in _spawned)
+            {
+                try { if (!p.HasExited) p.Kill(); } catch { }
+                try { p.Dispose(); } catch { }
+            }
+            _tmp.Dispose();
+        }
+
+        /// <summary>A stand-in worker that blocks on stdin until killed.</summary>
+        private Process Spawn()
+        {
+            var p = Process.Start(new ProcessStartInfo("cmd.exe", "/c pause")
+            {
+                UseShellExecute = false,
+                RedirectStandardInput = true,
+                RedirectStandardOutput = true,
+                CreateNoWindow = true,
+            });
+            Assert.NotNull(p);
+            _spawned.Add(p!);
+            return p!;
+        }
+
+        /// <summary>A second handle on the same process — what the watcher would have opened itself.</summary>
+        private static Process HandleOn(Process child)
+        {
+            var handle = Process.GetProcessById(child.Id);
+            handle.EnableRaisingEvents = true;
+            return handle;
+        }
+
+        /// <summary>Starts the watcher with <paramref name="handle"/> as the one running worker.</summary>
+        private static void StartWith(OfficeProcessWatcher watcher, Process handle)
+        {
+            watcher.WorkerSource = () => new[] { handle };
+            watcher.Start(armWmi: false);
+        }
+
+        [Fact]
+        public void A_running_worker_is_reported_before_Start_returns_and_its_exit_closes_the_window()
+        {
+            using var watcher = new OfficeProcessWatcher(_logger, settleSeconds: 0);
+            using var started = new ManualResetEventSlim(false);
+            using var stopped = new ManualResetEventSlim(false);
+            watcher.Started += (_, __) => started.Set();
+            watcher.Stopped += (_, __) => stopped.Set();
+            var child = Spawn();
+
+            StartWith(watcher, HandleOn(child));
+
+            Assert.True(started.IsSet, "Started was not raised by the startup probe");
+            Assert.True(watcher.IsActive);
+
+            child.Kill();
+
+            Assert.True(stopped.Wait(Timeout), "Stopped was not raised after the last worker exited");
+            Assert.False(watcher.IsActive);
+        }
+
+        [Fact]
+        public void Dispose_returns_while_the_exit_of_a_tracked_worker_is_being_delivered()
+        {
+            var watcher = new OfficeProcessWatcher(_logger, settleSeconds: 0);
+            var child = Spawn();
+            var handle = HandleOn(child);
+
+            // Subscribed before the watcher, so .NET runs it first — and .NET holds its own lock on
+            // the Process object for as long as it delivers Exited.
+            using var delivering = new ManualResetEventSlim(false);
+            using var release = new ManualResetEventSlim(false);
+            handle.Exited += (_, __) => { delivering.Set(); release.Wait(Timeout); };
+            StartWith(watcher, handle);
+
+            Task dispose;
+            try
+            {
+                child.Kill();
+                Assert.True(delivering.Wait(Timeout), "the worker's exit was not delivered");
+
+                dispose = Task.Run(() => watcher.Dispose());
+                Thread.Sleep(300); // let Dispose reach the Process object
+            }
+            finally
+            {
+                release.Set();
+            }
+
+            Assert.True(dispose.Wait(Timeout),
+                "Dispose and the exit delivery blocked each other: the Process is disposed under the watcher's lock");
+        }
+
+        [Fact]
+        public void A_worker_that_was_already_gone_when_the_watcher_subscribed_still_closes_the_window()
+        {
+            using var watcher = new OfficeProcessWatcher(_logger, settleSeconds: 0);
+            using var stopped = new ManualResetEventSlim(false);
+            watcher.Stopped += (_, __) => stopped.Set();
+
+            var child = Spawn();
+            var handle = HandleOn(child);
+            using var exitDelivered = new ManualResetEventSlim(false);
+            handle.Exited += (_, __) => exitDelivered.Set();
+            child.Kill();
+            // .NET raises Exited once per Process object. After this, a later subscriber never hears it.
+            Assert.True(exitDelivered.Wait(Timeout), "the stand-in's exit was not delivered");
+
+            StartWith(watcher, handle);
+
+            Assert.True(stopped.Wait(Timeout),
+                "the window never closed: the worker exited before the watcher subscribed to Exited");
+            Assert.False(watcher.IsActive);
+        }
+    }
+}
@@ -0,0 +1,199 @@
+#nullable enable
+using System;
+using System.Threading;
+using System.Threading.Tasks;
+using AutopilotMonitor.Agent.V2.Core.Logging;
+using AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Office;
+using AutopilotMonitor.Agent.V2.Core.Tests.Harness;
+using Microsoft.Win32;
+using Xunit;
+
+#pragma warning disable xUnit1031 // the tests wait on tasks on purpose: a blocked call is the failure they look for
+
+namespace AutopilotMonitor.Agent.V2.Core.Tests.Monitoring.Office
+{
+    /// <summary>
+    /// <see cref="RegistryChangeWatcher"/> against a real key under HKCU (no elevation needed).
+    /// The watcher's lock is a leaf lock: <c>Changed</c> is raised with the lock free, so a
+    /// handler can take other locks or dispose the watcher, and <c>Dispose</c> never waits for a
+    /// handler. One handler runs at a time, and a change that arrives while it runs is reported
+    /// after it returns.
+    /// </summary>
+    [Collection("SerialThreading")] // callbacks arrive on the shared ThreadPool
+    public sealed class RegistryChangeWatcherTests : IDisposable
+    {
+        private const string RootSubKey = @"SOFTWARE\AutopilotMonitor.Tests\OfficeRegistryChangeWatcher";
+        private const string TargetSubKey = RootSubKey + @"\Target";
+        private const uint RegNotifyThreadAgnostic = 0x10000000;
+        private static readonly TimeSpan Timeout = TimeSpan.FromSeconds(10);
+
+        private readonly TempDirectory _tmp = new TempDirectory();
+        private readonly AgentLogger _logger;
+
+        public RegistryChangeWatcherTests()
+        {
+            _logger = new AgentLogger(_tmp.Path, AgentLogLevel.Info);
+            DeleteTestKeys();
+            using (var root = Registry.CurrentUser.CreateSubKey(RootSubKey)) Assert.NotNull(root);
+        }
+
+        public void Dispose()
+        {
+            DeleteTestKeys();
+            _tmp.Dispose();
+        }
+
+        private static void DeleteTestKeys()
+        {
+            try { Registry.CurrentUser.DeleteSubKeyTree(RootSubKey, throwOnMissingSubKey: false); }
+            catch { /* teardown noise must not fail a test */ }
+        }
+
+        private static void CreateTarget()
+        {
+            using (var key = Registry.CurrentUser.CreateSubKey(TargetSubKey)) Assert.NotNull(key);
+        }
+
+        private static void WriteValue(string name)
+        {
+            using (var key = Registry.CurrentUser.OpenSubKey(TargetSubKey, writable: true))
+            {
+                Assert.NotNull(key);
+                key!.SetValue(name, Guid.NewGuid().ToString("N"));
+            }
+        }
+
+        private RegistryChangeWatcher NewWatcher() =>
+            new RegistryChangeWatcher(RegistryHive.CurrentUser, TargetSubKey, _logger);
+
+        [Fact]
+        public void Changed_fires_when_a_value_is_written_under_the_target()
+        {
+            CreateTarget();
+            using var watcher = NewWatcher();
+            using var fired = new ManualResetEventSlim(false);
+            watcher.Changed += (_, __) => fired.Set();
+
+            watcher.Start();
+            WriteValue("Probe");
+
+            Assert.True(fired.Wait(Timeout), "Changed did not fire for a value write under the target key");
+        }
+
+        [Fact]
+        public void Changed_fires_once_a_missing_target_key_appears()
+        {
+            using var watcher = NewWatcher();
+            using var fired = new ManualResetEventSlim(false);
+            watcher.Changed += (_, __) => fired.Set();
+
+            watcher.Start(); // target absent: watches the parent for a new child key
+            CreateTarget();
+
+            Assert.True(fired.Wait(Timeout), "Changed did not fire when the target key appeared");
+        }
+
+        [Fact]
+        public void Dispose_from_another_thread_returns_while_a_handler_is_running()
+        {
+            CreateTarget();
+            var watcher = NewWatcher();
+            using var entered = new ManualResetEventSlim(false);
+            using var release = new ManualResetEventSlim(false);
+            watcher.Changed += (_, __) => { entered.Set(); release.Wait(Timeout); };
+
+            try
+            {
+                watcher.Start();
+                WriteValue("Probe");
+                Assert.True(entered.Wait(Timeout), "handler was not invoked");
+
+                var dispose = Task.Run(() => watcher.Dispose());
+
+                Assert.True(dispose.Wait(TimeSpan.FromSeconds(5)),
+                    "Dispose waited for the running handler: the watcher's lock is held while Changed is raised");
+            }
+            finally
+            {
+                release.Set();
+                watcher.Dispose();
+            }
+        }
+
+        [Fact]
+        public void A_handler_may_dispose_its_own_watcher()
+        {
+            CreateTarget();
+            var watcher = NewWatcher();
+            using var disposedInHandler = new ManualResetEventSlim(false);
+            int calls = 0;
+            watcher.Changed += (_, __) =>
+            {
+                Interlocked.Increment(ref calls);
+                watcher.Dispose();
+                disposedInHandler.Set();
+            };
+
+            watcher.Start();
+            WriteValue("First");
+            Assert.True(disposedInHandler.Wait(Timeout), "handler did not return from disposing its watcher");
+
+            WriteValue("Second");
+            Thread.Sleep(300);
+            Assert.Equal(1, Volatile.Read(ref calls)); // a disposed watcher stays quiet
+        }
+
+        [Fact]
+        public void Handlers_never_overlap_and_a_change_during_a_handler_is_reported_after_it()
+        {
+            CreateTarget();
+            using var watcher = NewWatcher();
+            using var firstEntered = new ManualResetEventSlim(false);
+            using var release = new ManualResetEventSlim(false);
+            using var second = new ManualResetEventSlim(false);
+            int calls = 0, running = 0, maxRunning = 0;
+            watcher.Changed += (_, __) =>
+            {
+                var now = Interlocked.Increment(ref running);
+                int seen;
+                while (now > (seen = Volatile.Read(ref maxRunning)))
+                    Interlocked.CompareExchange(ref maxRunning, now, seen);
+
+                if (Interlocked.Increment(ref calls) == 1)
+                {
+                    firstEntered.Set();
+                    release.Wait(Timeout);
+                }
+                else
+                {
+                    second.Set();
+                }
+                Interlocked.Decrement(ref running);
+            };
+
+            watcher.Start();
+            WriteValue("First");
+            Assert.True(firstEntered.Wait(Timeout), "handler was not invoked");
+
+            WriteValue("DuringHandler");
+            Thread.Sleep(300);
+            Assert.Equal(1, Volatile.Read(ref calls)); // no second handler while the first runs
+
+            release.Set();
+
+            Assert.True(second.Wait(Timeout), "the change that arrived during the handler was never reported");
+            Assert.Equal(1, Volatile.Read(ref maxRunning));
+        }
+
+        [Fact]
+        public void Target_watch_is_not_tied_to_the_arming_thread()
+        {
+            using var watcher = NewWatcher();
+
+            // Re-arming happens on rotating ThreadPool threads. Without this flag Windows signals
+            // the event when such a thread ends, which looks like a change that never happened.
+            Assert.True((watcher.EffectivePrimaryFilter & RegNotifyThreadAgnostic) != 0,
+                "the target watch must carry REG_NOTIFY_THREAD_AGNOSTIC");
+        }
+    }
+}
@@ -0,0 +1,97 @@
+#nullable enable
+using System;
+using System.Security.Principal;
+using System.Threading;
+using System.Threading.Tasks;
+using AutopilotMonitor.Agent.V2.Core.Logging;
+using AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals;
+using AutopilotMonitor.Agent.V2.Core.Tests.Harness;
+using Microsoft.Win32;
+using Xunit;
+
+#pragma warning disable xUnit1031 // the test waits on a task on purpose: a blocked call is the failure it looks for
+
+namespace AutopilotMonitor.Agent.V2.Core.Tests.Monitoring.SystemSignals
+{
+    /// <summary>
+    /// <see cref="RealmJoinWatcher.Stop"/> while the "RealmJoin key appeared" callback is in
+    /// flight. The callback runs on a real registry watcher over the signed-in user's
+    /// <c>HKU\&lt;sid&gt;\SOFTWARE</c> (writable without elevation); the key probes are injected.
+    /// </summary>
+    [Collection("SerialThreading")] // registry callbacks arrive on the shared ThreadPool
+    public sealed class RealmJoinWatcherStopTests : IDisposable
+    {
+        private static readonly TimeSpan Timeout = TimeSpan.FromSeconds(10);
+
+        private readonly TempDirectory _tmp = new TempDirectory();
+        // A new direct child of HKCU\SOFTWARE is what the parent watch reacts to.
+        private readonly string _probeKey = @"SOFTWARE\AutopilotMonitor.Tests.RealmJoinStop." + Guid.NewGuid().ToString("N");
+
+        public void Dispose()
+        {
+            try { Registry.CurrentUser.DeleteSubKeyTree(_probeKey, throwOnMissingSubKey: false); }
+            catch { /* teardown noise must not fail a test */ }
+            _tmp.Dispose();
+        }
+
+        [Fact]
+        public void Stop_returns_while_the_key_appeared_callback_is_running()
+        {
+            var sid = WindowsIdentity.GetCurrent().User!.Value;
+            var userRealmJoinPath = sid + "\\" + RealmJoinInfo.UserRealmJoinSubPath;
+
+            var appearedProbe = new ManualResetEventSlim(false);
+            var release = new ManualResetEventSlim(false);
+            int armed = 0;
+            bool KeyExists(RegistryHive hive, string subPath)
+            {
+                // Everything is "absent" while the watcher arms. Afterwards the user-scope
+                // RealmJoin key "exists": the callback sees it and goes on to switch watchers.
+                if (hive != RegistryHive.Users || subPath != userRealmJoinPath || Volatile.Read(ref armed) == 0)
+                    return false;
+                appearedProbe.Set();
+                release.Wait(Timeout);
+                return true;
+            }
+
+            var watcher = new RealmJoinWatcher(
+                new AgentLogger(_tmp.Path, AgentLogLevel.Info),
+                enumeratePackageIds: (_, __) => Array.Empty<string>(),
+                tryReadPackage: (RegistryHive _, string __, string ___, out RealmJoinPackageSnapshot snapshot) =>
+                {
+                    snapshot = default!;
+                    return false;
+                },
+                keyExists: KeyExists,
+                readVersionInfo: () => default,
+                readUninstallDisplayVersion: () => null,
+                readDeploymentPhase: () => null);
+
+            // Production order: the SID is recorded, then RealmJoin reaches the running phase and
+            // the watcher arms its parent watch on HKU\<sid>\SOFTWARE.
+            watcher.ArmHku(sid);
+            watcher.TriggerNotifyRealmJoinPresenceFromTest(RealmJoinInfo.PhaseRunningThresholdMin);
+            Volatile.Write(ref armed, 1);
+
+            Task stop;
+            try
+            {
+                using (var key = Registry.CurrentUser.CreateSubKey(_probeKey)) Assert.NotNull(key);
+                Assert.True(appearedProbe.Wait(Timeout), "the parent watch did not report the new key");
+
+                stop = Task.Run(() => watcher.Stop());
+                Thread.Sleep(300); // let Stop reach the registry watcher whose callback is parked
+            }
+            finally
+            {
+                release.Set();
+            }
+
+            var returned = stop.Wait(Timeout);
+            // A blocked Stop holds the watcher's lock for good; disposing it would hang the run.
+            if (returned) watcher.Dispose();
+            Assert.True(returned,
+                "Stop and the key-appeared callback blocked each other: watchers are disposed under the state lock");
+        }
+    }
+}
@@ -80,6 +80,29 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Monitoring.Transport
            Assert.Equal(2, client.Calls);
        }

+        [Fact]
+        public async Task Registration_session_gone_report_is_exempt_from_the_cooldown_like_the_telemetry_one()
+        {
+            // The integrity report goes out post-config, seconds before the registration is refused.
+            var clock = Clock();
+            var client = new FakeApiClient();
+            client.Results.Enqueue(true);
+            client.Results.Enqueue(true);
+            var reporter = Reporter(client, clock);
+
+            await reporter.TrySendAsync(AgentErrorType.IntegrityCheckFailed, "m");
+            clock.Advance(TimeSpan.FromSeconds(5));
+            await reporter.TrySendAsync(AgentErrorType.RegistrationRejectedSessionGone, "m", httpStatusCode: 410);
+
+            Assert.Equal(2, client.Calls);
+            Assert.Equal(AgentErrorType.RegistrationRejectedSessionGone, client.Reports[1].ErrorType);
+            Assert.Equal(410, client.Reports[1].HttpStatusCode);
+
+            // Key dedup still applies: a second one is held back.
+            await reporter.TrySendAsync(AgentErrorType.RegistrationRejectedSessionGone, "m", httpStatusCode: 410);
+            Assert.Equal(2, client.Calls);
+        }
+
        [Fact]
        public async Task Second_session_unknown_report_within_the_window_is_still_suppressed()
        {
@@ -27,6 +27,9 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Orchestration
    ///     already in flight misses its wake.</item>
    ///   <item>DesktopArrivalHost before AadJoinHost — the AadJoinHost ctor takes the desktop
    ///     host's RequestResetForRealUserSwitch callback, so the target must exist first.</item>
+    ///   <item>UserEspKeepAwakeHost before RealmJoinHost — after an agent restart the RealmJoin
+    ///     watcher posts realmjoin_detected from its own Start; the keep-awake host hands its
+    ///     hold over to RealmJoin (D-413) and must already observe the rail.</item>
    /// </list>
    /// </summary>
    public sealed class DefaultComponentFactoryOrderingTests : IDisposable
@@ -143,6 +146,30 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Orchestration
            }
        }

+        [Fact]
+        public void Keep_awake_host_subscribes_before_the_RealmJoin_watcher_starts()
+        {
+            var hosts = CreateSurfaces(new AnalyzerConfiguration
+            {
+                EnableRealmJoinWatcher = true,
+                KeepAwakeDuringUserEsp = true,
+            }).Hosts;
+            try
+            {
+                AssertBefore<UserEspKeepAwakeHost, RealmJoinHost>(
+                    hosts,
+                    "D-413 — a realmjoin_detected posted from the watcher's Start (agent restart with " +
+                    "RealmJoin installed) must reach the keep-awake host, or it waits for a start it missed.");
+            }
+            finally
+            {
+                foreach (var host in hosts)
+                {
+                    try { host.Dispose(); } catch { /* construction-only test — best-effort cleanup */ }
+                }
+            }
+        }
+
        [Theory]
        [InlineData(false, 0)]
        [InlineData(true, 1)]
@@ -0,0 +1,158 @@
+#nullable enable
+using System;
+using System.Collections.Generic;
+using System.Linq;
+using System.Threading;
+using System.Threading.Tasks;
+using AutopilotMonitor.Agent.V2.Core.Logging;
+using AutopilotMonitor.Agent.V2.Core.Orchestration;
+using AutopilotMonitor.Agent.V2.Core.Tests.Harness;
+using AutopilotMonitor.Agent.V2.Core.Transport.Telemetry;
+using AutopilotMonitor.DecisionCore.Engine;
+using AutopilotMonitor.DecisionCore.State;
+using AutopilotMonitor.Shared.Models;
+using Newtonsoft.Json.Linq;
+using Xunit;
+
+#pragma warning disable xUnit1031 // the tests wait on tasks on purpose: a call that never returns is the failure they look for
+
+namespace AutopilotMonitor.Agent.V2.Core.Tests.Orchestration
+{
+    /// <summary>
+    /// Stopping the collector hosts is bounded per host: termination reaches the diagnostics
+    /// upload and the cleanup whatever a collector does. A host that hangs is left behind, named
+    /// in one <c>agent_trace</c>, and never called again; every other host is stopped and disposed
+    /// as before.
+    /// </summary>
+    [Collection("SerialThreading")]
+    public sealed class EnrollmentOrchestratorCollectorStopTests
+    {
+        private static readonly TimeSpan Bound = TimeSpan.FromMilliseconds(400);
+        private static readonly TimeSpan Wait = TimeSpan.FromSeconds(10);
+
+        private sealed class Host : ICollectorHost
+        {
+            private readonly List<string> _order;
+            private readonly ManualResetEventSlim? _hangUntil;
+            private readonly Exception? _throwOnStop;
+            private int _stopCalls;
+            private int _disposeCalls;
+
+            public Host(string name, List<string> order, ManualResetEventSlim? hangUntil = null, Exception? throwOnStop = null)
+            {
+                Name = name;
+                _order = order;
+                _hangUntil = hangUntil;
+                _throwOnStop = throwOnStop;
+            }
+
+            public string Name { get; }
+            public int StopCalls => Volatile.Read(ref _stopCalls);
+            public int DisposeCalls => Volatile.Read(ref _disposeCalls);
+
+            public void Start() { }
+
+            public void Stop()
+            {
+                Interlocked.Increment(ref _stopCalls);
+                lock (_order) _order.Add(Name);
+                if (_throwOnStop != null) throw _throwOnStop;
+                _hangUntil?.Wait();
+            }
+
+            public void Dispose() => Interlocked.Increment(ref _disposeCalls);
+        }
+
+        private sealed class Factory : IComponentFactory
+        {
+            private readonly IReadOnlyList<ICollectorHost> _hosts;
+            public Factory(IReadOnlyList<ICollectorHost> hosts) { _hosts = hosts; }
+
+            public CollectorSurfaces CreateCollectorHosts(
+                string sessionId,
+                string tenantId,
+                AgentLogger logger,
+                IReadOnlyCollection<string> whiteGloveSealingPatternIds,
+                ISignalIngressSink ingress,
+                IClock clock,
+                ITelemetrySpool? telemetrySpool,
+                TimelineEventStream? timelineEvents = null,
+                Func<DecisionState?>? decisionStateProbe = null) => new CollectorSurfaces(_hosts);
+        }
+
+        private static JObject? StopTimeoutEvent(EnrollmentOrchestrator sut) =>
+            sut.SpoolForTests!.Peek(1000)
+                .Where(i => i.Kind == TelemetryItemKind.Event && i.PayloadJson.Contains("collector_host_stop_timeout"))
+                .Select(i => JObject.Parse(i.PayloadJson))
+                .FirstOrDefault();
+
+        [Fact]
+        public void A_host_that_hangs_in_Stop_is_left_behind_and_the_others_are_still_stopped()
+        {
+            using var rig = new EnrollmentOrchestratorRig();
+            using var release = new ManualResetEventSlim(false);
+            var order = new List<string>();
+            var before = new Host("Before", order);
+            var hanging = new Host("Hanging", order, hangUntil: release);
+            var after = new Host("After", order);
+            var sut = rig.Build(
+                componentFactory: new Factory(new ICollectorHost[] { before, hanging, after }),
+                collectorHostStopTimeout: Bound);
+            sut.Start();
+
+            try
+            {
+                var stop = Task.Run(() => sut.StopCollectorHosts());
+
+                Assert.True(stop.Wait(Wait), "StopCollectorHosts never returned although one host hangs");
+                Assert.Equal(new[] { "Before", "Hanging", "After" }, order.ToArray());
+
+                JObject? evt = null;
+                Assert.True(SpinWait.SpinUntil(() => (evt = StopTimeoutEvent(sut)) != null, Wait),
+                    "the hanging host was not reported");
+                Assert.Equal("agent_trace", (string?)evt!["EventType"]);
+                var data = (JObject)evt["Data"]!;
+                Assert.Equal("collector_host_stop_timeout", (string?)data["decision"]);
+                Assert.Equal("Hanging", (string?)data["host"]);
+                Assert.Equal(1, (int)data["timeoutSeconds"]!);
+
+                // Stop() afterwards: the stuck host is not touched again, the others are disposed.
+                var fullStop = Task.Run(() => sut.Stop());
+                Assert.True(fullStop.Wait(Wait), "Stop never returned");
+                Assert.Equal(1, before.DisposeCalls);
+                Assert.Equal(0, hanging.DisposeCalls);
+                Assert.Equal(1, after.DisposeCalls);
+                Assert.Equal(1, hanging.StopCalls);
+            }
+            finally
+            {
+                release.Set();
+            }
+        }
+
+        [Fact]
+        public void Healthy_hosts_are_stopped_and_disposed_in_order_without_a_report()
+        {
+            using var rig = new EnrollmentOrchestratorRig();
+            var order = new List<string>();
+            var first = new Host("First", order);
+            var throwing = new Host("Throwing", order, throwOnStop: new InvalidOperationException("boom"));
+            var last = new Host("Last", order);
+            var hosts = new[] { first, throwing, last };
+            var sut = rig.Build(componentFactory: new Factory(hosts)); // default bound: nothing here comes near it
+            sut.Start();
+
+            sut.StopCollectorHosts();
+            sut.StopCollectorHosts(); // idempotent
+
+            Assert.Equal(new[] { "First", "Throwing", "Last" }, order.ToArray());
+            Assert.All(hosts, h => Assert.Equal(1, h.StopCalls));
+
+            Thread.Sleep(200);
+            Assert.Null(StopTimeoutEvent(sut));
+
+            sut.Stop();
+            Assert.All(hosts, h => Assert.Equal(1, h.DisposeCalls));
+        }
+    }
+}
@@ -0,0 +1,174 @@
+#nullable enable
+using System;
+using System.IO;
+using System.Linq;
+using System.Threading;
+using System.Threading.Tasks;
+using AutopilotMonitor.Agent.V2.Core.Logging;
+using AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Office;
+using AutopilotMonitor.Agent.V2.Core.Orchestration;
+using AutopilotMonitor.Agent.V2.Core.Tests.Harness;
+using AutopilotMonitor.DecisionCore.Engine;
+using AutopilotMonitor.Shared;
+using Microsoft.Win32;
+using Xunit;
+
+#pragma warning disable xUnit1031 // the tests wait on tasks on purpose: a blocked call is the failure they look for
+
+namespace AutopilotMonitor.Agent.V2.Core.Tests.Orchestration
+{
+    /// <summary>
+    /// <see cref="OfficeInstallDetectorHost"/> with its real watchers: the registry watcher on a
+    /// key under HKCU, the binary watcher on a temp folder, snapshots injected. Stopping the host
+    /// must never wait for a watcher callback, and a completion that coincides with a registry
+    /// callback must not leave the host unable to stop.
+    /// </summary>
+    [Collection("SerialThreading")] // registry + filesystem callbacks arrive on the shared ThreadPool
+    public sealed class OfficeInstallDetectorHostTests : IDisposable
+    {
+        private const string RegistrySubKey = @"SOFTWARE\AutopilotMonitor.Tests\OfficeInstallDetectorHost";
+        private static readonly DateTime At = new DateTime(2026, 11, 10, 9, 0, 0, DateTimeKind.Utc);
+        private static readonly TimeSpan Timeout = TimeSpan.FromSeconds(10);
+
+        private readonly TempDirectory _tmp = new TempDirectory();
+        private readonly FakeSignalIngressSink _sink = new FakeSignalIngressSink();
+        private readonly string _installPath;
+        private Func<OfficeC2RSnapshot> _snapshot;
+
+        public OfficeInstallDetectorHostTests()
+        {
+            DeleteTestKey();
+            using (var key = Registry.CurrentUser.CreateSubKey(RegistrySubKey)) Assert.NotNull(key);
+            _installPath = Path.Combine(_tmp.Path, "Office");
+            Directory.CreateDirectory(_installPath);
+            _snapshot = Idle;
+        }
+
+        public void Dispose()
+        {
+            DeleteTestKey();
+            _tmp.Dispose();
+        }
+
+        private static void DeleteTestKey()
+        {
+            try { Registry.CurrentUser.DeleteSubKeyTree(RegistrySubKey, throwOnMissingSubKey: false); }
+            catch { /* teardown noise must not fail a test */ }
+        }
+
+        private static void TouchRegistry()
+        {
+            using (var key = Registry.CurrentUser.OpenSubKey(RegistrySubKey, writable: true))
+            {
+                Assert.NotNull(key);
+                key!.SetValue("Probe", Guid.NewGuid().ToString("N"));
+            }
+        }
+
+        private OfficeInstallDetectorHost NewHost() =>
+            new OfficeInstallDetectorHost(
+                sessionId: "S1",
+                tenantId: "T1",
+                ingress: _sink,
+                clock: new VirtualClock(At),
+                logger: new AgentLogger(_tmp.Path, AgentLogLevel.Info),
+                settleSeconds: 0,
+                statePersistence: null,
+                resumeState: null,
+                registryHive: RegistryHive.CurrentUser,
+                registrySubKey: RegistrySubKey,
+                snapshotProvider: () => _snapshot());
+
+        // No install scenario, no install path: the detector stays idle and the host keeps
+        // raising OfficeExpected on registry changes.
+        private static OfficeC2RSnapshot Idle() => new OfficeC2RSnapshot { ConfigurationKeyPresent = true };
+
+        private OfficeC2RSnapshot Installing()
+        {
+            var s = new OfficeC2RSnapshot
+            {
+                ConfigurationKeyPresent = true,
+                ActiveScenarioPresent = true,
+                ActiveScenarioName = "INSTALL",
+                InstallScenarioPresent = true,
+                InstallScenarioName = "INSTALL",
+                InstallationPath = _installPath,
+                VersionToReport = "16.0.1.1",
+            };
+            s.Products.Add("O365ProPlusRetail");
+            return s;
+        }
+
+        private int OfficeEvents(string eventType) => _sink.Posted.Count(p =>
+            p.Payload != null
+            && p.Payload.TryGetValue(SignalPayloadKeys.EventType, out var et)
+            && et == eventType);
+
+        [Fact]
+        public void Stop_returns_while_a_registry_handler_is_running()
+        {
+            var host = NewHost();
+            using var entered = new ManualResetEventSlim(false);
+            using var release = new ManualResetEventSlim(false);
+            host.OfficeExpected += (_, __) => { entered.Set(); release.Wait(Timeout); };
+
+            try
+            {
+                host.Start();
+                TouchRegistry();
+                Assert.True(entered.Wait(Timeout), "the registry change did not reach the host");
+
+                var stop = Task.Run(() => host.Stop());
+
+                Assert.True(stop.Wait(TimeSpan.FromSeconds(5)),
+                    "Stop waited for the running registry handler");
+            }
+            finally
+            {
+                release.Set();
+            }
+        }
+
+        [Fact]
+        public void A_completion_during_a_running_registry_handler_does_not_block_Stop()
+        {
+            var host = NewHost();
+            using var entered = new ManualResetEventSlim(false);
+            using var release = new ManualResetEventSlim(false);
+            host.OfficeExpected += (_, __) => { entered.Set(); release.Wait(Timeout); };
+
+            try
+            {
+                // 1) A registry callback is in flight (parked in the host's OfficeExpected handler).
+                host.Start();
+                TouchRegistry();
+                Assert.True(entered.Wait(Timeout), "the registry change did not reach the host");
+
+                // 2) The install starts and completes meanwhile: the binary watcher sees the core
+                //    binary, the detector reports completed, the host tears its watchers down.
+                _snapshot = Installing;
+                host.SubmitDoSample(new OfficeDoSample { JobCount = 1, FileSize = 100, TotalBytesDownloaded = 10 });
+                Assert.Equal(1, OfficeEvents(Constants.EventTypes.OfficeInstallStarted));
+
+                var versionDir = Path.Combine(_installPath, "root", "Office16");
+                Directory.CreateDirectory(versionDir);
+                File.WriteAllText(Path.Combine(versionDir, "EXCEL.EXE"), "stub");
+                Assert.True(
+                    SpinWait.SpinUntil(() => OfficeEvents(Constants.EventTypes.OfficeInstallCompleted) == 1, Timeout),
+                    "the install was not reported as completed");
+
+                // 3) The agent stops while that registry callback is still running.
+                var stop = Task.Run(() => host.Stop());
+
+                Assert.True(stop.Wait(TimeSpan.FromSeconds(5)),
+                    "Stop waited behind the completion's teardown, which waited for the running registry handler");
+            }
+            finally
+            {
+                release.Set();
+            }
+
+            Assert.Equal(1, OfficeEvents(Constants.EventTypes.OfficeInstallCompleted));
+        }
+    }
+}
@@ -0,0 +1,162 @@
+using System;
+using System.Collections.Generic;
+using System.IO;
+using System.Linq;
+using AutopilotMonitor.Agent.V2.Core.Logging;
+using AutopilotMonitor.Agent.V2.Core.Orchestration;
+using AutopilotMonitor.Agent.V2.Core.Tests.Harness;
+using AutopilotMonitor.Agent.V2.Core.Transport;
+using AutopilotMonitor.DecisionCore.Engine;
+using AutopilotMonitor.DecisionCore.Signals;
+using AutopilotMonitor.Shared;
+using AutopilotMonitor.Shared.Models;
+using Xunit;
+
+namespace AutopilotMonitor.Agent.V2.Core.Tests.Orchestration
+{
+    /// <summary>The watchers only listen on the real keys; settings are played in, none is changed.</summary>
+    public sealed class ProxySettingsHostTests : IDisposable
+    {
+        private readonly TempDirectory _tmp = new TempDirectory();
+        private readonly FakeSignalIngressSink _ingress = new FakeSignalIngressSink();
+        private readonly VirtualClock _clock = new VirtualClock(new DateTime(2026, 11, 2, 6, 53, 43, DateTimeKind.Utc));
+        private readonly AgentLogger _logger;
+        private readonly ProxyObserver _observer;
+        private ProxySettings _settings = new ProxySettings(true, null, null, null, null);
+        private string _route = "proxy.example.test:8080";
+
+        public ProxySettingsHostTests()
+        {
+            _logger = new AgentLogger(_tmp.Path, AgentLogLevel.Info);
+            _observer = new ProxyObserver(() => _settings, () => _route, _logger, _clock, TimeSpan.FromSeconds(30));
+            _observer.CaptureBaseline();
+        }
+
+        private ProxySettingsHost NewHost() => new ProxySettingsHost(_observer, _ingress, _clock, _logger);
+
+        private void SwitchToNoProxy()
+        {
+            _settings = new ProxySettings(false, null, null, null, null);
+            _route = "direct";
+        }
+
+        private List<FakeSignalIngressSink.PostedSignal> ProxyEvents() =>
+            _ingress.Posted
+                .Where(p => p.Kind == DecisionSignalKind.InformationalEvent
+                            && p.Payload != null
+                            && p.Payload.TryGetValue(SignalPayloadKeys.EventType, out var eventType)
+                            && eventType == Constants.EventTypes.ProxyConfiguration)
+                .ToList();
+
+        private string Log()
+        {
+            var text = string.Empty;
+            foreach (var file in Directory.EnumerateFiles(_tmp.Path, "*.log", SearchOption.AllDirectories))
+            {
+                using var stream = new FileStream(file, FileMode.Open, FileAccess.Read, FileShare.ReadWrite);
+                using var reader = new StreamReader(stream);
+                text += reader.ReadToEnd();
+            }
+            return text;
+        }
+
+        public void Dispose() => _tmp.Dispose();
+
+        [Fact]
+        public void A_change_goes_on_the_timeline_as_a_warning_with_what_moved()
+        {
+            using var host = NewHost();
+            host.Start();
+            SwitchToNoProxy();
+
+            _observer.CheckForChange();
+
+            var signal = Assert.Single(ProxyEvents());
+            Assert.Equal(nameof(EventSeverity.Warning), signal.Payload![SignalPayloadKeys.Severity]);
+            Assert.Equal("Proxy settings changed: IE settings of this account: auto-detect -> no proxy", signal.Payload[SignalPayloadKeys.Message]);
+
+            var data = Assert.IsAssignableFrom<IReadOnlyDictionary<string, object>>(signal.TypedPayload);
+            Assert.Equal("changed", data["trigger"]);
+            Assert.Equal("IE settings of this account: auto-detect -> no proxy", data["change"]);
+            Assert.Equal("direct", data["route"]);
+            Assert.Equal("Direct", data["proxyType"]);
+        }
+
+        [Fact]
+        public void A_change_between_the_baseline_and_the_start_is_noticed_at_the_start()
+        {
+            SwitchToNoProxy();
+
+            using var host = NewHost();
+            host.Start();
+
+            Assert.Single(ProxyEvents());
+        }
+
+        [Fact]
+        public void No_change_means_no_event()
+        {
+            using var host = NewHost();
+            host.Start();
+
+            _observer.CheckForChange();
+
+            Assert.Empty(ProxyEvents());
+        }
+
+        [Fact]
+        public void A_stopped_ingress_does_not_reach_the_upload_path()
+        {
+            using var host = NewHost();
+            host.Start();
+            _ingress.ThrowOnPost = new InvalidOperationException("SignalIngress has been stopped.");
+            SwitchToNoProxy();
+
+            _observer.OnSendFailed(TimeSpan.Zero);
+
+            Assert.Contains("uploads are failing", Log());
+        }
+
+        [Fact]
+        public void Stopping_while_uploads_fail_says_so_once()
+        {
+            var host = NewHost();
+            host.Start();
+            _observer.OnSendFailed(TimeSpan.Zero);
+
+            host.Stop();
+            host.Stop();
+            host.Dispose();
+
+            var log = Log();
+            var first = log.IndexOf("stopping with uploads still failing", StringComparison.Ordinal);
+            Assert.True(first >= 0);
+            Assert.Equal(-1, log.IndexOf("stopping with uploads still failing", first + 1, StringComparison.Ordinal));
+        }
+
+        [Fact]
+        public void A_change_after_the_stop_no_longer_posts()
+        {
+            var host = NewHost();
+            host.Start();
+            host.Stop();
+            SwitchToNoProxy();
+
+            _observer.CheckForChange();
+
+            Assert.Empty(ProxyEvents());
+            host.Dispose();
+        }
+
+        [Fact]
+        public void A_host_that_never_started_stays_silent_on_stop()
+        {
+            var host = NewHost();
+            _observer.OnSendFailed(TimeSpan.Zero);
+
+            host.Dispose();
+
+            Assert.DoesNotContain("stopping with uploads still failing", Log());
+        }
+    }
+}
@@ -8,6 +8,7 @@ using AutopilotMonitor.Agent.V2.Core.Persistence;
 using AutopilotMonitor.Agent.V2.Core.Tests.Harness;
 using AutopilotMonitor.DecisionCore.Engine;
 using AutopilotMonitor.DecisionCore.Signals;
+using SharedEventTypes = AutopilotMonitor.Shared.Constants.EventTypes;
 using Xunit;

 // ManualResetEventSlim.Wait inside the controller is driven deterministically here; SpinUntil is
@@ -52,10 +53,10 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Orchestration

        private AgentLogger NewLogger() => new AgentLogger(_tmp.Path);

-        private SignalIngress BuildIngress(VirtualClock clock) =>
+        private SignalIngress BuildIngress(VirtualClock clock, string signalLogName = "signal-log.jsonl") =>
            new SignalIngress(
                engine: new DecisionEngine(),
-                signalLog: new SignalLogWriter(_tmp.File("signal-log.jsonl")),
+                signalLog: new SignalLogWriter(_tmp.File(signalLogName)),
                traceCounter: new SessionTraceOrdinalProvider(),
                processor: new FakeDecisionStepProcessor(),
                clock: clock);
@@ -300,6 +301,365 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Orchestration
            ing.Stop();
        }

+        // -------- RealmJoin hand-over (D-413) --------
+
+        /// <summary>Records keep_awake_released payloads from the rail (posted on ThreadPool threads).</summary>
+        private sealed class ReleaseRecorder
+        {
+            private readonly object _lock = new object();
+            private readonly List<Dictionary<string, string>> _released = new List<Dictionary<string, string>>();
+
+            public ReleaseRecorder(SignalIngress ing) => ing.SignalPosted += OnPosted;
+
+            private void OnPosted(DecisionSignalKind kind, IReadOnlyDictionary<string, string>? payload)
+            {
+                if (kind != DecisionSignalKind.InformationalEvent || payload == null) return;
+                if (!payload.TryGetValue(SignalPayloadKeys.EventType, out var eventType)
+                    || eventType != SharedEventTypes.KeepAwakeReleased) return;
+                var copy = new Dictionary<string, string>(StringComparer.Ordinal);
+                foreach (var kv in payload) copy[kv.Key] = kv.Value;
+                lock (_lock) { _released.Add(copy); }
+            }
+
+            public List<Dictionary<string, string>> Snapshot()
+            {
+                lock (_lock) { return new List<Dictionary<string, string>>(_released); }
+            }
+        }
+
+        private static void PostRealmJoin(SignalIngress ing, DecisionSignalKind kind, int? phase)
+        {
+            var payload = new Dictionary<string, string>();
+            if (phase.HasValue) payload[DecisionEngine.RealmJoinPayloadKeys.DeploymentPhase] = phase.Value.ToString();
+            ing.Post(kind, At, "RealmJoinWatcher", Raw("rj"), payload: payload);
+        }
+
+        private UserEspKeepAwakeHost NewHost(
+            SignalIngress ing,
+            VirtualClock clock,
+            KeepAwakeController controller,
+            Func<bool>? progress = null,
+            TimeSpan? safetyCap = null,
+            TimeSpan? realmJoinWait = null,
+            StartupEventGate? gate = null) =>
+            new UserEspKeepAwakeHost(ing, clock, NewLogger(),
+                controller: controller,
+                safetyCapOverride: safetyCap,
+                espTimeoutProvider: () => null,
+                accountSetupProgressProbe: progress ?? (() => true),
+                realmJoinStartWaitOverride: realmJoinWait,
+                startupGate: gate);
+
+        [Fact]
+        public void Page_exit_with_RealmJoin_still_Blank_holds_until_RealmJoin_starts()
+        {
+            // The common RealmJoin shape: detected during the ESP, deployment starts after the
+            // user-ESP page closed. The gap in between is what the hold now covers.
+            var clock = new VirtualClock(At);
+            using var ing = BuildIngress(clock);
+            var recorder = new ReleaseRecorder(ing);
+            var api = new FakeKeepAwakeApi();
+            var controller = new KeepAwakeController(NewLogger(), api);
+            var host = NewHost(ing, clock, controller, realmJoinWait: TimeSpan.FromMinutes(5));
+
+            ing.Start();
+            host.Start();
+            PostAccountSetupPhase(ing);
+            Assert.True(WaitFor(() => api.PreventCount == 1));
+            PostRealmJoin(ing, DecisionSignalKind.RealmJoinDetected, 0);
+
+            PostEspExiting(ing);
+            Assert.True(WaitFor(() => host.AwaitingRealmJoinForTest), "the page exit must start the RealmJoin wait");
+            PostEspExiting(ing); // a repeated exit changes nothing
+            Assert.False(WaitFor(() => api.AllowCount > 0, 500), "the hold must outlive the page exit while RealmJoin is Blank");
+            Assert.True(controller.IsEngaged);
+
+            clock.Advance(TimeSpan.FromSeconds(90));
+            PostRealmJoin(ing, DecisionSignalKind.RealmJoinPhaseChanged, 101);
+
+            Assert.True(WaitFor(() => api.AllowCount == 1), "RealmJoin leaving Blank must release the hold");
+            Assert.True(WaitFor(() => recorder.Snapshot().Count == 1));
+            var released = recorder.Snapshot()[0];
+            Assert.Equal(UserEspKeepAwakeHost.ReasonRealmJoinStarted, released["reason"]);
+            Assert.Equal("90", released["waitedSeconds"]);
+
+            host.Dispose();
+            ing.Stop();
+        }
+
+        [Fact]
+        public void RealmJoin_wait_bound_releases_when_RealmJoin_never_starts()
+        {
+            // RealmJoin may never leave Blank in the session — the wait is bounded.
+            var clock = new VirtualClock(At);
+            using var ing = BuildIngress(clock);
+            var recorder = new ReleaseRecorder(ing);
+            var api = new FakeKeepAwakeApi();
+            var controller = new KeepAwakeController(NewLogger(), api);
+            var host = NewHost(ing, clock, controller, realmJoinWait: TimeSpan.FromMilliseconds(150));
+
+            ing.Start();
+            host.Start();
+            PostAccountSetupPhase(ing);
+            Assert.True(WaitFor(() => api.PreventCount == 1));
+            PostRealmJoin(ing, DecisionSignalKind.RealmJoinDetected, 0);
+            PostEspExiting(ing);
+
+            Assert.True(WaitFor(() => api.AllowCount == 1), "the RealmJoin wait must end the hold");
+            Assert.True(WaitFor(() => recorder.Snapshot().Count == 1));
+            var released = recorder.Snapshot()[0];
+            Assert.Equal(UserEspKeepAwakeHost.ReasonRealmJoinNotStarted, released["reason"]);
+            Assert.True(released.ContainsKey("waitMinutes"));
+
+            host.Dispose();
+            ing.Stop();
+        }
+
+        [Fact]
+        public void Page_exit_replaces_the_ESP_safety_cap_with_the_RealmJoin_wait()
+        {
+            // One timer, one bound per phase of the hold: once the page closed, the ESP-sized cap
+            // must not end the RealmJoin wait.
+            var clock = new VirtualClock(At);
+            using var ing = BuildIngress(clock);
+            var recorder = new ReleaseRecorder(ing);
+            var api = new FakeKeepAwakeApi();
+            var controller = new KeepAwakeController(NewLogger(), api);
+            var host = NewHost(ing, clock, controller,
+                safetyCap: TimeSpan.FromSeconds(1), realmJoinWait: TimeSpan.FromMinutes(5));
+
+            ing.Start();
+            host.Start();
+            PostRealmJoin(ing, DecisionSignalKind.RealmJoinDetected, 0);
+            PostAccountSetupPhase(ing);
+            Assert.True(WaitFor(() => api.PreventCount == 1));
+            PostEspExiting(ing);
+            Assert.True(WaitFor(() => host.AwaitingRealmJoinForTest));
+
+            Assert.False(WaitFor(() => api.AllowCount > 0, 1500), "the superseded ESP cap must not fire");
+
+            PostRealmJoin(ing, DecisionSignalKind.RealmJoinPhaseChanged, 101);
+            Assert.True(WaitFor(() => api.AllowCount == 1));
+            Assert.True(WaitFor(() => recorder.Snapshot().Count == 1));
+            Assert.Equal(UserEspKeepAwakeHost.ReasonRealmJoinStarted, recorder.Snapshot()[0]["reason"]);
+
+            host.Dispose();
+            ing.Stop();
+        }
+
+        [Fact]
+        public void Page_exit_without_RealmJoin_releases_as_before()
+        {
+            var clock = new VirtualClock(At);
+            using var ing = BuildIngress(clock);
+            var recorder = new ReleaseRecorder(ing);
+            var api = new FakeKeepAwakeApi();
+            var controller = new KeepAwakeController(NewLogger(), api);
+            var host = NewHost(ing, clock, controller, realmJoinWait: TimeSpan.FromMinutes(5));
+
+            ing.Start();
+            host.Start();
+            PostAccountSetupPhase(ing);
+            Assert.True(WaitFor(() => api.PreventCount == 1));
+            PostEspExiting(ing);
+
+            Assert.True(WaitFor(() => api.AllowCount == 1));
+            Assert.True(WaitFor(() => recorder.Snapshot().Count == 1));
+            Assert.Equal(UserEspKeepAwakeHost.ReasonUserEspExited, recorder.Snapshot()[0]["reason"]);
+            Assert.False(host.AwaitingRealmJoinForTest);
+
+            host.Dispose();
+            ing.Stop();
+        }
+
+        [Theory]
+        [InlineData(DecisionSignalKind.RealmJoinPhaseChanged, 100)]
+        [InlineData(DecisionSignalKind.RealmJoinPhaseChanged, 210)]
+        [InlineData(DecisionSignalKind.RealmJoinResolved, null)]
+        public void RealmJoin_leaving_Blank_before_the_page_exit_releases_the_hold(DecisionSignalKind kind, int? phase)
+        {
+            // RealmJoin can start shortly before the page closes; it keeps the device awake from
+            // there. Resolved carries no phase and still means "left Blank".
+            var clock = new VirtualClock(At);
+            using var ing = BuildIngress(clock);
+            var recorder = new ReleaseRecorder(ing);
+            var api = new FakeKeepAwakeApi();
+            var controller = new KeepAwakeController(NewLogger(), api);
+            var host = NewHost(ing, clock, controller, realmJoinWait: TimeSpan.FromMinutes(5));
+
+            ing.Start();
+            host.Start();
+            PostAccountSetupPhase(ing);
+            Assert.True(WaitFor(() => api.PreventCount == 1));
+            PostRealmJoin(ing, DecisionSignalKind.RealmJoinDetected, 0);
+            Assert.False(WaitFor(() => api.AllowCount > 0, 300), "detection alone must not release");
+
+            PostRealmJoin(ing, kind, phase);
+
+            Assert.True(WaitFor(() => api.AllowCount == 1));
+            Assert.True(WaitFor(() => recorder.Snapshot().Count == 1));
+            var released = recorder.Snapshot()[0];
+            Assert.Equal(UserEspKeepAwakeHost.ReasonRealmJoinStarted, released["reason"]);
+            Assert.False(released.ContainsKey("waitedSeconds"));
+
+            host.Dispose();
+            ing.Stop();
+        }
+
+        [Fact]
+        public void RealmJoin_already_deploying_before_AccountSetup_prevents_the_engage()
+        {
+            // Agent restart: the watcher reports the running phase from its start, and the
+            // AccountSetup phase is posted again afterwards — there is nothing to hand over.
+            var clock = new VirtualClock(At);
+            using var ing = BuildIngress(clock);
+            var api = new FakeKeepAwakeApi();
+            var controller = new KeepAwakeController(NewLogger(), api);
+            var host = NewHost(ing, clock, controller, realmJoinWait: TimeSpan.FromMinutes(5));
+
+            ing.Start();
+            host.Start();
+            PostRealmJoin(ing, DecisionSignalKind.RealmJoinDetected, 101);
+            PostAccountSetupPhase(ing);
+
+            Assert.False(WaitFor(() => api.PreventCount > 0, 500), "no hold once RealmJoin deploys");
+            Assert.False(controller.IsEngaged);
+
+            host.Dispose();
+            ing.Stop();
+        }
+
+        // -------- Page-closed latch across agent restarts (D-414) --------
+
+        /// <summary>
+        /// One agent run: its own ingress and host on the shared state folder. A later run is a new
+        /// <see cref="StartupEventGate"/> loading the same folder, exactly what a restart does.
+        /// </summary>
+        private sealed class AgentRun : IDisposable
+        {
+            public SignalIngress Ingress { get; }
+            public FakeKeepAwakeApi Api { get; } = new FakeKeepAwakeApi();
+            public KeepAwakeController Controller { get; }
+            public StartupEventGate Gate { get; }
+            public UserEspKeepAwakeHost Host { get; }
+
+            public AgentRun(UserEspKeepAwakeHostTests t, string stateDir, string runName, Func<bool> progress)
+            {
+                var clock = new VirtualClock(At);
+                Ingress = t.BuildIngress(clock, $"signal-log-{runName}.jsonl");
+                Controller = new KeepAwakeController(t.NewLogger(), Api);
+                Gate = new StartupEventGate(stateDir, t.NewLogger());
+                Host = t.NewHost(Ingress, clock, Controller, progress: progress,
+                    realmJoinWait: TimeSpan.FromMinutes(5), gate: Gate);
+                Ingress.Start();
+                Host.Start();
+            }
+
+            public void Dispose()
+            {
+                Host.Dispose();
+                Ingress.Stop();
+                Ingress.Dispose();
+            }
+        }
+
+        [Fact]
+        public void Closed_page_keeps_a_later_agent_run_from_engaging()
+        {
+            // After an agent restart the AccountSetup phase reaches the rail again (IME logs it at
+            // the next sign-in, the adapter's dedup lives per process). The page is gone, so no hold.
+            using var stateDir = new TempDirectory();
+            using (var first = new AgentRun(this, stateDir.Path, "1", () => true))
+            {
+                PostAccountSetupPhase(first.Ingress);
+                Assert.True(WaitFor(() => first.Api.PreventCount == 1));
+                PostEspExiting(first.Ingress);
+                Assert.True(WaitFor(() => first.Api.AllowCount == 1));
+                Assert.True(WaitFor(() => first.Gate.AlreadySucceeded(UserEspKeepAwakeHost.UserEspPageClosedKey)));
+            }
+
+            using var second = new AgentRun(this, stateDir.Path, "2", () => true);
+            PostAccountSetupPhase(second.Ingress);
+
+            Assert.False(WaitFor(() => second.Api.PreventCount > 0, 500), "the page already closed in this enrollment");
+            Assert.False(second.Controller.IsEngaged);
+        }
+
+        [Fact]
+        public void Restart_before_the_page_closed_engages_again()
+        {
+            // A reboot in the middle of the user ESP: the page is still to come, so the next run holds.
+            using var stateDir = new TempDirectory();
+            using (var first = new AgentRun(this, stateDir.Path, "1", () => true))
+            {
+                PostAccountSetupPhase(first.Ingress);
+                Assert.True(WaitFor(() => first.Api.PreventCount == 1));
+            }
+
+            using var second = new AgentRun(this, stateDir.Path, "2", () => true);
+            PostAccountSetupPhase(second.Ingress);
+
+            Assert.True(WaitFor(() => second.Api.PreventCount == 1), "the user ESP is still running");
+            Assert.True(second.Controller.IsEngaged);
+        }
+
+        [Fact]
+        public void Handoff_exit_without_AccountSetup_progress_sets_no_latch()
+        {
+            using var stateDir = new TempDirectory();
+            using (var first = new AgentRun(this, stateDir.Path, "1", () => false))
+            {
+                PostAccountSetupPhase(first.Ingress);
+                Assert.True(WaitFor(() => first.Api.PreventCount == 1));
+                PostEspExiting(first.Ingress); // the Device→Account handoff
+                Assert.False(WaitFor(() => first.Api.AllowCount > 0, 300));
+                Assert.False(first.Gate.AlreadySucceeded(UserEspKeepAwakeHost.UserEspPageClosedKey));
+            }
+
+            using var second = new AgentRun(this, stateDir.Path, "2", () => true);
+            PostAccountSetupPhase(second.Ingress);
+
+            Assert.True(WaitFor(() => second.Api.PreventCount == 1));
+        }
+
+        [Fact]
+        public void Page_exit_while_waiting_for_RealmJoin_is_latched()
+        {
+            // The hold outlived the page while RealmJoin was Blank, then the agent restarted: after
+            // the reboot RealmJoin needs the next sign-in anyway, so the next run does not hold.
+            using var stateDir = new TempDirectory();
+            using (var first = new AgentRun(this, stateDir.Path, "1", () => true))
+            {
+                PostRealmJoin(first.Ingress, DecisionSignalKind.RealmJoinDetected, 0);
+                PostAccountSetupPhase(first.Ingress);
+                Assert.True(WaitFor(() => first.Api.PreventCount == 1));
+                PostEspExiting(first.Ingress);
+                Assert.True(WaitFor(() => first.Host.AwaitingRealmJoinForTest));
+                Assert.True(WaitFor(() => first.Gate.AlreadySucceeded(UserEspKeepAwakeHost.UserEspPageClosedKey)));
+            }
+
+            using var second = new AgentRun(this, stateDir.Path, "2", () => true);
+            PostRealmJoin(second.Ingress, DecisionSignalKind.RealmJoinDetected, 0);
+            PostAccountSetupPhase(second.Ingress);
+
+            Assert.False(WaitFor(() => second.Api.PreventCount > 0, 500));
+        }
+
+        [Fact]
+        public void Page_exit_seen_while_idle_is_latched_and_blocks_a_later_engage()
+        {
+            // The exit counts in every hold state — here the host never engaged before it.
+            using var stateDir = new TempDirectory();
+            using var run = new AgentRun(this, stateDir.Path, "1", () => true);
+
+            PostEspExiting(run.Ingress);
+            Assert.True(WaitFor(() => run.Gate.AlreadySucceeded(UserEspKeepAwakeHost.UserEspPageClosedKey)),
+                "an exit seen while idle must still be latched");
+
+            PostAccountSetupPhase(run.Ingress);
+            Assert.False(WaitFor(() => run.Api.PreventCount > 0, 500));
+        }
+
        // -------- KeepAwakeController: late-confirm (ready-timeout) edge --------

        [Fact]
@@ -0,0 +1,167 @@
+#nullable enable
+using System;
+using System.Collections.Generic;
+using System.IO;
+using System.Threading.Tasks;
+using AutopilotMonitor.Agent.V2.Core.Configuration;
+using AutopilotMonitor.Agent.V2.Core.Logging;
+using AutopilotMonitor.Agent.V2.Core.Monitoring.Runtime;
+using AutopilotMonitor.Agent.V2.Core.Monitoring.Transport;
+using AutopilotMonitor.Agent.V2.Core.Orchestration;
+using AutopilotMonitor.Agent.V2.Core.Security;
+using AutopilotMonitor.Agent.V2.Core.Tests.Harness;
+using AutopilotMonitor.Agent.V2.Core.Tests.Orchestration;
+using AutopilotMonitor.Agent.V2.Runtime;
+using AutopilotMonitor.DecisionCore.Engine;
+using AutopilotMonitor.Shared.Models;
+using Xunit;
+using ProgramAlias = AutopilotMonitor.Agent.V2.Program;
+
+namespace AutopilotMonitor.Agent.V2.Core.Tests.Program
+{
+    /// <summary>
+    /// A registration the backend answered with HTTP 410 at process start: the session was deleted.
+    /// Exactly one <see cref="AgentErrorType.RegistrationRejectedSessionGone"/> report, then the
+    /// start-time end of monitoring with a forced cleanup — the same end state as the emergency
+    /// break and the kill signal. The WhiteGlove Part 2 start that registers a new session instead
+    /// is covered by <c>SessionRegistrationHelperTests</c>; here only its trace on <c>agent_started</c>.
+    /// </summary>
+    public sealed class SessionGoneAtRegistrationTests : IDisposable
+    {
+        private readonly TempDirectory _tmp = new TempDirectory();
+        private readonly AgentLogger _logger;
+        private readonly SessionIdPersistence _persistence;
+        private readonly string _stateDir;
+        private readonly List<string> _sequence = new List<string>();
+
+        public SessionGoneAtRegistrationTests()
+        {
+            _logger = new AgentLogger(Path.Combine(_tmp.Path, "logs"), AgentLogLevel.Info);
+            _persistence = new SessionIdPersistence(_tmp.Path);
+            _persistence.GetOrCreate(_logger);
+            _stateDir = Path.Combine(_tmp.Path, "State");
+        }
+
+        public void Dispose() => _tmp.Dispose();
+
+        private sealed class RecordingEmergencyReporter : EmergencyReporter
+        {
+            private readonly List<string> _sequence;
+            public List<(AgentErrorType ErrorType, string Message, int? HttpStatusCode, int Attempts)> Reports { get; } =
+                new List<(AgentErrorType, string, int?, int)>();
+
+            public RecordingEmergencyReporter(List<string> sequence)
+                : base(apiClient: null!, sessionId: "S1", tenantId: "T1", agentVersion: "0.0.0", logger: null!)
+            {
+                _sequence = sequence;
+            }
+
+            public override Task TrySendAsync(
+                AgentErrorType errorType,
+                string message,
+                int? httpStatusCode = null,
+                long? sequenceNumber = null,
+                int attempts = 1,
+                TimeSpan? perAttemptTimeout = null,
+                TimeSpan? retryDelay = null,
+                double? sessionAgeHours = null,
+                RegistrationFailureSummary? priorRegistrationFailure = null)
+            {
+                Reports.Add((errorType, message, httpStatusCode, attempts));
+                _sequence.Add("report");
+                return Task.CompletedTask;
+            }
+        }
+
+        private CleanupService CleanupFactory()
+        {
+            _sequence.Add("cleanup");
+            // The real factory spawns a PowerShell cleanup script; throwing makes the cleanup retry
+            // swallow and log it, so the call is counted without a side effect (as in ProgramGuardsTests).
+            throw new InvalidOperationException("test-harness: cleanup factory must not spawn real PowerShell in unit tests");
+        }
+
+        private bool MarkerExists => File.Exists(Path.Combine(_stateDir, "enrollment-complete.marker"));
+
+        [Theory]
+        [InlineData(true)]
+        [InlineData(false)] // forced like the kill signal: SelfDestructOnComplete does not gate it
+        public void Reports_once_then_ends_monitoring_with_a_forced_cleanup(bool selfDestructOnComplete)
+        {
+            _persistence.SaveWhiteGloveComplete(_logger);
+            var config = new AgentConfiguration { SessionId = "S1", TenantId = "T1", SelfDestructOnComplete = selfDestructOnComplete };
+            var reporter = new RecordingEmergencyReporter(_sequence);
+
+            var exitCode = BackendSessionRegistration.ConcludeSessionGone(
+                config, reporter, _persistence, _stateDir, CleanupFactory, consoleMode: false, _logger);
+
+            Assert.Equal(0, exitCode);
+            // The report leaves before the cleanup deletes the agent.
+            Assert.Equal(new[] { "report", "cleanup" }, _sequence);
+
+            var report = Assert.Single(reporter.Reports);
+            Assert.Equal(AgentErrorType.RegistrationRejectedSessionGone, report.ErrorType);
+            Assert.Equal(410, report.HttpStatusCode);
+            Assert.Contains("410", report.Message);
+            Assert.True(report.Attempts > 1, "the process ends right after: the one report gets a retry");
+
+            Assert.True(MarkerExists);
+            Assert.False(_persistence.SessionExists());
+            Assert.False(_persistence.IsWhiteGloveResume());
+            Assert.Null(_persistence.LoadSessionCreatedAt());
+            // The next start ends at the bootstrap guard, exactly as after the emergency break.
+            Assert.True(ProgramAlias.CheckEnrollmentCompleteMarker(
+                _stateDir, selfDestructOnComplete: false, cleanupServiceFactory: null, _logger, consoleMode: false));
+        }
+
+        [Fact]
+        public void Ends_monitoring_without_a_reporter()
+        {
+            var config = new AgentConfiguration { SessionId = "S1", TenantId = "T1" };
+
+            var exitCode = BackendSessionRegistration.ConcludeSessionGone(
+                config, emergencyReporter: null!, _persistence, _stateDir, CleanupFactory, consoleMode: false, _logger);
+
+            Assert.Equal(0, exitCode);
+            Assert.Equal(new[] { "cleanup" }, _sequence);
+            Assert.True(MarkerExists);
+            Assert.False(_persistence.SessionExists());
+        }
+
+        [Theory]
+        [InlineData(SessionRotationReasons.SessionGone)]
+        [InlineData(SessionRotationReasons.OwnerMismatch)]
+        public void Agent_started_names_why_the_session_was_rotated(string reason)
+        {
+            var data = EmitAgentStarted(rotatedFromSessionId: "11111111-1111-1111-1111-111111111111", reason);
+
+            Assert.Equal(true, data["sessionRotated"]);
+            Assert.Equal("11111111-1111-1111-1111-111111111111", data["previousSessionId"]);
+            Assert.Equal(reason, data["sessionRotationReason"]);
+        }
+
+        [Fact]
+        public void Agent_started_carries_no_rotation_reason_on_the_normal_path()
+        {
+            var data = EmitAgentStarted(rotatedFromSessionId: null, sessionRotationReason: null);
+
+            Assert.Equal(false, data["sessionRotated"]);
+            Assert.False(data.ContainsKey("sessionRotationReason"));
+        }
+
+        private Dictionary<string, object> EmitAgentStarted(string? rotatedFromSessionId, string? sessionRotationReason)
+        {
+            var sink = new FakeSignalIngressSink();
+            LifecycleEmitters.EmitAgentStarted(
+                new InformationalEventPost(sink, SystemClock.Instance, _logger),
+                new AgentConfiguration { SessionId = "S1", TenantId = "00000000-0000-0000-0000-000000000001", CommandLineArgs = string.Empty },
+                new ProgramAlias.PreviousExitSummary { ExitType = "reboot_kill" },
+                "2.0.test",
+                remoteConfigService: null,
+                _logger,
+                rotatedFromSessionId: rotatedFromSessionId,
+                sessionRotationReason: sessionRotationReason);
+            return (Dictionary<string, object>)Assert.Single(sink.Posted).TypedPayload!;
+        }
+    }
+}
@@ -7,7 +7,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Security
 {
    /// <summary>
    /// Regression coverage for the IsHybridJoin detection that runs at session-registration
-    /// time. Field evidence (session c4c8d206-…, Lenovo ThinkPad T14 Gen 5, Win11 23H2
+    /// time. Field evidence (Lenovo ThinkPad T14 Gen 5, Win11 23H2
    /// 22631.4317): the AutopilotPolicyCache key on this device exposes
    /// <c>CloudAssignedDomainJoinMethod</c> only inside the embedded <c>PolicyJsonCache</c>
    /// blob, not as a top-level registry value. Without the JSON fallback the agent registered
@@ -47,11 +47,11 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Security
        [Fact]
        public void Missing_TopLevel_falls_back_to_PolicyJsonCache_one_returns_true()
        {
-            // Real-world payload from the Bayer Lenovo T14 Gen 5 / Win11 23H2 22631.4317
-            // device that triggered this fix. Truncated for readability — the only relevant
+            // Shape of a real PolicyJsonCache payload (Win11 23H2 22631.4317) with a
+            // placeholder tenant domain. Truncated for readability — the only relevant
            // key is CloudAssignedDomainJoinMethod=1.
            const string policyJson =
-                "{\r\n  \"CloudAssignedTenantDomain\": \"bayergroup.onmicrosoft.com\",\r\n" +
+                "{\r\n  \"CloudAssignedTenantDomain\": \"contoso.onmicrosoft.com\",\r\n" +
                "  \"CloudAssignedDomainJoinMethod\": 1,\r\n" +
                "  \"AutopilotMode\": 2\r\n}";

@@ -166,6 +166,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Security
            Assert.Equal(0, tracker.ConsecutiveFailures);
            Assert.Equal(new[] { originalSessionId, rotatedTo }, seenSessionIds);
            Assert.Equal(originalSessionId, result.RotatedFromSessionId);
+            Assert.Equal(SessionRotationReasons.OwnerMismatch, result.RotationReason);
        }

        private static BackendRefusalException TenantConflict()
@@ -313,6 +314,136 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Security
            Assert.Equal(1, tracker.ConsecutiveFailures);
        }

+        // ── 410 at registration: the backend deleted the session ────────────
+
+        private static BackendSessionGoneException SessionGone()
+            => new BackendSessionGoneException("Backend returned 410 Gone: the session was deleted or is being deleted.", 410);
+
+        [Fact]
+        public async Task Session_gone_ends_the_run_at_once_without_retry_rotation_or_auth_failure()
+        {
+            using var tmp = new TempDirectory();
+            var logger = NewLogger(tmp);
+            var config = NewConfig();
+            var rotations = 0;
+
+            var apiClient = new FakeApiClient(_ => throw SessionGone());
+            var tracker = new AuthFailureTracker(maxFailures: 5, timeoutMinutes: 0,
+                clock: SystemClock.Instance, logger: logger);
+
+            // The rotation hook is wired on every start; without the Part 2 flag it must stay unused.
+            var result = await SessionRegistrationHelper.RegisterWithRetryAsync(
+                apiClient, config, agentVersion: "0.0.0", logger: logger,
+                authFailureTracker: tracker,
+                backoffDelay: _ => throw new InvalidOperationException("a 410 must not be retried"),
+                networkLinkWait: _ => Task.CompletedTask,
+                rotateSession: () => { rotations++; return Guid.NewGuid().ToString(); });
+
+            Assert.Equal(SessionRegistrationOutcome.SessionGone, result.Outcome);
+            Assert.Equal(410, result.HttpStatusCode);
+            Assert.Equal(1, apiClient.CallCount);
+            Assert.Equal(0, rotations);
+            Assert.Equal(0, tracker.ConsecutiveFailures);
+            Assert.Null(result.RotatedFromSessionId);
+            Assert.Null(result.RotationReason);
+        }
+
+        [Fact]
+        public async Task Session_gone_at_a_whiteglove_part2_start_rotates_once_and_registers_the_new_session()
+        {
+            using var tmp = new TempDirectory();
+            var logger = NewLogger(tmp);
+            var config = NewConfig();
+            var originalSessionId = config.SessionId;
+            var rotatedTo = Guid.NewGuid().ToString();
+            var seenSessionIds = new System.Collections.Generic.List<string>();
+            var rotations = 0;
+
+            var apiClient = new FakeApiClient(
+                attempt => attempt == 1
+                    ? throw SessionGone()
+                    : new RegisterSessionResponse { Success = true, SessionId = rotatedTo, ValidatedBy = ValidatorType.AutopilotV1 },
+                onRegister: r => seenSessionIds.Add(r.SessionId));
+            var tracker = new AuthFailureTracker(maxFailures: 5, timeoutMinutes: 0,
+                clock: SystemClock.Instance, logger: logger);
+
+            var result = await SessionRegistrationHelper.RegisterWithRetryAsync(
+                apiClient, config, agentVersion: "0.0.0", logger: logger,
+                authFailureTracker: tracker,
+                backoffDelay: _ => throw new InvalidOperationException("rotation must retry without backoff"),
+                networkLinkWait: _ => Task.CompletedTask,
+                rotateSession: () => { rotations++; config.SessionId = rotatedTo; return rotatedTo; },
+                rotateOnSessionGone: true);
+
+            Assert.Equal(SessionRegistrationOutcome.Succeeded, result.Outcome);
+            Assert.Equal(2, apiClient.CallCount);
+            Assert.Equal(1, rotations);
+            Assert.Equal(0, tracker.ConsecutiveFailures);
+            Assert.Equal(new[] { originalSessionId, rotatedTo }, seenSessionIds);
+            Assert.Equal(originalSessionId, result.RotatedFromSessionId);
+            Assert.Equal(SessionRotationReasons.SessionGone, result.RotationReason);
+        }
+
+        [Fact]
+        public async Task Second_session_gone_after_rotation_ends_the_run()
+        {
+            using var tmp = new TempDirectory();
+            var logger = NewLogger(tmp);
+            var config = NewConfig();
+            var rotations = 0;
+
+            var apiClient = new FakeApiClient(_ => throw SessionGone());
+
+            var result = await SessionRegistrationHelper.RegisterWithRetryAsync(
+                apiClient, config, agentVersion: "0.0.0", logger: logger,
+                backoffDelay: _ => throw new InvalidOperationException("a 410 must not be retried"),
+                networkLinkWait: _ => Task.CompletedTask,
+                rotateSession: () => { rotations++; config.SessionId = Guid.NewGuid().ToString(); return config.SessionId; },
+                rotateOnSessionGone: true);
+
+            Assert.Equal(SessionRegistrationOutcome.SessionGone, result.Outcome);
+            Assert.Equal(2, apiClient.CallCount);
+            Assert.Equal(1, rotations);
+        }
+
+        [Fact]
+        public async Task Session_gone_with_a_failing_rotation_ends_the_run()
+        {
+            using var tmp = new TempDirectory();
+            var logger = NewLogger(tmp);
+            var config = NewConfig();
+
+            var apiClient = new FakeApiClient(_ => throw SessionGone());
+
+            var result = await SessionRegistrationHelper.RegisterWithRetryAsync(
+                apiClient, config, agentVersion: "0.0.0", logger: logger,
+                networkLinkWait: _ => Task.CompletedTask,
+                rotateSession: () => throw new IOException("disk full"),
+                rotateOnSessionGone: true);
+
+            Assert.Equal(SessionRegistrationOutcome.SessionGone, result.Outcome);
+            Assert.Equal(1, apiClient.CallCount);
+            Assert.Null(result.RotatedFromSessionId);
+        }
+
+        [Fact]
+        public async Task Session_gone_at_a_whiteglove_part2_start_without_rotation_hook_ends_the_run()
+        {
+            using var tmp = new TempDirectory();
+            var logger = NewLogger(tmp);
+            var config = NewConfig();
+
+            var apiClient = new FakeApiClient(_ => throw SessionGone());
+
+            var result = await SessionRegistrationHelper.RegisterWithRetryAsync(
+                apiClient, config, agentVersion: "0.0.0", logger: logger,
+                networkLinkWait: _ => Task.CompletedTask,
+                rotateOnSessionGone: true);
+
+            Assert.Equal(SessionRegistrationOutcome.SessionGone, result.Outcome);
+            Assert.Equal(1, apiClient.CallCount);
+        }
+
        [Fact]
        public async Task Fails_after_six_exceptions_without_auth_error()
        {
@@ -600,6 +600,111 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.SignalAdapters
            Assert.DoesNotContain(ingress.Posted, p => p.Kind == DecisionSignalKind.RealmJoinPackageCompleted);
        }

+        // ---- Detected carries the current phase (service-key attach) -------------------------
+
+        private sealed class PhaseHarness : IDisposable
+        {
+            private readonly TempDirectory _tmp = new TempDirectory();
+            public FakeSignalIngressSink Ingress { get; } = new FakeSignalIngressSink();
+            public int? Phase;
+            public RealmJoinWatcher Watcher { get; }
+            public RealmJoinWatcherAdapter Adapter { get; }
+
+            public PhaseHarness()
+            {
+                var registry = new FakeRealmJoinRegistry();
+                Watcher = new RealmJoinWatcher(
+                    new AgentLogger(_tmp.Path, AgentLogLevel.Info),
+                    enumeratePackageIds: registry.Enumerate,
+                    tryReadPackage: registry.TryRead,
+                    keyExists: registry.KeyExists,
+                    readVersionInfo: () => RealmJoinVersionInfo.Empty,
+                    readUninstallDisplayVersion: () => null,
+                    readDeploymentPhase: () => Phase);
+                Adapter = new RealmJoinWatcherAdapter(Watcher, Ingress, new VirtualClock(Fixed));
+            }
+
+            public string DetectedPhase() =>
+                Ingress.Posted.Single(p => p.Kind == DecisionSignalKind.RealmJoinDetected)
+                    .Payload![DecisionEngine.RealmJoinPayloadKeys.DeploymentPhase];
+
+            public void Dispose()
+            {
+                Adapter.Dispose();
+                Watcher.Dispose();
+                _tmp.Dispose();
+            }
+        }
+
+        [Theory]
+        [InlineData(101)]
+        [InlineData(200)]
+        public void Detected_carries_the_phase_RealmJoin_is_in_when_the_service_key_attaches(int phase)
+        {
+            // Agent restarted while RJ deploys. Detected used to say Blank, which reset the
+            // engine's persisted LastDeploymentPhase and hid from the keep-awake host that RJ had
+            // started — no PhaseChanged follows while the phase stays put.
+            using var h = new PhaseHarness { Phase = phase };
+
+            h.Watcher.TriggerServiceStageAttachedFromTest();
+
+            Assert.Equal(phase.ToString(), h.DetectedPhase());
+            Assert.True(h.Watcher.PackageWatchersArmedForTest);
+            Assert.DoesNotContain(h.Ingress.Posted, p => p.Kind == DecisionSignalKind.RealmJoinPhaseChanged);
+        }
+
+        [Fact]
+        public void Detected_with_a_completed_phase_resolves_in_the_same_pass()
+        {
+            using var h = new PhaseHarness { Phase = RealmJoinInfo.PhaseCompletedFirstDeployment };
+
+            h.Watcher.TriggerServiceStageAttachedFromTest();
+
+            Assert.Equal("110", h.DetectedPhase());
+            var kinds = h.Ingress.Posted
+                .Where(p => p.Kind == DecisionSignalKind.RealmJoinDetected || p.Kind == DecisionSignalKind.RealmJoinResolved)
+                .Select(p => p.Kind)
+                .ToList();
+            Assert.Equal(new[] { DecisionSignalKind.RealmJoinDetected, DecisionSignalKind.RealmJoinResolved }, kinds);
+        }
+
+        [Fact]
+        public void Phase_not_written_at_attach_reports_Blank_and_the_first_value_surfaces_as_PhaseChanged()
+        {
+            // Detected says Blank while Parameters\DeploymentPhase is missing; that report is the
+            // baseline, so a first value of 101 must not be swallowed silently.
+            using var h = new PhaseHarness { Phase = null };
+
+            h.Watcher.TriggerServiceStageAttachedFromTest();
+            Assert.Equal("0", h.DetectedPhase());
+            Assert.False(h.Watcher.PackageWatchersArmedForTest);
+
+            h.Phase = 101;
+            h.Watcher.TriggerCheckParametersFromTest();
+
+            var changed = Assert.Single(h.Ingress.Posted, p => p.Kind == DecisionSignalKind.RealmJoinPhaseChanged);
+            Assert.Equal("101", changed.Payload![DecisionEngine.RealmJoinPayloadKeys.DeploymentPhase]);
+            Assert.Equal("0", changed.Payload[DecisionEngine.RealmJoinPayloadKeys.PreviousPhase]);
+            Assert.True(h.Watcher.PackageWatchersArmedForTest);
+        }
+
+        [Fact]
+        public void Blank_at_attach_then_running_fires_one_PhaseChanged()
+        {
+            // The common first-run shape (RJ installed during the ESP, deployment starts after
+            // the user-ESP page closed): Blank on attach, 0 -> 101 later.
+            using var h = new PhaseHarness { Phase = 0 };
+
+            h.Watcher.TriggerServiceStageAttachedFromTest();
+            h.Watcher.TriggerCheckParametersFromTest();   // same value again — no change
+            h.Phase = 101;
+            h.Watcher.TriggerCheckParametersFromTest();
+
+            Assert.Equal("0", h.DetectedPhase());
+            var changed = Assert.Single(h.Ingress.Posted, p => p.Kind == DecisionSignalKind.RealmJoinPhaseChanged);
+            Assert.Equal("0", changed.Payload![DecisionEngine.RealmJoinPayloadKeys.PreviousPhase]);
+        }
+

        // ---- auto-update (Uninstall\RealmJoin) -----------------------------------------------

@@ -12,8 +12,8 @@ using Xunit;
 namespace AutopilotMonitor.Agent.V2.Core.Tests.Telemetry
 {
    /// <summary>
-    /// Regression coverage for the duplicate <c>performance_snapshot</c> events observed on
-    /// session c4c8d206-… (Bayer / Lenovo T14 Gen 5): two snapshots fired with timestamps
+    /// Regression coverage for duplicate <c>performance_snapshot</c> events observed in the
+    /// field (Lenovo T14 Gen 5): two snapshots fired with timestamps
    /// 0–1ms apart, the second one carrying a fresh-baseline net delta of 0. Root cause:
    /// <see cref="System.Threading.Timer"/> is documented to dispatch callbacks on different
    /// ThreadPool threads when a callback exceeds the period, and the
@@ -138,6 +138,37 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Transport
                () => client.GetDiagnosticsUploadUrlAsync("tenant-1", "session-1", "package.zip"));
        }

+        // ── 410: session gone, only when the backend said so ────────────────
+
+        [Fact]
+        public async Task Backend_410_on_registration_is_session_gone()
+        {
+            using var client = BuildClient(
+                HttpStatusCode.Gone,
+                "{\"success\":false,\"message\":\"Session is being deleted by an administrator (state=Tombstoned); registration is rejected.\"}",
+                "application/json");
+
+            var ex = await Assert.ThrowsAsync<BackendSessionGoneException>(
+                () => client.RegisterSessionAsync(new AutopilotMonitor.Shared.Models.SessionRegistration()));
+
+            Assert.Equal(410, ex.StatusCode);
+        }
+
+        [Fact]
+        public async Task A_410_without_the_backends_echo_stays_a_plain_http_error()
+        {
+            // Answered on the network path: the caller would end monitoring on a session-gone
+            // signal, so it must stay an ordinary, retried failure.
+            using var client = BuildClient(
+                HttpStatusCode.Gone,
+                "<html><head><title>Gone</title></head><body>Gone</body></html>",
+                "text/html",
+                fromBackend: false);
+
+            await Assert.ThrowsAsync<HttpRequestException>(
+                () => client.RegisterSessionAsync(new AutopilotMonitor.Shared.Models.SessionRegistration()));
+        }
+
        [Theory]
        [InlineData(null, null)]
        [InlineData("", null)]
@@ -6,6 +6,7 @@ using System.Threading;
 using System.Threading.Tasks;
 using AutopilotMonitor.Agent.V2.Core.Logging;
 using AutopilotMonitor.Agent.V2.Core.Tests.Harness;
+using AutopilotMonitor.Agent.V2.Core.Transport;
 using AutopilotMonitor.Agent.V2.Core.Transport.Telemetry;
 using Xunit;
 using AutopilotMonitor.Shared.Models;
@@ -35,6 +36,14 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Transport
                requiresImmediateFlush: false,
                enqueuedAtUtc: At);

+        private static ProxyObserver NewProxyObserver(AgentLogger logger) =>
+            new ProxyObserver(
+                () => new ProxySettings(false, null, null, null, null),
+                () => "direct",
+                logger,
+                new VirtualClock(At),
+                TimeSpan.FromSeconds(30));
+
        private static string ReadLogs(string path)
        {
            // AgentLogger writes to a dated file; scan the whole dir to stay robust to format.
@@ -235,5 +244,126 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Transport
            Assert.DoesNotContain("flushing", logContent);
            Assert.DoesNotContain("ingest", logContent);
        }
+
+        [Fact]
+        public async Task Network_failure_names_the_route_and_opens_a_series()
+        {
+            using var tmp = new TempDirectory();
+            var logger = new AgentLogger(tmp.Path, AgentLogLevel.Info);
+
+            var handler = new RecordingHttpMessageHandler();
+            handler.QueueThrow(new HttpRequestException("An error occurred while sending the request."));
+            using var http = new HttpClient(handler) { Timeout = TimeSpan.FromSeconds(30) };
+
+            var sut = new BackendTelemetryUploader(
+                httpClient: http, baseUrl: "https://backend.test", tenantId: "T1", logger: logger, proxy: NewProxyObserver(logger));
+
+            await sut.UploadBatchAsync(new[] { NewEventItem(1) }, CancellationToken.None);
+
+            var logContent = ReadLogs(tmp.Path);
+            Assert.Contains("ingest NETWORK fail after", logContent);
+            Assert.Contains("items=1, route=direct): ", logContent);
+            Assert.Contains("ProxyObserver: uploads are failing since", logContent);
+        }
+
+        [Fact]
+        public async Task Timeout_names_the_route_and_opens_a_series()
+        {
+            using var tmp = new TempDirectory();
+            var logger = new AgentLogger(tmp.Path, AgentLogLevel.Info);
+
+            var handler = new RecordingHttpMessageHandler();
+            handler.QueueThrow(new TaskCanceledException("A task was canceled."));
+            using var http = new HttpClient(handler) { Timeout = TimeSpan.FromSeconds(30) };
+
+            var sut = new BackendTelemetryUploader(
+                httpClient: http, baseUrl: "https://backend.test", tenantId: "T1", logger: logger, proxy: NewProxyObserver(logger));
+
+            await sut.UploadBatchAsync(new[] { NewEventItem(1) }, CancellationToken.None);
+
+            var logContent = ReadLogs(tmp.Path);
+            Assert.Contains("ingest TIMEOUT after", logContent);
+            Assert.Contains("items=1, route=direct): ", logContent);
+            Assert.Contains("ProxyObserver: uploads are failing since", logContent);
+        }
+
+        [Fact]
+        public async Task Interception_names_the_route_and_opens_a_series()
+        {
+            using var tmp = new TempDirectory();
+            var logger = new AgentLogger(tmp.Path, AgentLogLevel.Info);
+
+            var handler = new RecordingHttpMessageHandler();
+            handler.QueueForeign(HttpStatusCode.Forbidden, InterceptionFixtures.CertificateRequiredPage);
+            using var http = new HttpClient(handler) { Timeout = TimeSpan.FromSeconds(30) };
+
+            var sut = new BackendTelemetryUploader(
+                httpClient: http, baseUrl: "https://backend.test", tenantId: "T1", logger: logger, proxy: NewProxyObserver(logger));
+
+            var result = await sut.UploadBatchAsync(new[] { NewEventItem(1) }, CancellationToken.None);
+            Assert.True(result.IsIntercepted);
+
+            var logContent = ReadLogs(tmp.Path);
+            Assert.Contains(", route=direct).", logContent);
+            Assert.Contains("ProxyObserver: uploads are failing since", logContent);
+        }
+
+        [Fact]
+        public async Task A_successful_upload_ends_the_series()
+        {
+            using var tmp = new TempDirectory();
+            var logger = new AgentLogger(tmp.Path, AgentLogLevel.Info);
+
+            var handler = new RecordingHttpMessageHandler();
+            handler.QueueThrow(new HttpRequestException("An error occurred while sending the request."));
+            handler.QueueStatus(HttpStatusCode.OK);
+            using var http = new HttpClient(handler) { Timeout = TimeSpan.FromSeconds(30) };
+
+            var sut = new BackendTelemetryUploader(
+                httpClient: http, baseUrl: "https://backend.test", tenantId: "T1", logger: logger, proxy: NewProxyObserver(logger));
+
+            await sut.UploadBatchAsync(new[] { NewEventItem(1) }, CancellationToken.None);
+            await sut.UploadBatchAsync(new[] { NewEventItem(1) }, CancellationToken.None);
+
+            Assert.Contains("ProxyObserver: uploads work again after 1 failed attempt(s)", ReadLogs(tmp.Path));
+        }
+
+        [Fact]
+        public async Task An_answer_from_the_backend_that_is_not_a_success_leaves_the_series_alone()
+        {
+            using var tmp = new TempDirectory();
+            var logger = new AgentLogger(tmp.Path, AgentLogLevel.Info);
+
+            var handler = new RecordingHttpMessageHandler();
+            handler.QueueStatus(HttpStatusCode.InternalServerError);
+            using var http = new HttpClient(handler) { Timeout = TimeSpan.FromSeconds(30) };
+
+            var sut = new BackendTelemetryUploader(
+                httpClient: http, baseUrl: "https://backend.test", tenantId: "T1", logger: logger, proxy: NewProxyObserver(logger));
+
+            await sut.UploadBatchAsync(new[] { NewEventItem(1) }, CancellationToken.None);
+
+            Assert.DoesNotContain("ProxyObserver: uploads", ReadLogs(tmp.Path));
+        }
+
+        [Fact]
+        public async Task Without_an_observer_the_failure_line_stays_as_it_was()
+        {
+            using var tmp = new TempDirectory();
+            var logger = new AgentLogger(tmp.Path, AgentLogLevel.Info);
+
+            var handler = new RecordingHttpMessageHandler();
+            handler.QueueThrow(new HttpRequestException("An error occurred while sending the request."));
+            using var http = new HttpClient(handler) { Timeout = TimeSpan.FromSeconds(30) };
+
+            var sut = new BackendTelemetryUploader(
+                httpClient: http, baseUrl: "https://backend.test", tenantId: "T1", logger: logger);
+
+            await sut.UploadBatchAsync(new[] { NewEventItem(1) }, CancellationToken.None);
+
+            var logContent = ReadLogs(tmp.Path);
+            Assert.Contains("items=1): ", logContent);
+            Assert.DoesNotContain("route=", logContent);
+        }
    }
 }
@@ -550,6 +550,24 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Transport
            Assert.Contains("network", result.ErrorReason);
        }

+        [Fact]
+        public async Task Network_error_reason_names_the_cause_instead_of_the_generic_text()
+        {
+            using var rig = new Rig();
+            rig.Handler.QueueThrow(new HttpRequestException(
+                "An error occurred while sending the request.",
+                new WebException(
+                    "Unable to connect to the remote server",
+                    new System.Net.Sockets.SocketException((int)System.Net.Sockets.SocketError.TimedOut),
+                    WebExceptionStatus.ConnectFailure,
+                    null)));
+
+            var result = await rig.Sut.UploadBatchAsync(new[] { NewEventItem(1) }, CancellationToken.None);
+
+            Assert.True(result.IsTransient);
+            Assert.StartsWith("network: status=ConnectFailure, socket=TimedOut: ", result.ErrorReason);
+        }
+
        [Fact]
        public async Task HttpClient_timeout_maps_to_Transient()
        {
@@ -0,0 +1,366 @@
+using System;
+using System.Collections.Generic;
+using System.IO;
+using System.Linq;
+using System.Threading;
+using AutopilotMonitor.Agent.V2.Core.Logging;
+using AutopilotMonitor.Agent.V2.Core.Tests.Harness;
+using AutopilotMonitor.Agent.V2.Core.Transport;
+using Xunit;
+
+namespace AutopilotMonitor.Agent.V2.Core.Tests.Transport
+{
+    /// <summary>Settings and route are played in: no test changes a real proxy setting.</summary>
+    public sealed class ProxyObserverTests : IDisposable
+    {
+        private static readonly ProxySettings AutoDetect = new ProxySettings(true, null, null, null, null);
+        private static readonly ProxySettings NoProxy = new ProxySettings(false, null, null, null, null);
+
+        private readonly TempDirectory _tmp = new TempDirectory();
+        private readonly VirtualClock _clock = new VirtualClock(new DateTime(2026, 11, 2, 6, 29, 13, DateTimeKind.Utc));
+        private ProxySettings _settings = AutoDetect;
+        private string _route = "proxy.example.test:8080";
+
+        private ProxyObserver NewObserver(Func<string>? readRoute = null, TimeSpan? routeBound = null, Func<ProxySettings>? readSettings = null) =>
+            new ProxyObserver(
+                readSettings ?? (() => _settings),
+                readRoute ?? (() => _route),
+                new AgentLogger(_tmp.Path, AgentLogLevel.Info),
+                _clock,
+                routeBound ?? TimeSpan.FromSeconds(30));
+
+        private ProxyObserver StartedObserver()
+        {
+            var observer = NewObserver();
+            observer.CaptureBaseline();
+            return observer;
+        }
+
+        private void SwitchToNoProxy()
+        {
+            _settings = NoProxy;
+            _route = "direct";
+        }
+
+        private List<string> LogLines()
+        {
+            var lines = new List<string>();
+            foreach (var file in Directory.EnumerateFiles(_tmp.Path, "*.log", SearchOption.AllDirectories))
+            {
+                using var stream = new FileStream(file, FileMode.Open, FileAccess.Read, FileShare.ReadWrite);
+                using var reader = new StreamReader(stream);
+                lines.AddRange(reader.ReadToEnd().Split(new[] { '\r', '\n' }, StringSplitOptions.RemoveEmptyEntries));
+            }
+            return lines.Where(l => l.Contains("ProxyObserver:")).ToList();
+        }
+
+        public void Dispose() => _tmp.Dispose();
+
+        [Fact]
+        public void The_baseline_names_settings_and_route_at_info()
+        {
+            StartedObserver();
+
+            var line = Assert.Single(LogLines());
+            Assert.Contains("[INFO]", line);
+            Assert.Contains("start - IE settings of this account: auto-detect; WinHTTP: direct; route to backend: proxy.example.test:8080", line);
+        }
+
+        [Fact]
+        public void A_rebuild_of_the_clients_does_not_repeat_the_baseline()
+        {
+            var logger = new AgentLogger(_tmp.Path, AgentLogLevel.Info);
+            foreach (var _ in new[] { 1, 2 })
+            {
+                new ProxyObserver(() => _settings, () => _route, logger, _clock, TimeSpan.FromSeconds(30)).CaptureBaseline();
+            }
+
+            Assert.Single(LogLines());
+        }
+
+        [Fact]
+        public void A_change_warns_once_with_both_sides()
+        {
+            var observer = StartedObserver();
+            SwitchToNoProxy();
+
+            observer.CheckForChange();
+            observer.CheckForChange();
+
+            var line = Assert.Single(LogLines().Skip(1));
+            Assert.Contains("[WARN]", line);
+            Assert.Contains("proxy settings changed - IE settings of this account: auto-detect -> no proxy; route to backend: proxy.example.test:8080 -> direct.", line);
+            Assert.Contains("bitsadmin /util /getieproxy localsystem", line);
+        }
+
+        [Fact]
+        public void Rewriting_the_same_content_says_nothing()
+        {
+            var observer = StartedObserver();
+            _settings = new ProxySettings(true, null, null, null, null);
+
+            observer.CheckForChange();
+
+            Assert.Single(LogLines());
+        }
+
+        [Fact]
+        public void A_winhttp_change_says_uploads_do_not_use_it()
+        {
+            var observer = StartedObserver();
+            _settings = new ProxySettings(true, null, null, null, "p:8080");
+
+            observer.CheckForChange();
+
+            var line = LogLines().Last();
+            Assert.Contains("[WARN]", line);
+            Assert.Contains("WinHTTP: direct -> proxy p:8080", line);
+            Assert.Contains("do not use WinHTTP", line);
+        }
+
+        [Fact]
+        public void A_winhttp_change_is_not_blamed_for_failing_uploads()
+        {
+            var observer = StartedObserver();
+            _settings = new ProxySettings(true, null, null, null, "p:8080");
+            observer.CheckForChange();
+
+            observer.OnSendFailed(TimeSpan.Zero);
+
+            Assert.Contains("Proxy settings of this account unchanged since start: auto-detect.", LogLines().Last());
+        }
+
+        [Fact]
+        public void A_change_reaches_the_subscriber_with_settings_and_route()
+        {
+            var observer = StartedObserver();
+            ProxySettings? seen = null;
+            string? seenWhat = null;
+            string? seenRoute = null;
+            observer.SettingsChanged += (settings, what, route) =>
+            {
+                seen = settings;
+                seenWhat = what;
+                seenRoute = route;
+            };
+            SwitchToNoProxy();
+
+            observer.CheckForChange();
+
+            Assert.Equal(NoProxy, seen);
+            Assert.Equal("IE settings of this account: auto-detect -> no proxy", seenWhat);
+            Assert.Equal("direct", seenRoute);
+        }
+
+        [Fact]
+        public void A_subscriber_that_throws_does_not_reach_the_caller()
+        {
+            var observer = StartedObserver();
+            observer.SettingsChanged += (_, _, _) => throw new InvalidOperationException("SignalIngress has been stopped.");
+            SwitchToNoProxy();
+
+            observer.CheckForChange();
+
+            Assert.Contains(LogLines(), l => l.Contains("proxy settings changed"));
+        }
+
+        [Fact]
+        public void The_first_failure_ties_the_series_to_the_change()
+        {
+            var observer = StartedObserver();
+            _clock.Advance(TimeSpan.FromMinutes(23));
+            observer.OnSendSucceeded();
+            _clock.Advance(TimeSpan.FromSeconds(90));
+            SwitchToNoProxy();
+            observer.CheckForChange();
+            _clock.Advance(TimeSpan.FromSeconds(62));
+
+            observer.OnSendFailed(TimeSpan.FromSeconds(21));
+
+            var line = LogLines().Last();
+            Assert.Contains("[WARN]", line);
+            Assert.Contains("uploads are failing since 06:54:24, 41 s after the proxy settings changed at 06:53:43 (IE settings of this account: auto-detect -> no proxy).", line);
+            Assert.Contains("Route to backend: direct. Last successful upload 06:52:13.", line);
+        }
+
+        [Fact]
+        public void A_failure_notices_a_change_the_watcher_did_not_report()
+        {
+            var observer = StartedObserver();
+            SwitchToNoProxy();
+
+            observer.OnSendFailed(TimeSpan.Zero);
+
+            var lines = LogLines();
+            Assert.Contains(lines, l => l.Contains("proxy settings changed - IE settings of this account: auto-detect -> no proxy"));
+            Assert.Contains("after the proxy settings changed", lines.Last());
+        }
+
+        [Fact]
+        public void A_series_writes_its_finding_once()
+        {
+            var observer = StartedObserver();
+
+            observer.OnSendFailed(TimeSpan.Zero);
+            observer.OnSendFailed(TimeSpan.Zero);
+            observer.OnSendFailed(TimeSpan.Zero);
+
+            Assert.Single(LogLines(), l => l.Contains("uploads are failing"));
+        }
+
+        [Fact]
+        public void A_failure_without_a_change_says_the_settings_are_unchanged()
+        {
+            var observer = StartedObserver();
+
+            observer.OnSendFailed(TimeSpan.Zero);
+
+            var line = LogLines().Last();
+            Assert.Contains("Proxy settings of this account unchanged since start: auto-detect.", line);
+            Assert.Contains("Route to backend: proxy.example.test:8080. No successful upload yet.", line);
+        }
+
+        [Fact]
+        public void A_change_before_the_last_success_is_not_blamed()
+        {
+            var observer = StartedObserver();
+            SwitchToNoProxy();
+            observer.CheckForChange();
+            _clock.Advance(TimeSpan.FromMinutes(1));
+            observer.OnSendSucceeded();
+            _clock.Advance(TimeSpan.FromMinutes(1));
+
+            observer.OnSendFailed(TimeSpan.Zero);
+
+            Assert.Contains("Proxy settings of this account unchanged since the last successful upload: no proxy.", LogLines().Last());
+        }
+
+        [Fact]
+        public void Recovery_is_noted_and_a_new_series_gets_its_own_finding()
+        {
+            var observer = StartedObserver();
+            observer.OnSendFailed(TimeSpan.Zero);
+            observer.OnSendFailed(TimeSpan.Zero);
+            _clock.Advance(TimeSpan.FromMinutes(9));
+
+            observer.OnSendSucceeded();
+
+            var line = LogLines().Last();
+            Assert.Contains("[INFO]", line);
+            Assert.Contains("uploads work again after 2 failed attempt(s) over 9 min; route to backend: proxy.example.test:8080.", line);
+
+            observer.OnSendFailed(TimeSpan.Zero);
+            Assert.Equal(2, LogLines().Count(l => l.Contains("uploads are failing")));
+        }
+
+        [Fact]
+        public void Recovery_reports_settings_that_came_back()
+        {
+            var observer = StartedObserver();
+            SwitchToNoProxy();
+            observer.OnSendFailed(TimeSpan.Zero);
+            _settings = AutoDetect;
+            _route = "proxy.example.test:8080";
+
+            observer.OnSendSucceeded();
+
+            Assert.Contains(LogLines(), l => l.Contains("no proxy -> auto-detect"));
+        }
+
+        [Fact]
+        public void A_success_without_a_series_stays_silent()
+        {
+            var observer = StartedObserver();
+
+            observer.OnSendSucceeded();
+
+            Assert.Single(LogLines());
+        }
+
+        [Fact]
+        public void Stopping_while_failing_sums_it_up()
+        {
+            var observer = StartedObserver();
+            observer.OnSendSucceeded();
+            _clock.Advance(TimeSpan.FromMinutes(1));
+            SwitchToNoProxy();
+            observer.OnSendFailed(TimeSpan.Zero);
+            observer.OnSendFailed(TimeSpan.Zero);
+
+            observer.LogOpenFailures();
+
+            var line = LogLines().Last();
+            Assert.Contains("[WARN]", line);
+            Assert.Contains("stopping with uploads still failing: 2 failed attempt(s) since 06:30:13, last success 06:29:13, route to backend: direct.", line);
+            Assert.Contains("Proxy settings changed at 06:30:13 (IE settings of this account: auto-detect -> no proxy).", line);
+        }
+
+        [Fact]
+        public void Stopping_without_a_series_stays_silent()
+        {
+            var observer = StartedObserver();
+            observer.OnSendFailed(TimeSpan.Zero);
+            observer.OnSendSucceeded();
+            var before = LogLines().Count;
+
+            observer.LogOpenFailures();
+
+            Assert.Equal(before, LogLines().Count);
+        }
+
+        [Fact]
+        public void A_settings_read_that_throws_is_not_a_change_and_never_reaches_the_upload()
+        {
+            var throwing = false;
+            var observer = NewObserver(readSettings: () => throwing ? throw new InvalidOperationException("boom") : _settings);
+            observer.CaptureBaseline();
+            throwing = true;
+
+            observer.CheckForChange();
+            observer.OnSendFailed(TimeSpan.Zero);
+
+            Assert.DoesNotContain(LogLines(), l => l.Contains("proxy settings changed"));
+            Assert.Contains("Proxy settings of this account unchanged since start: auto-detect.", LogLines().Last());
+        }
+
+        [Fact]
+        public void An_unreadable_state_is_not_a_change()
+        {
+            var observer = StartedObserver();
+            _settings = ProxySettings.Unreadable(5);
+
+            observer.CheckForChange();
+
+            Assert.Single(LogLines());
+        }
+
+        [Fact]
+        public void A_route_read_that_throws_reads_as_unknown()
+        {
+            var observer = NewObserver(readRoute: () => throw new InvalidOperationException("boom"));
+
+            Assert.Equal("unknown", observer.RouteText());
+        }
+
+        [Fact]
+        public void A_hanging_route_read_gives_up_and_does_not_pile_up()
+        {
+            using var release = new ManualResetEventSlim(false);
+            var reads = 0;
+            var observer = NewObserver(
+                readRoute: () =>
+                {
+                    Interlocked.Increment(ref reads);
+                    release.Wait();
+                    return "direct";
+                },
+                routeBound: TimeSpan.FromMilliseconds(50));
+
+            Assert.Equal("unknown", observer.RouteText());
+            Assert.Equal("unknown", observer.RouteText());
+            Assert.Equal(1, Volatile.Read(ref reads));
+
+            release.Set();
+        }
+    }
+}
@@ -0,0 +1,167 @@
+using System;
+using System.Threading.Tasks;
+using AutopilotMonitor.Agent.V2.Core.Transport;
+using Xunit;
+
+namespace AutopilotMonitor.Agent.V2.Core.Tests.Transport
+{
+    public sealed class ProxySettingsTests
+    {
+        private static ProxySettings Settings(
+            bool autoDetect = false, string? pac = null, string? proxy = null, string? bypass = null, string? winHttp = null) =>
+            new ProxySettings(autoDetect, pac, proxy, bypass, winHttp);
+
+        [Fact]
+        public void Each_kind_of_setting_describes_itself()
+        {
+            Assert.Equal("no proxy", Settings().Describe());
+            Assert.Equal("auto-detect", Settings(autoDetect: true).Describe());
+            Assert.Equal("PAC https://pac.example.test/proxy.pac", Settings(pac: "https://pac.example.test/proxy.pac").Describe());
+            Assert.Equal("proxy proxy.example.test:8080", Settings(proxy: "proxy.example.test:8080").Describe());
+            Assert.Equal("auto-detect, proxy p:8080", Settings(autoDetect: true, proxy: "p:8080").Describe());
+            Assert.Equal("direct", Settings().DescribeWinHttp());
+            Assert.Equal("proxy p:8080", Settings(winHttp: "p:8080").DescribeWinHttp());
+            Assert.Equal("unreadable (Win32 error 5)", ProxySettings.Unreadable(5).Describe());
+        }
+
+        [Theory]
+        [InlineData(false, null, null, "Direct")]
+        [InlineData(true, null, null, "AutoDetect")]
+        [InlineData(true, "https://pac.example.test/p.pac", null, "PAC")]
+        [InlineData(true, "https://pac.example.test/p.pac", "p:8080", "Proxy")]
+        public void Type_keeps_the_values_the_download_rule_matches(bool autoDetect, string? pac, string? proxy, string expected)
+        {
+            Assert.Equal(expected, Settings(autoDetect, pac, proxy).ProxyType);
+        }
+
+        [Fact]
+        public void An_unreadable_state_has_its_own_type()
+        {
+            Assert.Equal("Unknown", ProxySettings.Unreadable(5).ProxyType);
+        }
+
+        [Fact]
+        public void Equal_content_is_equal_and_any_field_makes_it_different()
+        {
+            Assert.Equal(Settings(autoDetect: true), Settings(autoDetect: true));
+            Assert.NotEqual(Settings(autoDetect: true), Settings());
+            Assert.NotEqual(Settings(pac: "https://a.test/p"), Settings(pac: "https://b.test/p"));
+            Assert.NotEqual(Settings(proxy: "a:1"), Settings(proxy: "b:1"));
+            Assert.NotEqual(Settings(proxy: "a:1", bypass: "x"), Settings(proxy: "a:1", bypass: "y"));
+            Assert.NotEqual(Settings(winHttp: "a:1"), Settings());
+        }
+
+        [Fact]
+        public void An_empty_string_counts_as_not_set()
+        {
+            Assert.Equal(Settings(), Settings(pac: "", proxy: "", bypass: "", winHttp: ""));
+        }
+
+        [Theory]
+        [InlineData("user:secret@p:8080")]
+        [InlineData("http://user:secret@p:8080")]
+        [InlineData("http=user:secret@p:8080;https=user:secret@q:8443")]
+        [InlineData("user:se=cret@p:8080")]
+        [InlineData("user:se;cret@p:8080")]
+        [InlineData("http=user:se;cret@p:8080")]
+        [InlineData("user:se://cret@p:8080")]
+        public void Credentials_never_reach_logs_or_events(string configured)
+        {
+            var settings = Settings(proxy: configured, winHttp: configured);
+            var data = settings.ToEventData();
+
+            foreach (var text in new[] { settings.DescribeAll(), (string)data["proxyServer"], (string)data["winHttpProxy"] })
+            {
+                Assert.DoesNotContain("user", text);
+                Assert.DoesNotContain("cret", text);
+            }
+
+            Assert.Equal(ProxySettings.CredentialsHidden, settings.Proxy);
+            Assert.Equal(ProxySettings.CredentialsHidden, settings.WinHttpProxy);
+            Assert.True((bool)data["proxyEnabled"]);
+            Assert.True((bool)data["winHttpProxyConfigured"]);
+        }
+
+        [Theory]
+        [InlineData("p:8080")]
+        [InlineData("http://p:8080")]
+        [InlineData("http=p:8080;https=q:8443")]
+        public void A_value_without_credentials_stays_as_it_is(string configured)
+        {
+            Assert.Equal(configured, Settings(proxy: configured).Proxy);
+            Assert.Equal(configured, Settings(winHttp: configured).WinHttpProxy);
+        }
+
+        [Theory]
+        [InlineData("https://pac.example.test/p.pac?key=secret", "https://pac.example.test/p.pac")]
+        [InlineData("http://user:secret@pac.example.test:8080/p.pac", "http://pac.example.test:8080/p.pac")]
+        [InlineData("http://user:se=cr;et@pac.example.test/p.pac", "http://pac.example.test/p.pac")]
+        [InlineData("not a url with secret", "(unparsable URL)")]
+        public void A_pac_url_keeps_scheme_host_port_and_path(string configured, string expected)
+        {
+            Assert.Equal(expected, Settings(pac: configured).PacUrl);
+        }
+
+        [Fact]
+        public void A_change_names_what_moved()
+        {
+            var before = Settings(autoDetect: true);
+
+            Assert.Equal("IE settings of this account: auto-detect -> no proxy", Settings().DescribeChangeFrom(before));
+            Assert.Equal("WinHTTP: direct -> proxy p:1", Settings(autoDetect: true, winHttp: "p:1").DescribeChangeFrom(before));
+            Assert.Equal(
+                "IE settings of this account: auto-detect -> no proxy; WinHTTP: direct -> proxy p:1",
+                Settings(winHttp: "p:1").DescribeChangeFrom(before));
+            Assert.Equal(
+                "IE settings of this account: proxy bypass list changed",
+                Settings(proxy: "p:1", bypass: "b").DescribeChangeFrom(Settings(proxy: "p:1", bypass: "a")));
+        }
+
+        [Fact]
+        public void Only_the_account_settings_count_as_a_change_for_uploads()
+        {
+            var before = Settings(autoDetect: true);
+
+            Assert.True(Settings().DiffersForUploadsFrom(before));
+            Assert.False(Settings(autoDetect: true, winHttp: "p:1").DiffersForUploadsFrom(before));
+        }
+
+        [Fact]
+        public void The_event_tells_auto_detect_from_direct()
+        {
+            var data = Settings(autoDetect: true).ToEventData();
+
+            Assert.Equal("AutoDetect", data["proxyType"]);
+            Assert.True((bool)data["autoDetect"]);
+            Assert.False((bool)data["proxyEnabled"]);
+            Assert.Null(data["proxyServer"]);
+            Assert.False((bool)data["winHttpProxyConfigured"]);
+            Assert.Null(data["winHttpProxy"]);
+        }
+
+        [Fact]
+        public void The_event_carries_a_real_winhttp_proxy()
+        {
+            var data = Settings(winHttp: "p:8080").ToEventData();
+
+            Assert.True((bool)data["winHttpProxyConfigured"]);
+            Assert.Equal("p:8080", data["winHttpProxy"]);
+        }
+
+        [Fact]
+        public void The_real_settings_of_this_account_can_be_read()
+        {
+            var settings = ProxySettingsReader.Read();
+
+            Assert.False(settings.IsUnreadable, settings.Describe());
+        }
+
+        [Fact]
+        public async Task The_real_route_can_be_read()
+        {
+            var read = Task.Run(() => ProxySettingsReader.ReadRoute(new Uri("https://backend.example.invalid/")));
+
+            Assert.False(string.IsNullOrEmpty(await read));
+        }
+    }
+}
@@ -2,7 +2,9 @@ using System;
 using System.ComponentModel;
 using System.Net;
 using System.Net.Http;
+using System.Net.Sockets;
 using System.Security.Authentication;
+using System.Threading.Tasks;
 using AutopilotMonitor.Agent.V2.Core.Monitoring.Transport;
 using Xunit;

@@ -69,5 +71,56 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Transport
            Assert.Equal("boom", TransportErrorCodes.MessageWithNativeCode(new InvalidOperationException("boom")));
            Assert.Null(TransportErrorCodes.MessageWithNativeCode(null!));
        }
+
+        // The .NET Framework shape of a failed connect or name lookup through HttpClient.
+        private static Exception SendFailureChain(WebExceptionStatus status, SocketError socketError) =>
+            new HttpRequestException(
+                "An error occurred while sending the request.",
+                new WebException("Unable to connect to the remote server", new SocketException((int)socketError), status, null));
+
+        [Theory]
+        [InlineData(WebExceptionStatus.ConnectFailure, SocketError.TimedOut, "status=ConnectFailure, socket=TimedOut: ")]
+        [InlineData(WebExceptionStatus.NameResolutionFailure, SocketError.HostNotFound, "status=NameResolutionFailure, socket=HostNotFound: ")]
+        public void Send_failure_names_status_and_socket_error(WebExceptionStatus status, SocketError socketError, string expectedPrefix)
+        {
+            var described = TransportErrorCodes.DescribeSendFailure(SendFailureChain(status, socketError));
+
+            Assert.StartsWith(expectedPrefix, described);
+            Assert.DoesNotContain("An error occurred while sending the request", described);
+        }
+
+        [Fact]
+        public void Send_failure_of_a_tls_handshake_names_status_and_native_code()
+        {
+            var described = TransportErrorCodes.DescribeSendFailure(TlsFailureChain(new Win32Exception(IllegalMessage)));
+
+            Assert.StartsWith("status=SecureChannelFailure, win32=0x80090326: ", described);
+        }
+
+        [Fact]
+        public void Send_failure_without_details_is_the_innermost_message()
+        {
+            Assert.Equal("inner", TransportErrorCodes.DescribeSendFailure(new HttpRequestException("outer", new InvalidOperationException("inner"))));
+            Assert.Equal("boom", TransportErrorCodes.DescribeSendFailure(new InvalidOperationException("boom")));
+            Assert.Null(TransportErrorCodes.DescribeSendFailure(null!));
+        }
+
+        [Fact]
+        public async Task Real_refused_connect_names_the_endpoint_it_tried()
+        {
+            // The endpoint in the message is what tells the backend from a proxy, and only a real
+            // connect produces it: a hand-built SocketException carries none.
+            var listener = new TcpListener(IPAddress.Loopback, 0);
+            listener.Start();
+            var port = ((IPEndPoint)listener.LocalEndpoint).Port;
+            listener.Stop();
+
+            using var client = new HttpClient(new HttpClientHandler { UseProxy = false });
+            var failure = await Assert.ThrowsAsync<HttpRequestException>(() => client.GetAsync($"http://127.0.0.1:{port}/"));
+
+            var described = TransportErrorCodes.DescribeSendFailure(failure);
+            Assert.StartsWith("status=ConnectFailure, socket=ConnectionRefused: ", described);
+            Assert.Contains($"127.0.0.1:{port}", described);
+        }
    }
 }
@@ -44,7 +44,7 @@
  <Import Project="V2Isolation.targets" />

  <ItemGroup>
-    <PackageReference Include="Newtonsoft.Json" Version="13.0.3" />
+    <PackageReference Include="Newtonsoft.Json" Version="13.0.4" />
  </ItemGroup>

  <ItemGroup>
@@ -0,0 +1,33 @@
+using System;
+using AutopilotMonitor.Agent.V2.Core.Monitoring.Interop;
+
+namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.Ime
+{
+    /// <summary>
+    /// Which file a path holds right now: volume serial plus file index. IME rolls a log with
+    /// <c>File.Move</c>, so the identity stays with the bytes when the name changes.
+    /// </summary>
+    internal static class ImeLogFileIdentity
+    {
+        /// <summary>
+        /// Null when the file cannot be opened. An attribute-only handle with full sharing, so it
+        /// can never make IME's rename of the log fail.
+        /// </summary>
+        public static string TryRead(string path)
+        {
+            using (var handle = FileNativeMethods.CreateFileW(
+                path,
+                FileNativeMethods.FILE_READ_ATTRIBUTES,
+                FileNativeMethods.FILE_SHARE_READ | FileNativeMethods.FILE_SHARE_WRITE | FileNativeMethods.FILE_SHARE_DELETE,
+                IntPtr.Zero,
+                FileNativeMethods.OPEN_EXISTING,
+                0,
+                IntPtr.Zero))
+            {
+                if (handle.IsInvalid) return null;
+                if (!FileNativeMethods.GetFileInformationByHandle(handle, out var info)) return null;
+                return $"{info.VolumeSerialNumber:X8}-{info.FileIndexHigh:X8}{info.FileIndexLow:X8}";
+            }
+        }
+    }
+}
@@ -1709,7 +1709,6 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.Ime
                {
                    _allAppsCompletedFired = true;
                    _logger.Info($"ImeLogTracker: all {_packageStates.CountAll} apps completed");
-                    OnAllAppsCompleted?.Invoke();
                }
            }
        }
@@ -51,23 +51,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.Ime
            if (!Directory.Exists(_logFolder))
                return;

-            // Get all matching log files, sorted by name (archived files come before current).
-            // M2: a SINGLE directory enumeration filtered in-memory against the patterns, instead
-            // of one Directory.GetFiles(pattern) per LogFilePattern every 100 ms poll (~90 folder
-            // enumerations/s → 1). The in-memory regex match is anchored, so it is also immune to
-            // the Win32 "*.ext" 8.3 search-pattern quirk.
-            var files = new List<string>();
-            try
-            {
-                foreach (var filePath in Directory.EnumerateFiles(_logFolder))
-                {
-                    if (MatchesLogFilePattern(Path.GetFileName(filePath)))
-                        files.Add(filePath);
-                }
-            }
-            catch (DirectoryNotFoundException) { }
-
-            files.Sort(StringComparer.OrdinalIgnoreCase);
+            var files = EnumerateLogFiles();
+            if (FileIdentitiesAreDue(files)) ReconcileFileIdentities(files);

            // Σ(file length − bookmark) after this pass — the tracker's queue depth.
            long backlogBytes = 0;
@@ -94,6 +79,66 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.Ime
            }
        }

+        /// <summary>
+        /// All matching log files, sorted by name (archived files come before current).
+        /// M2: a SINGLE directory enumeration filtered in-memory against the patterns, instead
+        /// of one Directory.GetFiles(pattern) per LogFilePattern every 100 ms poll (~90 folder
+        /// enumerations/s → 1). The in-memory regex match is anchored, so it is also immune to
+        /// the Win32 "*.ext" 8.3 search-pattern quirk.
+        /// </summary>
+        private List<string> EnumerateLogFiles()
+        {
+            var files = new List<string>();
+            try
+            {
+                foreach (var filePath in Directory.EnumerateFiles(_logFolder))
+                {
+                    if (MatchesLogFilePattern(Path.GetFileName(filePath)))
+                        files.Add(filePath);
+                }
+            }
+            catch (DirectoryNotFoundException) { }
+
+            files.Sort(StringComparer.OrdinalIgnoreCase);
+            return files;
+        }
+
+        /// <summary>
+        /// On the first pass (a restart can have rolled logs over) and when a file has no known
+        /// identity yet, which is how a rolled-over archive first shows up. Nothing is opened in
+        /// the regular poll.
+        /// </summary>
+        private bool FileIdentitiesAreDue(List<string> files)
+        {
+            if (!_fileIdentitiesReconciled) return true;
+            foreach (var filePath in files)
+            {
+                if (!_positionTracker.HasIdentity(filePath)) return true;
+            }
+            return false;
+        }
+
+        /// <summary>
+        /// Lets every bookmark follow its file (see <see cref="LogFilePositionTracker.Reconcile"/>).
+        /// Reading a rolled-over log again would replay every app and script line in it: finished
+        /// apps fall back to Installing, and the subgraph line of an older app marks the app that is
+        /// running right now as skipped.
+        /// </summary>
+        private void ReconcileFileIdentities(List<string> files)
+        {
+            _fileIdentitiesReconciled = true;
+
+            var idByPath = new Dictionary<string, string>(StringComparer.OrdinalIgnoreCase);
+            foreach (var filePath in files) idByPath[filePath] = FileIdentityProvider(filePath);
+
+            foreach (var move in _positionTracker.Reconcile(idByPath))
+            {
+                MoveFileContext(move.From, move.To);
+                _logger.Info($"ImeLogTracker: {Path.GetFileName(move.From)} rolled over to {Path.GetFileName(move.To)} - continuing at offset {move.Position} instead of reading it again");
+            }
+            _stateDirty = true;
+        }
+
        /// <summary>
        /// One pass over one file: the bytes behind the bookmark, on a multi-writer file preceded
        /// by the overwrite check that may move the bookmark back first (see
@@ -104,6 +149,12 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.Ime
            var fileInfo = new FileInfo(filePath);
            if (!fileInfo.Exists) return 0;

+            // IME renamed the file after this pass listed the folder, or its archive sorts behind it
+            // (_IntuneManagementExtension.log). Either way the archive needs the bookmark before the
+            // read below resets it.
+            if (_positionTracker.IsBehindBookmark(filePath, fileInfo.Length))
+                ReconcileFileIdentities(EnumerateLogFiles());
+
            // Captured BEFORE MarkChecked below stamps this pass. Growth measured
            // against a previously observed state is what makes this pass's lines valid
            // "written now" anchors — for the per-file measurement AND per-line anchoring.
@@ -616,6 +616,35 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.Ime

        private void InvalidateInvocationMarkersFrom(string fileName, long offset) => TakeInvocationMarkersFrom(fileName, offset, out _);

+        /// <summary>
+        /// A log was rolled over: what the tracker knows about its bytes goes with them. The markers keep
+        /// <see cref="_lastPlatformMarker"/> alive, so the run in flight still owns its lines in the fresh file;
+        /// the ledger stays behind and empties, an archive is not checked for overwrites.
+        /// </summary>
+        private void MoveFileContext(string fromPath, string toPath)
+        {
+            var from = Path.GetFileName(fromPath);
+            var to = Path.GetFileName(toPath);
+
+            List<InvocationMarker> markers;
+            if (_invocationMarkers.TryGetValue(from, out markers))
+            {
+                _invocationMarkers.Remove(from);
+                _invocationMarkers[to] = markers;
+            }
+            if (_platformMarkerFiles.Contains(from)) _platformMarkerFiles.Add(to);
+
+            FileLedger ledger;
+            if (_ledgers.TryGetValue(from, out ledger)) ledger.Clear();
+
+            HeldTail held;
+            if (_heldTails.TryGetValue(fromPath, out held))
+            {
+                _heldTails.Remove(fromPath);
+                _heldTails[toPath] = held;
+            }
+        }
+
        /// <summary>
        /// An entry that reads unchanged after a rewind keeps its markers: gives back the set-aside markers at exactly
        /// <paramref name="entryOffset"/>. Set-aside markers in front of it belonged to entries that changed and stay
@@ -88,6 +88,12 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.Ime
        // system clock, ImeLogHost rewires it to the agent IClock, tests to their VirtualClock.
        internal Func<DateTime> UtcNowProvider { get; set; } = () => DateTime.UtcNow;

+        // Which file a path holds; null when unreadable. Tests swap it to cover that path.
+        internal Func<string, string> FileIdentityProvider { get; set; } = ImeLogFileIdentity.TryRead;
+
+        // False until the bookmarks were checked against the disk once in this process.
+        private bool _fileIdentitiesReconciled;
+
        /// <summary>
        /// CMTrace timestamps from IME are emitted in UTC, but DateTimeKind may arrive as
        /// Unspecified depending on the parser path. Normalize via SpecifyKind=Utc rather than
@@ -494,7 +500,6 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.Ime
        public Action OnImeStarted { get; set; }
        public Action<AppPackageState, AppInstallationState, AppInstallationState> OnAppStateChanged { get; set; }
        public Action<string> OnPoliciesDiscovered { get; set; }
-        public Action OnAllAppsCompleted { get; set; }
        public Action OnUserSessionCompleted { get; set; }
        public Action<string> OnImeSessionChange { get; set; }
        // Args: errorCode (may be empty when IME logged none), raw failure line excerpt.
@@ -954,13 +959,10 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.Ime
            {
                if (!Directory.Exists(_logFolder)) return;
                var inputs = new List<ImeLogEraPreScan.ScanInput>();
-                var files = new List<string>();
-                foreach (var filePath in Directory.EnumerateFiles(_logFolder))
-                {
-                    if (MatchesLogFilePattern(Path.GetFileName(filePath)))
-                        files.Add(filePath);
-                }
-                files.Sort(StringComparer.OrdinalIgnoreCase);
+                var files = EnumerateLogFiles();
+                // First: the read below resets the bookmark of a file that shrank, and the archive
+                // that file moved to during the downtime still needs that bookmark.
+                ReconcileFileIdentities(files);
                foreach (var filePath in files)
                {
                    var info = new FileInfo(filePath);
@@ -994,9 +996,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.Ime
            LoadState();

            // Era anchors for the backlog the first pass is about to read (2026-09-04). Runs
-            // before the poll loop so every replayed line already finds its era; read-only on
-            // the position tracker. Replay tooling anchors nothing — its logs did not come from
-            // this device's bootstrap.
+            // before the poll loop so every replayed line already finds its era. Replay tooling
+            // anchors nothing — its logs did not come from this device's bootstrap.
            if (!SimulationMode) PreScanEras();

            _cts = new CancellationTokenSource();
@@ -1180,6 +1181,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.Ime
                {
                    var fullPath = Path.Combine(_logFolder, kvp.Key);
                    _positionTracker.RestorePosition(fullPath, kvp.Value.Position, kvp.Value.LastKnownSize);
+                    _positionTracker.RestoreFileId(fullPath, kvp.Value.FileId);
                }
            }

@@ -1346,7 +1348,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.Ime
                state.FilePositions[fileName] = new FilePositionData
                {
                    Position = kvp.Value.Position,
-                    LastKnownSize = kvp.Value.LastKnownSize
+                    LastKnownSize = kvp.Value.LastKnownSize,
+                    FileId = _positionTracker.GetFileId(kvp.Key)
                };
            }

@@ -200,6 +200,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.Ime

        public void Dispose()
        {
+            Process attached;
            lock (_lock)
            {
                if (_disposed) return;
@@ -208,12 +209,16 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.Ime
                _discoveryTimer?.Dispose();
                _discoveryTimer = null;

-                if (_imeProcess != null)
-                {
-                    try { _imeProcess.Exited -= OnImeExited; } catch { }
-                    _imeProcess.Dispose();
-                    _imeProcess = null;
-                }
+                attached = _imeProcess;
+                _imeProcess = null;
+            }
+
+            // Not under the lock: .NET holds its own lock on the Process while it delivers Exited,
+            // OnImeExited takes _lock, and Process.Dispose waits for that delivery to finish.
+            if (attached != null)
+            {
+                try { attached.Exited -= OnImeExited; } catch { }
+                try { attached.Dispose(); } catch { }
            }
        }
    }
@@ -250,5 +250,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.Ime
    {
        public long Position { get; set; }
        public long LastKnownSize { get; set; }
+
+        /// <summary>Which file the position belongs to (see <see cref="LogFilePositionTracker.Reconcile"/>); null on older state files.</summary>
+        public string FileId { get; set; }
    }
 }
@@ -13,12 +13,12 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.Ime
        private readonly Dictionary<string, FilePositionState> _positions
            = new Dictionary<string, FilePositionState>(StringComparer.OrdinalIgnoreCase);

-        /// <summary>
-        /// Gets the safe read position for a file, detecting rollover/truncation.
-        /// If the current file size is smaller than the stored position, the file
-        /// has been rotated - resets to 0 to read from beginning.
-        /// Returns 0 if no position has been recorded yet.
-        /// </summary>
+        // Which file each path held when last checked (see Reconcile). Apart from _positions: a file
+        // whose identity is known but which no pass looked at yet must still count as unseen for
+        // HasSeen. A null value means the identity could not be read.
+        private readonly Dictionary<string, string> _fileIds
+            = new Dictionary<string, string>(StringComparer.OrdinalIgnoreCase);
+
        /// <summary>
        /// Whether this file was already observed in an earlier pass.
        /// <para>
@@ -31,6 +31,112 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.Ime
        /// </summary>
        public bool HasSeen(string filePath) => _positions.ContainsKey(filePath);

+        /// <summary>Whether <see cref="Reconcile"/> already looked at this path.</summary>
+        public bool HasIdentity(string filePath) => _fileIds.ContainsKey(filePath);
+
+        /// <summary>The identity recorded for this path, or null.</summary>
+        public string GetFileId(string filePath)
+        {
+            string id;
+            return _fileIds.TryGetValue(filePath, out id) ? id : null;
+        }
+
+        /// <summary>Restores a persisted identity. <see cref="Reconcile"/> checks it against the disk on the next pass.</summary>
+        public void RestoreFileId(string filePath, string fileId)
+        {
+            if (fileId != null) _fileIds[filePath] = fileId;
+        }
+
+        /// <summary>True when the file is smaller than its bookmark: it was rolled over or truncated.</summary>
+        public bool IsBehindBookmark(string filePath, long currentFileSize)
+        {
+            FilePositionState state;
+            return _positions.TryGetValue(filePath, out state) && currentFileSize < state.Position;
+        }
+
+        /// <summary>
+        /// Brings the bookmarks in line with the files on disk. A bookmark belongs to a file, not to
+        /// a name: IME rolls a log by renaming it, so a known file under a new path keeps its
+        /// position and only the bytes behind it are still unread. The old path starts at 0 with
+        /// whatever file it holds next, and keeps its freshness reference because that file was
+        /// written since the last look. Returns the moves.
+        /// <list type="bullet">
+        ///   <item>A file that is still at its old path as well (a hard link) moves nothing.</item>
+        ///   <item>A path that holds another file with no bookmark to take over starts at 0, even
+        ///     when the new file is longer than the old position.</item>
+        ///   <item>An unreadable identity (null) changes nothing, the path keeps its bookmark.</item>
+        /// </list>
+        /// </summary>
+        public List<BookmarkMove> Reconcile(IDictionary<string, string> idByPath)
+        {
+            var moves = new List<BookmarkMove>();
+            var claimed = new HashSet<string>(StringComparer.OrdinalIgnoreCase);
+            foreach (var entry in idByPath)
+            {
+                if (entry.Value == null || GetFileId(entry.Key) == entry.Value) continue;
+                var holder = FindBookmarkLeftBehind(entry.Value, entry.Key, idByPath);
+                if (holder != null && claimed.Add(holder))
+                    moves.Add(new BookmarkMove(holder, entry.Key, _positions[holder].Position));
+            }
+
+            // In two steps: a path can be source and target at once (X.log becomes _X.log while
+            // _X.log's own file was replaced).
+            var movedStates = new List<FilePositionState>();
+            foreach (var move in moves)
+            {
+                var state = _positions[move.From];
+                movedStates.Add(state);
+                _positions[move.From] = new FilePositionState { LastCheckedUtc = state.LastCheckedUtc };
+                _fileIds.Remove(move.From);
+            }
+            for (var i = 0; i < moves.Count; i++)
+            {
+                _positions[moves[i].To] = movedStates[i];
+                _fileIds[moves[i].To] = idByPath[moves[i].To];
+            }
+
+            foreach (var entry in idByPath)
+            {
+                if (entry.Value == null)
+                {
+                    if (!_fileIds.ContainsKey(entry.Key)) _fileIds[entry.Key] = null;
+                    continue;
+                }
+
+                string known;
+                FilePositionState state;
+                if (_fileIds.TryGetValue(entry.Key, out known) && known != null && known != entry.Value
+                    && _positions.TryGetValue(entry.Key, out state))
+                {
+                    state.Position = 0;
+                    state.LastKnownSize = 0;
+                }
+                _fileIds[entry.Key] = entry.Value;
+            }
+
+            return moves;
+        }
+
+        private string FindBookmarkLeftBehind(string fileId, string newPath, IDictionary<string, string> idByPath)
+        {
+            foreach (var known in _fileIds)
+            {
+                if (known.Value != fileId || string.Equals(known.Key, newPath, StringComparison.OrdinalIgnoreCase)) continue;
+                if (!_positions.ContainsKey(known.Key)) continue;
+
+                string stillThere;
+                if (idByPath.TryGetValue(known.Key, out stillThere) && stillThere == fileId) continue;
+                return known.Key;
+            }
+            return null;
+        }
+
+        /// <summary>
+        /// Gets the safe read position for a file, detecting rollover/truncation.
+        /// If the current file size is smaller than the stored position, the file
+        /// has been rotated - resets to 0 to read from beginning.
+        /// Returns 0 if no position has been recorded yet.
+        /// </summary>
        public long GetSafePosition(string filePath, long currentFileSize)
        {
            FilePositionState state;
@@ -144,6 +250,21 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.Ime
        }
    }

+    /// <summary>One bookmark that followed its file to a new path.</summary>
+    public sealed class BookmarkMove
+    {
+        public BookmarkMove(string from, string to, long position)
+        {
+            From = from;
+            To = to;
+            Position = position;
+        }
+
+        public string From { get; }
+        public string To { get; }
+        public long Position { get; }
+    }
+
    public class FilePositionState
    {
        public long Position { get; set; }
@@ -114,6 +114,13 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals
    /// fire once; <see cref="RealmJoinPackageStarted"/> / <see cref="RealmJoinPackageCompleted"/>
    /// fire once per <c>(scope, packageId)</c>.
    /// </para>
+    /// <para>
+    /// <see cref="RealmJoinDetected"/> carries the phase RJ is in when the service key is first
+    /// seen in this process — Blank (0) only while the value is not written yet. After an agent
+    /// restart RJ may already be deploying: the engine's restart path and the keep-awake
+    /// hand-over to RJ both read the phase from Detected, because no PhaseChanged follows when
+    /// the phase does not change again.
+    /// </para>
    /// </remarks>
    internal sealed class RealmJoinWatcher : IDisposable
    {
@@ -127,6 +134,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals
        internal delegate bool KeyExistsDelegate(RegistryHive hive, string subPath);
        internal delegate RealmJoinVersionInfo ReadVersionInfoDelegate();
        internal delegate string? ReadUninstallDisplayVersionDelegate();
+        internal delegate int? ReadDeploymentPhaseDelegate();

        /// <summary>
        /// Debounce for the Uninstall-key watcher. Longer than <see cref="DebounceMilliseconds"/>:
@@ -141,6 +149,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals
        private readonly KeyExistsDelegate _keyExists;
        private readonly ReadVersionInfoDelegate _readVersionInfo;
        private readonly ReadUninstallDisplayVersionDelegate _readUninstallDisplayVersion;
+        private readonly ReadDeploymentPhaseDelegate _readDeploymentPhase;
        private readonly object _stateLock = new object();

        // Auto-update stage (armed once Detected fired, held until Stop).
@@ -185,6 +194,9 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals
        // subtree) into RJ's lifecycle.
        private bool _packageWatchersArmed;
        private bool _disposed;
+        // Set by Stop under _stateLock: a registry callback that is still running then must not
+        // arm or attach another watcher.
+        private bool _stopped;

        public event EventHandler<RealmJoinDetectedEventArgs>? RealmJoinDetected;
        public event EventHandler<RealmJoinResolvedEventArgs>? RealmJoinResolved;
@@ -204,7 +216,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals
            TryReadPackageDelegate tryReadPackage,
            KeyExistsDelegate keyExists,
            ReadVersionInfoDelegate? readVersionInfo = null,
-            ReadUninstallDisplayVersionDelegate? readUninstallDisplayVersion = null)
+            ReadUninstallDisplayVersionDelegate? readUninstallDisplayVersion = null,
+            ReadDeploymentPhaseDelegate? readDeploymentPhase = null)
        {
            _logger = logger ?? throw new ArgumentNullException(nameof(logger));
            _enumeratePackageIds = enumeratePackageIds ?? throw new ArgumentNullException(nameof(enumeratePackageIds));
@@ -212,11 +225,13 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals
            _keyExists = keyExists ?? throw new ArgumentNullException(nameof(keyExists));
            _readVersionInfo = readVersionInfo ?? RealmJoinInfo.TryReadRealmJoinVersionInfo;
            _readUninstallDisplayVersion = readUninstallDisplayVersion ?? RealmJoinInfo.TryReadUninstallDisplayVersion;
+            _readDeploymentPhase = readDeploymentPhase ?? (() => RealmJoinInfo.TryReadDeploymentPhase(RegistryHive.LocalMachine));
        }

        public void Start()
        {
            if (_disposed) throw new ObjectDisposedException(nameof(RealmJoinWatcher));
+            lock (_stateLock) { _stopped = false; }

            // The Services\realmjoin gate is the SOLE entry point. HKLM\SOFTWARE\RealmJoin and
            // the HKU watcher do not run until this fires — RJ presence is the prerequisite for
@@ -266,27 +281,37 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals
        {
            try
            {
-                var stoppedAny = false;
+                var watchers = new List<RegistryWatcher>(8);
                lock (_stateLock)
                {
-                    stoppedAny |= DisposeAndNull(ref _servicesAppearanceWatcher);
-                    stoppedAny |= DisposeAndNull(ref _machineSoftwareAppearanceWatcher);
-                    stoppedAny |= DisposeAndNull(ref _userSoftwareAppearanceWatcher);
-                    stoppedAny |= DisposeAndNull(ref _uninstallAppearanceWatcher);
+                    _stopped = true;
+
+                    Take(ref _servicesAppearanceWatcher, watchers);
+                    Take(ref _machineSoftwareAppearanceWatcher, watchers);
+                    Take(ref _userSoftwareAppearanceWatcher, watchers);
+                    Take(ref _uninstallAppearanceWatcher, watchers);

                    _serviceRealmjoinDebounce?.Dispose(); _serviceRealmjoinDebounce = null;
                    _machineRealmJoinDebounce?.Dispose(); _machineRealmJoinDebounce = null;
                    _userRealmJoinDebounce?.Dispose(); _userRealmJoinDebounce = null;
                    _uninstallDebounce?.Dispose(); _uninstallDebounce = null;

-                    stoppedAny |= DisposeAndNull(ref _serviceRealmjoinWatcher);
-                    stoppedAny |= DisposeAndNull(ref _machineRealmJoinWatcher);
-                    stoppedAny |= DisposeAndNull(ref _userRealmJoinWatcher);
-                    stoppedAny |= DisposeAndNull(ref _uninstallWatcher);
+                    Take(ref _serviceRealmjoinWatcher, watchers);
+                    Take(ref _machineRealmJoinWatcher, watchers);
+                    Take(ref _userRealmJoinWatcher, watchers);
+                    Take(ref _uninstallWatcher, watchers);
                }
+
+                // Disposed outside the lock: RegistryWatcher.Dispose waits for a callback that is
+                // still running, and the appearance callback takes _stateLock.
+                foreach (var watcher in watchers)
+                {
+                    try { watcher.Dispose(); } catch { }
+                }
+
                // Hosts call Stop and then Dispose, which stops again; only the pass that
                // stopped a watcher logs.
-                if (stoppedAny) _logger.Info($"RealmJoinWatcher: stopped ({reason})");
+                if (watchers.Count > 0) _logger.Info($"RealmJoinWatcher: stopped ({reason})");
            }
            catch (Exception ex)
            {
@@ -380,6 +405,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals
            Action clearSlot,
            Action onAppeared)
        {
+            lock (_stateLock) { if (_stopped) return; }
            try
            {
                var watcher = new RegistryWatcher(
@@ -429,7 +455,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals
        {
            lock (_stateLock)
            {
-                if (_serviceRealmjoinWatcher != null) return;
+                if (_stopped || _serviceRealmjoinWatcher != null) return;
                try
                {
                    _serviceRealmjoinDebounce = new Timer(_ => CheckParameters(), null, Timeout.Infinite, Timeout.Infinite);
@@ -452,21 +478,30 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals
                }
            }

-            // The appearance of Services\realmjoin is itself the RJ-detected signal —
-            // surface it even if Parameters\DeploymentPhase isn't populated yet. The package
-            // watchers (HKLM + HKU SOFTWARE\RealmJoin) intentionally stay disarmed here:
-            // NotifyRealmJoinPresence arms them once DeploymentPhase >= PhaseRunningThresholdMin
-            // is observed. Before that the same subtree may still receive in-flight IME
-            // package writes that are not part of RJ's lifecycle.
-            NotifyRealmJoinPresence(phase: null);
-            CheckParameters();
+            NotifyServiceStageAttached();
+        }
+
+        /// <summary>
+        /// The appearance of Services\realmjoin is itself the RJ-detected signal — surfaced even
+        /// if Parameters\DeploymentPhase isn't populated yet. One read feeds Detected, so it
+        /// carries the phase RJ is in right now (see the class remarks). The package watchers
+        /// (HKLM + HKU SOFTWARE\RealmJoin) stay disarmed below PhaseRunningThresholdMin: before
+        /// that the same subtree may still receive in-flight IME package writes that are not
+        /// part of RJ's lifecycle.
+        /// </summary>
+        private void NotifyServiceStageAttached()
+        {
+            int? phase = null;
+            try { phase = _readDeploymentPhase(); }
+            catch (Exception ex) { _logger.Warning($"RealmJoinWatcher: DeploymentPhase read at attach threw: {ex.Message}"); }
+            NotifyRealmJoinPresence(phase);
        }

        private void AttachMachineRealmJoinSubtreeWatcher()
        {
            lock (_stateLock)
            {
-                if (_machineRealmJoinWatcher != null) return;
+                if (_stopped || _machineRealmJoinWatcher != null) return;
                try
                {
                    // Seed dedup sets with every package sub-key already present at arming time.
@@ -509,7 +544,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals
        {
            lock (_stateLock)
            {
-                if (_userRealmJoinWatcher != null) return;
+                if (_stopped || _userRealmJoinWatcher != null) return;
                try
                {
                    // Seed dedup sets — see AttachMachineRealmJoinSubtreeWatcher for rationale.
@@ -550,7 +585,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals
        {
            try
            {
-                var phase = RealmJoinInfo.TryReadDeploymentPhase(RegistryHive.LocalMachine);
+                var phase = _readDeploymentPhase();
                if (phase == null) return;
                NotifyRealmJoinPresence(phase);
            }
@@ -580,6 +615,11 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals
                fireDetected = !_detectedFired;
                if (fireDetected) _detectedFired = true;

+                // Detected reports Blank (0) while the value is not written yet. That report is
+                // the baseline, so a first real value of 100+ surfaces as PhaseChanged instead of
+                // silently setting _lastPhase.
+                if (fireDetected && !phase.HasValue && !_lastPhase.HasValue) _lastPhase = 0;
+
                if (phase.HasValue)
                {
                    if (_lastPhase.HasValue && _lastPhase.Value != phase.Value)
@@ -686,7 +726,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals
        {
            lock (_stateLock)
            {
-                if (_disposed || _uninstallWatcher != null) return;
+                if (_disposed || _stopped || _uninstallWatcher != null) return;
                try
                {
                    _uninstallDebounce = new Timer(_ => CheckAutoUpdate(), null, Timeout.Infinite, Timeout.Infinite);
@@ -916,16 +956,17 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals
            }
        }

-        private static bool DisposeAndNull(ref RegistryWatcher? w)
+        // Caller holds _stateLock; the taken watchers are disposed after it is released.
+        private static void Take(ref RegistryWatcher? slot, List<RegistryWatcher> taken)
        {
-            if (w == null) return false;
-            try { w.Dispose(); } catch { }
-            w = null;
-            return true;
+            if (slot == null) return;
+            taken.Add(slot);
+            slot = null;
        }

        // Test seams — drive the read paths deterministically without touching the real registry.
        internal void TriggerCheckParametersFromTest() => CheckParameters();
+        internal void TriggerServiceStageAttachedFromTest() => NotifyServiceStageAttached();
        internal void TriggerCheckMachinePackagesFromTest() => CheckMachinePackages();
        internal void TriggerCheckUserPackagesFromTest() => CheckUserPackages();

@@ -9,6 +9,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Interop
    /// Win32 file-handle declarations for <c>PinnedSourceFolder</c>: open a file or directory
    /// without following a reparse point at its final component, and ask the handle where it
    /// really points (<c>GetFinalPathNameByHandle</c>) instead of trusting the path string.
+    /// <c>ImeLogFileIdentity</c> reads a file's identity through the same declarations.
    /// </summary>
    internal static class FileNativeMethods
    {
@@ -18,6 +19,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Interop

        public const uint FILE_SHARE_READ = 0x1;
        public const uint FILE_SHARE_WRITE = 0x2;
+        public const uint FILE_SHARE_DELETE = 0x4;

        public const uint OPEN_EXISTING = 3;

@@ -0,0 +1,41 @@
+using System;
+using System.Runtime.InteropServices;
+
+namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Interop
+{
+    internal static class WinHttpNativeMethods
+    {
+        public const int ERROR_FILE_NOT_FOUND = 2;
+        public const uint WINHTTP_ACCESS_TYPE_NAMED_PROXY = 3;
+
+        [StructLayout(LayoutKind.Sequential)]
+        public struct WINHTTP_CURRENT_USER_IE_PROXY_CONFIG
+        {
+            [MarshalAs(UnmanagedType.Bool)]
+            public bool fAutoDetect;
+            public IntPtr lpszAutoConfigUrl;
+            public IntPtr lpszProxy;
+            public IntPtr lpszProxyBypass;
+        }
+
+        [StructLayout(LayoutKind.Sequential)]
+        public struct WINHTTP_PROXY_INFO
+        {
+            public uint dwAccessType;
+            public IntPtr lpszProxy;
+            public IntPtr lpszProxyBypass;
+        }
+
+        [DllImport("winhttp.dll", SetLastError = true)]
+        [return: MarshalAs(UnmanagedType.Bool)]
+        public static extern bool WinHttpGetIEProxyConfigForCurrentUser(ref WINHTTP_CURRENT_USER_IE_PROXY_CONFIG config);
+
+        [DllImport("winhttp.dll", SetLastError = true)]
+        [return: MarshalAs(UnmanagedType.Bool)]
+        public static extern bool WinHttpGetDefaultProxyConfiguration(ref WINHTTP_PROXY_INFO info);
+
+        // WinHTTP allocates the strings of both structs with GlobalAlloc; the caller frees them.
+        [DllImport("kernel32.dll", SetLastError = true)]
+        public static extern IntPtr GlobalFree(IntPtr hMem);
+    }
+}
@@ -1,5 +1,6 @@
 using System;
 using System.Collections.Generic;
+using System.Globalization;
 using System.IO;
 using System.Linq;
 using System.Management;
@@ -36,21 +37,21 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Analyzers
    /// (<c>builtin_administrator_enabled</c>) but not scored: whether OOBE enables it
    /// transiently is not established, so the field first collects evidence.
    ///
-    /// Built-in accounts are recognised by well-known RID (500/501/503/504 on the machine SID)
-    /// in addition to their English names, so localized installs (Gast, Invité, Administrateur)
-    /// do not flag their own disabled Guest/Administrator.
+    /// Allowed list (<see cref="LocalAdminAllowList"/> built-ins plus the tenant's entries): an entry
+    /// allows an account in any role, or — <c>name|user</c> — only while it is not an
+    /// Administrators member. A restriction always wins over an entry that allows more. The four
+    /// built-in accounts are decided by their well-known RID alone (500 any role; 501/503/504 never
+    /// an administrator), so localized names (Gast, Administrateur) are recognised and no name entry
+    /// can lift or impose a role on them. Profile folders have no role.
    ///
-    /// At shutdown the logged-in users are allowed dynamically — but only identities that are
-    /// NOT local SAM accounts (Entra / domain users, whose profile folder is the only artifact
-    /// they leave). A logged-in local account is exactly the delta this analyzer exists to
-    /// catch and is never exempted by its own login (CWE-807: the login state is under the
+    /// At shutdown the logged-in users are allowed dynamically — as profile folders only, and only
+    /// identities that are NOT local SAM accounts (Entra / domain users, whose profile folder is the
+    /// only artifact they leave). A logged-in local account is exactly the delta this analyzer exists
+    /// to catch and is never exempted by its own login (CWE-807: the login state is under the
    /// adversary's control); it is reported as <c>logged_in_local_accounts</c>.
    ///
    /// Emits a single "local_admin_analysis" event at startup and at shutdown,
    /// enabling delta detection between pre- and post-enrollment state.
-    ///
-    /// Tenant-supplied allowed accounts may contain glob wildcards (e.g. "adm-*");
-    /// see <see cref="MatchesAllowedEntry"/>.
    /// </summary>
    public class LocalAdminAnalyzer : IAgentAnalyzer
    {
@@ -58,26 +59,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Analyzers
        private readonly string _tenantId;
        private readonly InformationalEventPost _post;
        private readonly AgentLogger _logger;
-        private readonly List<string> _allowedAccounts;
-
-        // Built-in accounts and profile folders always present on a freshly imaged Windows device.
-        // "Public", "Default", "Default User", "All Users" are folders/junctions in C:\Users, not user accounts.
-        // "defaultuser0" is a temporary OOBE/Autopilot system account created during enrollment.
-        private static readonly List<string> BuiltInAllowedAccounts = new List<string>
-        {
-            "Administrator",
-            "Guest",
-            "DefaultAccount",
-            "WDAGUtilityAccount",
-            "defaultuser0",    // Temporary OOBE/Autopilot system account, present during enrollment
-            "defaultuser1",    // Sometimes seen in OOBE, but not always present
-            "defaultuser2",    // Sometimes seen in OOBE, but not always present
-            "kioskUser0",      // Assigned Access (kiosk profile) autologon account, created by Windows
-            "Public",          // Profile folder (not a user account)
-            "Default",         // Default user profile template
-            "Default User",    // Symlink to Default in some Windows versions
-            "All Users"        // Junction pointing to C:\ProgramData, always present
-        };
+        private readonly List<AllowedEntry> _allowedEntries;

        public string Name => "LocalAdminAnalyzer";

@@ -97,19 +79,10 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Analyzers
            _logger    = logger    ?? throw new ArgumentNullException(nameof(logger));
            _startupGate = startupGate;

-            // Tenant-supplied accounts are additive (union with built-ins, not replacement)
-            _allowedAccounts = new List<string>(BuiltInAllowedAccounts);
-            if (allowedAccounts != null)
-            {
-                foreach (var account in allowedAccounts)
-                {
-                    if (!string.IsNullOrWhiteSpace(account) &&
-                        !_allowedAccounts.Any(a => string.Equals(a, account, StringComparison.OrdinalIgnoreCase)))
-                    {
-                        _allowedAccounts.Add(account);
-                    }
-                }
-            }
+            var ignored = new List<string>();
+            _allowedEntries = BuildAllowedEntries(allowedAccounts, ignored);
+            foreach (var entry in ignored)
+                _logger.Warning($"{Name}: Allowed-list entry '{entry}' is not valid (expected 'name' or 'name|user') — ignored, it allows nothing");
        }

        public void AnalyzeAtStartup()
@@ -149,46 +122,29 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Analyzers
                foreach (var user in loggedIn.LocalAccounts)
                    _logger.Warning($"{Name}: Logged-in user '{user}' is a local account — not allowed dynamically");

-                // Build effective allowed list: static + dynamic (non-local logged-in users at shutdown)
-                var effectiveAllowed = _allowedAccounts;
+                // Effective list: static entries + the profile folders of non-local logged-in users at
+                // shutdown. Folder-only: a login never allows a local ACCOUNT — not even when the WMI
+                // inventory failed and the split above could not recognise a local name.
+                var effectiveEntries = _allowedEntries;
                if (loggedIn.Allowed.Count > 0)
                {
-                    effectiveAllowed = new List<string>(_allowedAccounts);
+                    effectiveEntries = new List<AllowedEntry>(_allowedEntries);
                    foreach (var user in loggedIn.Allowed)
                    {
-                        if (!effectiveAllowed.Any(a => string.Equals(a, user, StringComparison.OrdinalIgnoreCase)))
+                        if (!effectiveEntries.Any(e => string.Equals(e.Pattern, user, StringComparison.OrdinalIgnoreCase)))
                        {
-                            effectiveAllowed.Add(user);
-                            _logger.Info($"{Name}: Dynamically allowing logged-in user: {user}");
+                            effectiveEntries.Add(new AllowedEntry(user, LocalAccountRole.Any, profileFolderOnly: true));
+                            _logger.Info($"{Name}: Dynamically allowing profile folder of logged-in user: {user}");
                        }
                    }
                }

                var bypassNroResult  = CheckBypassNroRegistry();
-                var accountsResult   = CheckLocalAdminAccounts(localAccounts, effectiveAllowed);
-                var profilesResult   = CheckUserProfiles(effectiveAllowed);
+                var accountsResult   = CheckLocalAdminAccounts(localAccounts, effectiveEntries);
+                var profilesResult   = CheckUserProfiles(effectiveEntries);

-                int confidenceScore = 0;
-
-                if (bypassNroResult.Value == 1)
-                    confidenceScore += 20;
-
-                if (accountsResult.Unexpected.Count > 0)
-                    confidenceScore += 40;
-
-                // An unexpected account that is also a member of Administrators is the
-                // actual backdoor (enabled or dormant) — high indicator on its own.
-                if (accountsResult.UnexpectedAdminMembers.Count > 0)
-                    confidenceScore += 40;
-
-                // Profile overlap: unexpected account AND matching C:\Users folder
-                bool profileOverlap = accountsResult.Unexpected.Any(a =>
-                    profilesResult.Unexpected.Any(p =>
-                        string.Equals(a, p, StringComparison.OrdinalIgnoreCase)));
-                if (profileOverlap)
-                    confidenceScore += 40;
-
-                confidenceScore = Math.Min(confidenceScore, 100);
+                var confidenceScore = ComputeConfidenceScore(
+                    bypassNroResult.Value == 1, accountsResult.Unexpected, accountsResult.UnexpectedAdminMembers, profilesResult.Unexpected);

                EventSeverity severity;
                string findingLabel;
@@ -219,6 +175,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Analyzers
                    $"bypassNro={bypassNroResult.Value}, " +
                    $"unexpectedAccounts={accountsResult.Unexpected.Count}, " +
                    $"unexpectedAdminMembers={accountsResult.UnexpectedAdminMembers.Count}, " +
+                    $"roleViolations={accountsResult.RoleViolations.Count}, " +
                    $"adminGroupEnumerated={accountsResult.AdministratorsGroupEnumerated}, " +
                    $"builtinAdministratorEnabled={accountsResult.BuiltInAdministratorEnabled?.ToString() ?? "unknown"}, " +
                    $"unexpectedProfiles={profilesResult.Unexpected.Count}");
@@ -230,7 +187,9 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Analyzers
                    { "finding",                    findingLabel },
                    { "triggered_at",               trigger },
                    { "enrollment_phase_at_check",  phase.ToString() },
-                    { "allowed_accounts",           effectiveAllowed },
+                    // Account entries in canonical form ("Guest|user"); the folder-only entries are
+                    // constant or listed in dynamically_allowed_users.
+                    { "allowed_accounts",           _allowedEntries.Where(e => !e.ProfileFolderOnly).Select(e => e.Display).ToList() },
                    { "dynamically_allowed_users",  loggedIn.Allowed },
                    { "logged_in_local_accounts",   loggedIn.LocalAccounts },
                    { "checks", new Dictionary<string, object>
@@ -243,6 +202,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Analyzers
                            },
                            { "unexpected_accounts",  accountsResult.Unexpected },
                            { "unexpected_admin_members", accountsResult.UnexpectedAdminMembers },
+                            { "role_violations",      accountsResult.RoleViolations },
                            { "unexpected_profiles",  profilesResult.Unexpected },
                            { "accounts_checked",     accountsResult.AllChecked },
                            { "account_details",      accountsResult.AccountDetails },
@@ -299,31 +259,53 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Analyzers
            }
        }

+        /// <summary>
+        /// Confidence 0-100: BypassNRO +20, any unexpected account +40, any unexpected Administrators
+        /// member +40 (the actual backdoor, enabled or dormant; a role violation is one), an unexpected
+        /// account with a C:\Users folder of the same name +40. Pure; internal for unit-testing.
+        /// </summary>
+        internal static int ComputeConfidenceScore(
+            bool bypassNro, IList<string> unexpectedAccounts, IList<string> unexpectedAdminMembers, IList<string> unexpectedProfiles)
+        {
+            var score = 0;
+            if (bypassNro)
+                score += 20;
+            if (unexpectedAccounts.Count > 0)
+                score += 40;
+            if (unexpectedAdminMembers.Count > 0)
+                score += 40;
+            if (unexpectedAccounts.Any(a => unexpectedProfiles.Any(p => string.Equals(a, p, StringComparison.OrdinalIgnoreCase))))
+                score += 40;
+            return Math.Min(score, 100);
+        }
+
        // -----------------------------------------------------------------------
        // Allowed-list matching
        // -----------------------------------------------------------------------

        /// <summary>
-        /// Matches an account or profile-folder name against one allowed-list entry.
-        /// Entries containing <c>*</c> or <c>?</c> are glob patterns (same semantics as the
+        /// Matches an account or profile-folder name against one allowed-list pattern.
+        /// Patterns containing <c>*</c> or <c>?</c> are globs (same semantics as the
        /// hardware whitelist: <c>*</c> = any run, <c>?</c> = one char, case-insensitive);
-        /// all other entries match exactly. No ambiguity with literal names — <c>*</c> and
+        /// all other patterns match exactly. No ambiguity with literal names — <c>*</c> and
        /// <c>?</c> are invalid characters in Windows account names.
        /// Internal for direct unit-testing via InternalsVisibleTo.
        /// </summary>
-        internal static bool MatchesAllowedEntry(string name, string entry)
+        internal static bool MatchesAllowedEntry(string name, string pattern)
        {
-            if (entry.IndexOf('*') < 0 && entry.IndexOf('?') < 0)
-                return string.Equals(entry, name, StringComparison.OrdinalIgnoreCase);
+            if (pattern.IndexOf('*') < 0 && pattern.IndexOf('?') < 0)
+                return string.Equals(pattern, name, StringComparison.OrdinalIgnoreCase);

-            var regexPattern = "^" + Regex.Escape(entry)
+            var regexPattern = "^" + Regex.Escape(pattern)
                .Replace("\\*", ".*")
                .Replace("\\?", ".") + "$";

            try
            {
-                // Timeout guards against pathological patterns (ReDoS)
-                return Regex.IsMatch(name, regexPattern, RegexOptions.IgnoreCase, TimeSpan.FromMilliseconds(100));
+                // Timeout guards against pathological patterns (ReDoS). CultureInvariant: under a
+                // Turkish culture "i" and "I" are no case pair, so "WLapsAdmin*" missed "WLAPSADMIN01".
+                return Regex.IsMatch(name, regexPattern, RegexOptions.IgnoreCase | RegexOptions.CultureInvariant,
+                    TimeSpan.FromMilliseconds(100));
            }
            catch (RegexMatchTimeoutException)
            {
@@ -331,39 +313,107 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Analyzers
            }
        }

-        private static bool IsAllowed(string name, List<string> allowedAccounts)
+        /// <summary>
+        /// The effective static list: the built-in account-name and profile-folder entries of
+        /// <see cref="LocalAdminAllowList.BuiltIns"/> (RID entries are decided by RID, see
+        /// <see cref="Decide"/>) plus the tenant's entries. An entry that does not parse is added to
+        /// <paramref name="ignored"/> and allows nothing. Pure; internal for unit-testing.
+        /// </summary>
+        internal static List<AllowedEntry> BuildAllowedEntries(IEnumerable<string> tenantEntries, List<string> ignored)
        {
-            return allowedAccounts.Any(a => MatchesAllowedEntry(name, a));
+            var entries = new List<AllowedEntry>();
+            foreach (var builtIn in LocalAdminAllowList.BuiltIns)
+            {
+                if (builtIn.Match == LocalAdminBuiltInMatch.AccountName)
+                    AddDistinct(entries, new AllowedEntry(builtIn.Name, builtIn.Role, profileFolderOnly: false));
+                else if (builtIn.Match == LocalAdminBuiltInMatch.ProfileFolder)
+                    AddDistinct(entries, new AllowedEntry(builtIn.Name, LocalAccountRole.Any, profileFolderOnly: true));
+            }
+
+            foreach (var raw in tenantEntries ?? Enumerable.Empty<string>())
+            {
+                if (LocalAdminAllowList.TryParseEntry(raw, out var pattern, out var role))
+                    AddDistinct(entries, new AllowedEntry(pattern, role, profileFolderOnly: false));
+                else if (!string.IsNullOrWhiteSpace(raw))
+                    ignored.Add(raw);
+            }
+
+            return entries;
+        }
+
+        private static void AddDistinct(List<AllowedEntry> entries, AllowedEntry entry)
+        {
+            if (!entries.Any(e => e.ProfileFolderOnly == entry.ProfileFolderOnly
+                                  && string.Equals(e.Display, entry.Display, StringComparison.OrdinalIgnoreCase)))
+                entries.Add(entry);
        }

        /// <summary>
-        /// Well-known built-in accounts of the local machine domain, recognised by RID so that
-        /// localized names (Gast, Invité, Administrateur, …) are not flagged:
-        /// 500 Administrator, 501 Guest, 503 DefaultAccount, 504 WDAGUtilityAccount.
-        /// Only S-1-5-21-… SIDs qualify (the WMI query is already restricted to local accounts).
+        /// Decides one local account. The built-in accounts are decided by their RID alone: 500 in any
+        /// role, 501/503/504 never as an administrator — no name entry, built-in or tenant, lifts or
+        /// imposes a role on them. Without a SID (a WMI corner case) the English name stands in for the
+        /// RID. Every other account is allowed when an account entry matches it, unless it is an
+        /// administrator and ANY matching entry is standard-user only: a restriction always wins.
+        /// Pure; internal for unit-testing.
+        /// </summary>
+        internal static AccountDecision Decide(string name, string sid, bool isAdmin, IReadOnlyList<AllowedEntry> allowed)
+        {
+            var builtIn = FindBuiltInRidEntry(name, sid);
+            if (builtIn != null)
+                return isAdmin && builtIn.Role == LocalAccountRole.StandardUser ? AccountDecision.RoleViolation : AccountDecision.Allowed;
+
+            var covered = false;
+            var restricted = false;
+            foreach (var entry in allowed)
+            {
+                if (entry.ProfileFolderOnly || !MatchesAllowedEntry(name, entry.Pattern))
+                    continue;
+                covered = true;
+                if (entry.Role == LocalAccountRole.StandardUser)
+                    restricted = true;
+            }
+
+            if (!covered)
+                return AccountDecision.Unlisted;
+            return isAdmin && restricted ? AccountDecision.RoleViolation : AccountDecision.Allowed;
+        }
+
+        private static LocalAdminBuiltInEntry FindBuiltInRidEntry(string name, string sid)
+        {
+            var rid = MachineAccountRid(sid);
+            foreach (var builtIn in LocalAdminAllowList.BuiltIns)
+            {
+                if (builtIn.Match != LocalAdminBuiltInMatch.Rid)
+                    continue;
+                var matches = rid.HasValue
+                    ? builtIn.Rid == rid.Value
+                    : string.IsNullOrEmpty(sid) && string.Equals(builtIn.Name, name, StringComparison.OrdinalIgnoreCase);
+                if (matches)
+                    return builtIn;
+            }
+            return null;
+        }
+
+        /// <summary>
+        /// RID (the last sub-authority) of a local-machine account SID (<c>S-1-5-21-…</c>; the WMI query
+        /// and the member filter already restrict to local accounts), else null.
        /// Internal for direct unit-testing via InternalsVisibleTo.
        /// </summary>
-        internal static bool IsWellKnownBuiltInRid(string sid)
+        internal static int? MachineAccountRid(string sid)
        {
            if (string.IsNullOrEmpty(sid) || !sid.StartsWith("S-1-5-21-", StringComparison.Ordinal))
-                return false;
+                return null;

            var dash = sid.LastIndexOf('-');
-            if (dash < 0 || dash == sid.Length - 1)
-                return false;
-
-            switch (sid.Substring(dash + 1))
-            {
-                case "500":
-                case "501":
-                case "503":
-                case "504":
-                    return true;
-                default:
-                    return false;
-            }
+            return int.TryParse(sid.Substring(dash + 1), NumberStyles.None, CultureInfo.InvariantCulture, out var rid)
+                ? rid
+                : (int?)null;
        }

+        /// <summary>A profile folder has no role: any entry of the same name allows it.</summary>
+        private static bool IsAllowedFolder(string folderName, IReadOnlyList<AllowedEntry> allowed)
+            => allowed.Any(e => MatchesAllowedEntry(folderName, e.Pattern));
+
        /// <summary>
        /// Splits the logged-in user names into those that may be allowed dynamically (not a
        /// local SAM account — Entra / domain identities whose only artifact is a profile
@@ -481,7 +531,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Analyzers
            return accounts;
        }

-        private LocalAccountCheckResult CheckLocalAdminAccounts(List<LocalAccountInfo> accounts, List<string> allowedAccounts)
+        private LocalAccountCheckResult CheckLocalAdminAccounts(List<LocalAccountInfo> accounts, IReadOnlyList<AllowedEntry> allowed)
        {
            // Administrators-group membership is read from the SAM, independent of WMI and of
            // the enabled state — a dormant backdoor with admin rights is still a member.
@@ -489,13 +539,15 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Analyzers
            if (!group.Succeeded)
                _logger.Warning($"{Name}: Failed to enumerate members of '{group.GroupName}': NET_API_STATUS={group.ErrorCode}");

-            var result = EvaluateAccounts(accounts, group.Members, group.Succeeded, Environment.MachineName, allowedAccounts);
+            var result = EvaluateAccounts(accounts, group.Members, group.Succeeded, Environment.MachineName, allowed);
            result.AdministratorsGroupErrorCode = group.ErrorCode;

            foreach (var name in result.Unexpected)
                _logger.Debug($"{Name}: Unexpected local account: {name}");
            foreach (var name in result.UnexpectedAdminMembers)
                _logger.Debug($"{Name}: Unexpected Administrators member: {name}");
+            foreach (var name in result.RoleViolations)
+                _logger.Debug($"{Name}: Allowed only as a standard user but an Administrators member: {name}");

            return result;
        }
@@ -508,10 +560,13 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Analyzers
        ///   - every local account is checked, disabled ones included (state is reported);
        ///   - a local account is an Administrators member when its SID matches a group member,
        ///     or (SID unavailable) its name matches a member of the local machine domain;
-        ///   - an account is allowed by name (allowed list, globs) or by well-known RID
-        ///     (<see cref="IsWellKnownBuiltInRid"/>) — localized built-ins are never flagged;
-        ///   - <c>UnexpectedAdminMembers</c> = unexpected accounts holding membership, plus local
-        ///     members not on the allowed list that the WMI inventory did not return at all;
+        ///   - each account is decided by <see cref="Decide"/>; an account no entry allows, or one
+        ///     that breaks a standard-user entry, is unexpected (and an unexpected admin when it
+        ///     holds membership; the latter also a role violation);
+        ///   - local members the WMI inventory did not return at all are decided as administrators
+        ///     and land in both unexpected lists, like any unknown administrator;
+        ///   - with membership unknown (enumeration failed) nobody counts as an administrator, so a
+        ///     standard-user entry acts like a plain one;
        ///   - members outside the local machine domain (Entra role SIDs, domain groups) are
        ///     listed for delta comparison but never flagged — they are expected on joined devices.
        /// </summary>
@@ -520,7 +575,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Analyzers
            IList<LocalGroupMember> adminMembers,
            bool adminGroupEnumerated,
            string machineName,
-            List<string> allowedAccounts)
+            IReadOnlyList<AllowedEntry> allowed)
        {
            var result = new LocalAccountCheckResult { AdministratorsGroupEnumerated = adminGroupEnumerated };

@@ -539,45 +594,65 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Analyzers
                }
            }

+            var inventorySids = new HashSet<string>(StringComparer.OrdinalIgnoreCase);
+            var inventoryNames = new HashSet<string>(StringComparer.OrdinalIgnoreCase);
            foreach (var account in accounts ?? new List<LocalAccountInfo>())
            {
                var isAdmin = (!string.IsNullOrEmpty(account.Sid) && adminSids.Contains(account.Sid))
                              || adminLocalNames.Contains(account.Name);
+                var rid = MachineAccountRid(account.Sid);
+
+                if (!string.IsNullOrEmpty(account.Sid))
+                    inventorySids.Add(account.Sid);
+                inventoryNames.Add(account.Name);

                result.AllChecked.Add(account.Name);
                result.AccountDetails.Add(new Dictionary<string, object>
                {
                    { "name",                  account.Name },
                    { "disabled",              account.Disabled },
-                    { "administrators_member", isAdmin }
+                    { "administrators_member", isAdmin },
+                    { "rid",                   rid }
                });

-                if (account.Sid != null && account.Sid.EndsWith("-500", StringComparison.Ordinal))
+                if (rid == 500)
                    result.BuiltInAdministratorEnabled = !account.Disabled;

-                if (IsWellKnownBuiltInRid(account.Sid) || IsAllowed(account.Name, allowedAccounts))
-                    continue;
-
-                result.Unexpected.Add(account.Name);
-                if (isAdmin)
-                    result.UnexpectedAdminMembers.Add(account.Name);
+                Record(result, account.Name, Decide(account.Name, account.Sid, isAdmin, allowed), isAdmin);
            }

            // Local members the WMI inventory did not surface (WMI failure, or an account the
-            // provider does not list) — still an unexpected admin when not on the allowed list.
+            // provider does not list): the SAM is authoritative for membership.
            foreach (var member in adminLocalMembers)
            {
-                var name = member.Name;
-                if (IsWellKnownBuiltInRid(member.Sid) || IsAllowed(name, allowedAccounts))
+                var returnedByWmi = !string.IsNullOrEmpty(member.Sid)
+                    ? inventorySids.Contains(member.Sid)
+                    : inventoryNames.Contains(member.Name);
+                if (returnedByWmi)
                    continue;
-                if (result.UnexpectedAdminMembers.Any(u => string.Equals(u, name, StringComparison.OrdinalIgnoreCase)))
-                    continue;
-                result.UnexpectedAdminMembers.Add(name);
+                Record(result, member.Name, Decide(member.Name, member.Sid, isAdmin: true, allowed), isAdmin: true);
            }

            return result;
        }

+        private static void Record(LocalAccountCheckResult result, string name, AccountDecision decision, bool isAdmin)
+        {
+            if (decision == AccountDecision.Allowed)
+                return;
+            AddOnce(result.Unexpected, name);
+            if (isAdmin)
+                AddOnce(result.UnexpectedAdminMembers, name);
+            if (decision == AccountDecision.RoleViolation)
+                AddOnce(result.RoleViolations, name);
+        }
+
+        private static void AddOnce(List<string> names, string name)
+        {
+            if (!names.Any(n => string.Equals(n, name, StringComparison.OrdinalIgnoreCase)))
+                names.Add(name);
+        }
+
        private static bool IsLocalMember(LocalGroupMember member, string machineName)
        {
            var domain = member.Domain;
@@ -586,7 +661,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Analyzers
            return string.Equals(domain, machineName, StringComparison.OrdinalIgnoreCase);
        }

-        private UserProfileCheckResult CheckUserProfiles(List<string> allowedAccounts)
+        private UserProfileCheckResult CheckUserProfiles(IReadOnlyList<AllowedEntry> allowed)
        {
            var allFound   = new List<string>();
            var unexpected = new List<string>();
@@ -616,7 +691,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Analyzers

                    allFound.Add(folderName);

-                    if (!IsAllowed(folderName, allowedAccounts))
+                    if (!IsAllowedFolder(folderName, allowed))
                    {
                        unexpected.Add(folderName);
                        _logger.Debug($"{Name}: Unexpected profile folder: {folderName}");
@@ -740,7 +815,10 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Analyzers
            /// <summary>Unexpected accounts that are members of the Administrators group.</summary>
            public List<string> UnexpectedAdminMembers { get; set; } = new List<string>();

-            /// <summary>Per-account state: name, disabled, administrators_member.</summary>
+            /// <summary>Administrators members that an entry allows only as a standard user (subset of <see cref="UnexpectedAdminMembers"/>).</summary>
+            public List<string> RoleViolations { get; set; } = new List<string>();
+
+            /// <summary>Per-account state: name, disabled, administrators_member, rid.</summary>
            public List<Dictionary<string, object>> AccountDetails { get; set; } = new List<Dictionary<string, object>>();

            /// <summary>Every Administrators member (DOMAIN\name or SID), local or not — for delta comparison.</summary>
@@ -753,6 +831,38 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Analyzers
            public bool? BuiltInAdministratorEnabled { get; set; }
        }

+        /// <summary>One effective allowed-list entry: a name or glob and what it may allow.</summary>
+        internal sealed class AllowedEntry
+        {
+            public AllowedEntry(string pattern, LocalAccountRole role, bool profileFolderOnly)
+            {
+                Pattern = pattern;
+                Role = role;
+                ProfileFolderOnly = profileFolderOnly;
+            }
+
+            public string Pattern { get; }
+
+            public LocalAccountRole Role { get; }
+
+            /// <summary>Allows the C:\Users folder of this name, never a local account.</summary>
+            public bool ProfileFolderOnly { get; }
+
+            /// <summary>Canonical entry text as the event lists it ("Guest|user").</summary>
+            public string Display => LocalAdminAllowList.Format(Pattern, Role);
+        }
+
+        internal enum AccountDecision
+        {
+            Allowed,
+
+            /// <summary>No entry allows the account.</summary>
+            Unlisted,
+
+            /// <summary>An administrator that a standard-user entry (or a built-in RID) allows only as a standard user.</summary>
+            RoleViolation,
+        }
+
        /// <summary>Logged-in users at shutdown, split by whether the name is a local SAM account.</summary>
        internal sealed class LoggedInUserSplit
        {
@@ -11,6 +11,7 @@ using AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals;
 using AutopilotMonitor.Agent.V2.Core.Monitoring.Interop;
 using AutopilotMonitor.Agent.V2.Core.Orchestration;
 using AutopilotMonitor.Agent.V2.Core.Security;
+using AutopilotMonitor.Agent.V2.Core.Transport;
 using AutopilotMonitor.DecisionCore.Engine;
 using AutopilotMonitor.DecisionCore.Signals;
 using AutopilotMonitor.Shared;
@@ -113,34 +114,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.DeviceInfo
        {
            try
            {
-                var data = new Dictionary<string, object>();
-
-                using (var key = Registry.CurrentUser.OpenSubKey(@"Software\Microsoft\Windows\CurrentVersion\Internet Settings"))
-                {
-                    if (key != null)
-                    {
-                        data["proxyEnabled"] = key.GetValue("ProxyEnable")?.ToString() == "1";
-                        data["proxyServer"] = key.GetValue("ProxyServer")?.ToString();
-                        data["proxyOverride"] = key.GetValue("ProxyOverride")?.ToString();
-                        data["autoConfigUrl"] = key.GetValue("AutoConfigURL")?.ToString();
-                    }
-                }
-
-                // Also check WinHTTP proxy
-                using (var key = Registry.LocalMachine.OpenSubKey(@"SOFTWARE\Microsoft\Windows\CurrentVersion\Internet Settings\Connections"))
-                {
-                    data["winHttpProxyConfigured"] = key?.GetValue("WinHttpSettings") != null;
-                }
-
-                var proxyType = "Direct";
-                if (data.ContainsKey("proxyEnabled") && (bool)data["proxyEnabled"])
-                    proxyType = "Proxy";
-                else if (data.ContainsKey("autoConfigUrl") && data["autoConfigUrl"] != null)
-                    proxyType = "PAC";
-
-                data["proxyType"] = proxyType;
-
-                EmitDeviceInfoEvent(Constants.EventTypes.ProxyConfiguration, $"Proxy configuration: {proxyType}", data);
+                var settings = ProxySettingsReader.Read();
+                EmitDeviceInfoEvent(Constants.EventTypes.ProxyConfiguration, $"Proxy configuration: {settings.ProxyType}", settings.ToEventData());
            }
            catch (Exception ex)
            {
@@ -1004,7 +979,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.DeviceInfo
            var fingerprint = Persistence.StartupEventGate.ComputeFingerprint(data, excludedFields);
            if (_startupGate.ShouldEmit(eventType, fingerprint)) return true;

-            _logger.Debug($"EnrollmentTracker: '{eventType}' suppressed — payload unchanged since last emission (restart dedup)");
+            _logger.Debug($"EnrollmentTracker: '{eventType}' suppressed — payload unchanged since last emission (restart dedup)", repeatKey: "DeviceInfo.unchanged:" + eventType);
            return false;
        }

@@ -79,11 +79,14 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Office

        public void Start()
        {
+            bool raise;
            lock (_lock)
            {
                if (_disposed) return;
-                TryArm();
+                raise = TryArm();
            }
+
+            if (raise) Raise();
        }

        /// <summary>
@@ -129,17 +132,14 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Office
            }
        }

-        // Caller holds _lock.
-        private void TryArm()
+        // Caller holds _lock. Returns true when BinaryAppeared is due; the caller raises it after
+        // releasing the lock, like OnRecheck does — the handler probes and may dispose this watcher.
+        private bool TryArm()
        {
-            if (_disposed || _fsw != null) return;
+            if (_disposed || _fsw != null) return false;

            // Initial scan — the binaries may already be present (armed late / update over existing).
-            if (CoreBinariesPresent())
-            {
-                Raise();
-                return;
-            }
+            if (CoreBinariesPresent()) return true;

            if (!Directory.Exists(_installationPath))
            {
@@ -154,7 +154,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Office
                {
                    _logger.Debug($"[OfficeBinaryWatcher] install path '{_installationPath}' never appeared — giving up (no completion proof)");
                }
-                return;
+                return false;
            }

            try
@@ -172,17 +172,21 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Office
                _logger.Info($"[OfficeBinaryWatcher] watching '{_installationPath}' for core Office binaries");

                // Race: a binary may have appeared between the scan above and arming — re-scan once.
-                if (CoreBinariesPresent()) Raise();
+                return CoreBinariesPresent();
            }
            catch (Exception ex)
            {
                _logger.Warning($"[OfficeBinaryWatcher] could not watch '{_installationPath}': {ex.Message}");
+                return false;
            }
        }

        private void OnArmRetry(object? state)
        {
-            lock (_lock) { TryArm(); }
+            bool raise;
+            lock (_lock) { raise = TryArm(); }
+
+            if (raise) Raise();
        }

        private void OnFileEvent(object sender, FileSystemEventArgs e) => CheckCandidate(e.Name);
@@ -4,6 +4,7 @@ using System.Collections.Generic;
 using System.Diagnostics;
 using System.Management;
 using System.Threading;
+using System.Threading.Tasks;
 using AutopilotMonitor.Agent.V2.Core.Logging;

 namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Office
@@ -15,7 +16,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Office
    /// idle polling:
    /// <list type="bullet">
    ///   <item><b>Start</b> — a true ETW-backed push via WMI <c>Win32_ProcessStartTrace</c>
-    ///     (<see cref="ManagementEventWatcher"/>), plus a one-shot startup probe so an install already
+    ///     (<see cref="ManagementEventWatcher"/>), plus a startup probe so an install already
    ///     in flight when the agent boots (realistic during OOBE) is still caught.</item>
    ///   <item><b>Stop</b> — <see cref="Process.Exited"/> on each tracked worker (clean OS event, same
    ///     pattern as <c>ImeProcessWatcher</c>).</item>
@@ -26,6 +27,12 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Office
    /// a single active window). Fail-soft: if the WMI watcher cannot start, it is logged and the
    /// startup probe still covers the already-running case — no polling fallback by design.
    /// </para>
+    /// <para>
+    /// <b>Locking</b>: the lock guards this watcher's own state. No event is raised and no
+    /// <see cref="Process"/> is disposed while it is held: .NET holds its own lock on a
+    /// <see cref="Process"/> for as long as it delivers <see cref="Process.Exited"/>, that handler
+    /// takes this lock, and <see cref="Process.Dispose()"/> waits for the delivery to finish.
+    /// </para>
    /// </summary>
    public sealed class OfficeProcessWatcher : IDisposable
    {
@@ -53,6 +60,9 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Office
        /// </summary>
        public event EventHandler? Stopped;

+        /// <summary>Test seam: enumerates the running workers (default: Process.GetProcessesByName).</summary>
+        internal Func<Process[]> WorkerSource { get; set; } = () => Process.GetProcessesByName(WorkerProcessNameNoExt);
+
        /// <param name="settleSeconds">Grace period after the last worker exits before the window is
        /// declared closed; a new worker within it keeps the window open. &lt;=0 closes immediately.</param>
        public OfficeProcessWatcher(AgentLogger logger, int settleSeconds = 10)
@@ -67,7 +77,10 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Office
            get { lock (_lock) { return _active; } }
        }

-        public void Start()
+        public void Start() => Start(armWmi: true);
+
+        /// <summary>Test seam: <paramref name="armWmi"/> = false leaves out the WMI subscription.</summary>
+        internal void Start(bool armWmi)
        {
            lock (_lock)
            {
@@ -75,10 +88,22 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Office
                _started = true;
            }

-            // 1) Startup probe — catch a worker already running before the watcher armed.
+            // 1) Startup probe — catch a worker already running before the subscription exists. It
+            //    stays on the caller's thread: it needs no WMI, so a worker that is already running is
+            //    reported even when the subscription below never completes.
+            ProbeRunningWorkers();
+
+            // 2) ETW-backed push on worker creation — no polling. WinMgmt can hang during OOBE, so the
+            //    subscription never runs on the caller's thread (the orchestrator starts its hosts one
+            //    after another on it).
+            if (armWmi) Task.Run(() => ArmStartTrace());
+        }
+
+        private void ProbeRunningWorkers()
+        {
            try
            {
-                foreach (var proc in Process.GetProcessesByName(WorkerProcessNameNoExt))
+                foreach (var proc in WorkerSource())
                {
                    TrackWorker(proc);
                }
@@ -87,24 +112,52 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Office
            {
                _logger.Warning($"[OfficeProcessWatcher] startup probe failed: {ex.Message}");
            }
+        }

-            // 2) ETW-backed push on worker creation — no polling.
+        private void ArmStartTrace()
+        {
+            ManagementEventWatcher? watcher = null;
            try
            {
-                var query = new WqlEventQuery(
-                    $"SELECT * FROM Win32_ProcessStartTrace WHERE ProcessName = '{WorkerProcessName}'");
-                _startWatcher = new ManagementEventWatcher(query);
-                _startWatcher.EventArrived += OnProcessStartTrace;
-                _startWatcher.Start();
-                _logger.Info($"[OfficeProcessWatcher] watching Win32_ProcessStartTrace for {WorkerProcessName}");
+                watcher = new ManagementEventWatcher(new WqlEventQuery(
+                    $"SELECT * FROM Win32_ProcessStartTrace WHERE ProcessName = '{WorkerProcessName}'"));
+                watcher.EventArrived += OnProcessStartTrace;
+                watcher.Start();
            }
            catch (Exception ex)
            {
                // No polling fallback by design — the startup probe already covers the in-flight case.
                _logger.Warning($"[OfficeProcessWatcher] could not start WMI process-start watcher " +
                    $"({ex.GetType().Name}: {ex.Message}); relying on the startup probe only.");
-                _startWatcher = null;
+                if (watcher != null) TearDownStartTrace(watcher);
+                return;
            }
+
+            // Published only once it is armed, so Dispose never meets a half-started subscription; one
+            // that completes after Dispose is taken down right here.
+            bool keep;
+            lock (_lock)
+            {
+                keep = !_disposed;
+                if (keep) _startWatcher = watcher;
+            }
+            if (!keep)
+            {
+                TearDownStartTrace(watcher);
+                return;
+            }
+
+            _logger.Info($"[OfficeProcessWatcher] watching Win32_ProcessStartTrace for {WorkerProcessName}");
+
+            // A worker may have started between the probe in Start and the subscription.
+            ProbeRunningWorkers();
+        }
+
+        private void TearDownStartTrace(ManagementEventWatcher watcher)
+        {
+            try { watcher.EventArrived -= OnProcessStartTrace; } catch { }
+            try { watcher.Stop(); } catch { }
+            try { watcher.Dispose(); } catch { }
        }

        private void OnProcessStartTrace(object sender, EventArrivedEventArgs e)
@@ -128,39 +181,48 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Office

        private void TrackWorker(Process proc)
        {
+            bool tracked = false;
            bool raiseStarted = false;
            try
            {
                lock (_lock)
                {
-                    if (_disposed) { try { proc.Dispose(); } catch { } return; }
-                    if (_workers.ContainsKey(proc.Id)) { try { proc.Dispose(); } catch { } return; }
+                    if (!_disposed && !_workers.ContainsKey(proc.Id))
+                    {
+                        try
+                        {
+                            proc.EnableRaisingEvents = true;
+                            proc.Exited += OnWorkerExited;
+                            tracked = true;
+                        }
+                        catch
+                        {
+                            // Process exited between discovery and Exited-hookup — drop it.
+                        }

-                    try
-                    {
-                        proc.EnableRaisingEvents = true;
-                        proc.Exited += OnWorkerExited;
-                    }
-                    catch
-                    {
-                        // Process exited between discovery and Exited-hookup — drop it.
-                        try { proc.Dispose(); } catch { }
-                        return;
-                    }
-
-                    _workers[proc.Id] = proc;
-                    // A worker is back — cancel any pending settle (the window must stay open).
-                    CancelSettleTimer();
-                    if (!_active)
-                    {
-                        _active = true;
-                        raiseStarted = true;
+                        if (tracked)
+                        {
+                            _workers[proc.Id] = proc;
+                            // A worker is back — cancel any pending settle (the window must stay open).
+                            CancelSettleTimer();
+                            if (!_active)
+                            {
+                                _active = true;
+                                raiseStarted = true;
+                            }
+                        }
                    }
                }
            }
            catch (Exception ex)
            {
                _logger.Debug($"[OfficeProcessWatcher] TrackWorker error: {ex.Message}");
+            }
+
+            if (!tracked)
+            {
+                // Disposed, already tracked under another handle, or gone before the hookup.
+                try { proc.Dispose(); } catch { }
                return;
            }

@@ -169,6 +231,11 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Office
                _logger.Info($"[OfficeProcessWatcher] Office worker started (PID={SafePid(proc)}) — install active");
                RaiseStarted();
            }
+
+            // .NET raises Exited once per Process object. A worker that exited before the hookup
+            // above was subscribed would stay tracked forever and the window would never close.
+            if (HasExitedSafe(proc))
+                ThreadPool.QueueUserWorkItem(_ => OnWorkerExited(proc, EventArgs.Empty));
        }

        private void OnWorkerExited(object? sender, EventArgs e)
@@ -178,11 +245,12 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Office

            lock (_lock)
            {
-                if (_workers.Remove(SafePid(proc)))
-                {
-                    try { proc.Exited -= OnWorkerExited; } catch { }
-                    try { proc.Dispose(); } catch { }
-                }
+                // Only the call that still finds this worker acts: after Dispose nothing is tracked,
+                // and TrackWorker's own re-check can deliver the same exit a second time.
+                if (_disposed || !_workers.TryGetValue(SafePid(proc), out var tracked) || !ReferenceEquals(tracked, proc))
+                    return;
+                _workers.Remove(SafePid(proc));
+
                if (_active && _workers.Count == 0)
                {
                    if (_settleSeconds <= 0)
@@ -200,6 +268,9 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Office
                }
            }

+            try { proc.Exited -= OnWorkerExited; } catch { }
+            try { proc.Dispose(); } catch { }
+
            if (raiseStoppedNow)
            {
                _logger.Info("[OfficeProcessWatcher] last Office worker exited — install window closed");
@@ -260,31 +331,40 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Office
            try { return proc.Id; } catch { return -1; }
        }

+        private static bool HasExitedSafe(Process proc)
+        {
+            try { return proc.HasExited; } catch { return false; }
+        }
+
        public void Dispose()
        {
+            ManagementEventWatcher? startWatcher;
+            Process[] workers;
            lock (_lock)
            {
                if (_disposed) return;
                _disposed = true;
-            }

-            if (_startWatcher != null)
-            {
-                try { _startWatcher.EventArrived -= OnProcessStartTrace; } catch { }
-                try { _startWatcher.Stop(); } catch { }
-                try { _startWatcher.Dispose(); } catch { }
+                startWatcher = _startWatcher;
                _startWatcher = null;
+                CancelSettleTimer();
+                workers = new Process[_workers.Count];
+                _workers.Values.CopyTo(workers, 0);
+                _workers.Clear();
            }

-            lock (_lock)
+            if (startWatcher != null)
            {
-                CancelSettleTimer();
-                foreach (var kv in _workers)
-                {
-                    try { kv.Value.Exited -= OnWorkerExited; } catch { }
-                    try { kv.Value.Dispose(); } catch { }
-                }
-                _workers.Clear();
+                // Cancelling a WMI subscription can take tens of seconds on a busy WinMgmt. The caller
+                // is the agent's stop path, so it never waits for it.
+                var armed = startWatcher;
+                Task.Run(() => TearDownStartTrace(armed));
+            }
+
+            foreach (var worker in workers)
+            {
+                try { worker.Exited -= OnWorkerExited; } catch { }
+                try { worker.Dispose(); } catch { }
            }
        }
    }
@@ -26,6 +26,12 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Office
    /// </para>
    /// One-shot per OS contract, so it re-arms after each fire. Fail-soft: any failure is logged and
    /// the watcher stays quiet (the detector still gets the process Started/Stopped boundary events).
+    /// <para>
+    /// <b>Locking</b>: the lock guards this watcher's own state and is never held while
+    /// <see cref="Changed"/> is raised. A handler may dispose the watcher or take locks of its own,
+    /// and <see cref="Dispose"/> never waits for a handler. Raising under the lock deadlocks against
+    /// an owner that disposes this watcher under a lock its handler also takes.
+    /// </para>
    /// </summary>
    public sealed class RegistryChangeWatcher : IDisposable
    {
@@ -34,10 +40,16 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Office
        {
            ChangeName = 0x00000001,      // subkey added/removed (ClickToRun appearing; Scenario\* churn)
            ChangeLastSet = 0x00000004,   // value set (Configuration: VersionToReport / StreamingFinished)
+            // The registration must outlive the thread that issued it: re-arming happens on rotating
+            // ThreadPool threads, and without this flag Windows signals the event when such a thread
+            // ends — reported here as a change that never happened.
+            ThreadAgnostic = 0x10000000,
        }

-        private const RegNotifyFilter PrimaryFilter = RegNotifyFilter.ChangeName | RegNotifyFilter.ChangeLastSet;
-        private const RegNotifyFilter BootstrapFilter = RegNotifyFilter.ChangeName; // cheap: direct-child create/delete only
+        private const RegNotifyFilter PrimaryFilter =
+            RegNotifyFilter.ChangeName | RegNotifyFilter.ChangeLastSet | RegNotifyFilter.ThreadAgnostic;
+        // Cheap: direct-child create/delete only.
+        private const RegNotifyFilter BootstrapFilter = RegNotifyFilter.ChangeName | RegNotifyFilter.ThreadAgnostic;

        [DllImport("advapi32.dll", SetLastError = true)]
        private static extern int RegNotifyChangeKeyValue(
@@ -49,6 +61,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Office

        private enum WatchMode { None, Primary, Bootstrap }

+        private readonly RegistryHive _hive;
+        private readonly string _hiveLabel;
        private readonly string _targetSubKey;
        private readonly AgentLogger _logger;
        private readonly object _lock = new object();
@@ -66,13 +80,25 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Office

        /// <param name="targetSubKey">HKLM-relative key, e.g. <c>SOFTWARE\Microsoft\Office\ClickToRun</c>.</param>
        public RegistryChangeWatcher(string targetSubKey, AgentLogger logger)
+            : this(RegistryHive.LocalMachine, targetSubKey, logger)
        {
+        }
+
+        /// <summary>Test seam: production always watches HKLM; tests use a hive they may write to.</summary>
+        internal RegistryChangeWatcher(RegistryHive hive, string targetSubKey, AgentLogger logger)
+        {
+            _hive = hive;
+            _hiveLabel = hive == RegistryHive.LocalMachine ? "HKLM" : hive.ToString();
            _targetSubKey = targetSubKey ?? throw new ArgumentNullException(nameof(targetSubKey));
            _logger = logger ?? throw new ArgumentNullException(nameof(logger));
        }

+        /// <summary>The filter the full target watch is armed with (tests).</summary>
+        internal uint EffectivePrimaryFilter => (uint)PrimaryFilter;
+
        public void Start()
        {
+            bool raise = false;
            lock (_lock)
            {
                if (_started || _disposed) return;
@@ -81,24 +107,30 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Office
                {
                    // Forced Registry64 view — consistent with the C2R reads (AnyCPU net48 may otherwise
                    // resolve the stale WOW6432Node mirror).
-                    _baseKey = RegistryKey.OpenBaseKey(RegistryHive.LocalMachine, RegistryView.Registry64);
+                    _baseKey = RegistryKey.OpenBaseKey(_hive, RegistryView.Registry64);
                    _signal = new AutoResetEvent(false);
-                    ArmBestEffort(raiseOnPromote: false);
+                    raise = ArmBestEffort(targetIsNews: false);
                }
                catch (Exception ex)
                {
-                    _logger.Warning($"[RegistryChangeWatcher] failed to start on HKLM\\{_targetSubKey}: {ex.Message}");
+                    _logger.Warning($"[RegistryChangeWatcher] failed to start on {_hiveLabel}\\{_targetSubKey}: {ex.Message}");
                }
            }
+
+            if (raise) RaiseChanged();
        }

        /// <summary>
        /// Arms the best available watch: the target key (full, subtree) if it exists, otherwise a cheap
        /// name-only watch on the nearest existing ancestor until the target appears. Must hold <see cref="_lock"/>.
+        /// Returns true when the target key appeared and the caller has to raise <see cref="Changed"/>
+        /// for it — after releasing the lock.
        /// </summary>
-        private void ArmBestEffort(bool raiseOnPromote)
+        /// <param name="targetIsNews">False when finding the target right away is the expected start
+        /// state; true when the watch was waiting for it.</param>
+        private bool ArmBestEffort(bool targetIsNews)
        {
-            if (_disposed || _baseKey == null) return;
+            if (_disposed || _baseKey == null) return false;

            CloseWatchedKey();

@@ -107,27 +139,25 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Office
            {
                _watchedKey = target;
                _mode = WatchMode.Primary;
-                if (!ArmNotify(subtree: true, PrimaryFilter)) return;
-                if (raiseOnPromote) RaiseChanged();
-                return;
+                return ArmNotify(subtree: true, PrimaryFilter) && targetIsNews;
            }

            // Target absent — watch the nearest existing ancestor (non-recursive, name-only = cheap).
            var ancestor = OpenNearestExistingAncestor(out var ancestorPath);
            if (ancestor == null)
            {
-                _logger.Debug($"[RegistryChangeWatcher] no existing ancestor for HKLM\\{_targetSubKey}; not arming");
-                return;
+                _logger.Debug($"[RegistryChangeWatcher] no existing ancestor for {_hiveLabel}\\{_targetSubKey}; not arming");
+                return false;
            }
            _watchedKey = ancestor;
            _mode = WatchMode.Bootstrap;
-            _logger.Debug($"[RegistryChangeWatcher] target HKLM\\{_targetSubKey} absent — bootstrap-watching HKLM\\{ancestorPath} (name-only)", repeatKey: "RegistryChangeWatcher.bootstrap:" + _targetSubKey);
-            if (!ArmNotify(subtree: false, BootstrapFilter)) return;
+            _logger.Debug($"[RegistryChangeWatcher] target {_hiveLabel}\\{_targetSubKey} absent — bootstrap-watching {_hiveLabel}\\{ancestorPath} (name-only)", repeatKey: "RegistryChangeWatcher.bootstrap:" + _targetSubKey);
+            if (!ArmNotify(subtree: false, BootstrapFilter)) return false;

            // TOCTOU: the target may have been created between TryOpen and arming the ancestor watch.
            using (var recheck = TryOpen(_targetSubKey))
            {
-                if (recheck != null) ArmBestEffort(raiseOnPromote: true);
+                return recheck != null && ArmBestEffort(targetIsNews: true);
            }
        }

@@ -139,7 +169,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Office
                int rc = RegNotifyChangeKeyValue(_watchedKey.Handle, subtree, filter, _signal.SafeWaitHandle, fAsynchronous: true);
                if (rc != 0)
                {
-                    _logger.Warning($"[RegistryChangeWatcher] RegNotifyChangeKeyValue failed rc={rc} (HKLM\\{_targetSubKey})");
+                    _logger.Warning($"[RegistryChangeWatcher] RegNotifyChangeKeyValue failed rc={rc} ({_hiveLabel}\\{_targetSubKey})");
                    return false;
                }
                UnregisterWait();
@@ -149,29 +179,35 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Office
            }
            catch (Exception ex)
            {
-                _logger.Warning($"[RegistryChangeWatcher] arm failed (HKLM\\{_targetSubKey}): {ex.Message}");
+                _logger.Warning($"[RegistryChangeWatcher] arm failed ({_hiveLabel}\\{_targetSubKey}): {ex.Message}");
                return false;
            }
        }

        private void OnSignalled(object? state, bool timedOut)
        {
+            bool raise;
+            bool rearmAfterHandler;
            lock (_lock)
            {
                UnregisterWait();
                if (_disposed || timedOut) return;

-                if (_mode == WatchMode.Primary)
-                {
-                    RaiseChanged();
-                    ArmNotify(subtree: true, PrimaryFilter); // re-arm on the same target key
-                }
-                else
-                {
-                    // A direct child changed under the ancestor — promote to the target watch if it now
-                    // exists (raises Changed on promotion), else keep the cheap bootstrap watch.
-                    ArmBestEffort(raiseOnPromote: true);
-                }
+                rearmAfterHandler = _mode == WatchMode.Primary;
+                // Bootstrap: a direct child changed under the ancestor — promote to the target watch if
+                // it now exists (then Changed is due), else keep the cheap bootstrap watch.
+                raise = rearmAfterHandler || ArmBestEffort(targetIsNews: true);
+            }
+
+            if (raise) RaiseChanged();
+
+            if (!rearmAfterHandler) return;
+            lock (_lock)
+            {
+                // Re-arm on the same target key, and only now: no wait was registered while the handler
+                // ran, so handlers never overlap, and a change that arrived meanwhile completes this
+                // registration at once.
+                ArmNotify(subtree: true, PrimaryFilter);
            }
        }

@@ -200,6 +236,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Office
            }
        }

+        // Never called with _lock held.
        private void RaiseChanged()
        {
            var handler = Changed;
@@ -160,6 +160,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Periodic
            // Suppress events when network hasn't actually changed (DHCP renewals, OS chatter)
            if (previousState != null && previousState.IsSameNetwork(newState))
            {
+                // Every occurrence on purpose, no repeatKey: when it happened is the information
+                // (did anything move on the network when uploads stopped?).
                _logger.Debug("NetworkChangeDetector: network address changed but same logical network — suppressing");
                return;
            }
@@ -260,6 +260,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Transport
                {
                    await ThrowOnAuthFailureAsync(response, correlationId).ConfigureAwait(false);
                    await ThrowOnCodedConflictAsync(response).ConfigureAwait(false);
+                    ThrowOnSessionGone(response, correlationId);
                    response.EnsureSuccessStatusCode();

                    var responseJson = await response.Content.ReadAsStringAsync().ConfigureAwait(false);
@@ -412,6 +413,24 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Transport
                errorCode);
        }

+        /// <summary>
+        /// Throws <see cref="BackendSessionGoneException"/> for a 410 the backend answered: the
+        /// session was deleted or is being deleted. Only a response that echoes this request's
+        /// <c>X-Correlation-ID</c> counts — the caller ends monitoring on it, so a 410 from the
+        /// network path stays an ordinary failure (<c>EnsureSuccessStatusCode</c>) and is retried.
+        /// </summary>
+        private static void ThrowOnSessionGone(HttpResponseMessage response, string correlationId)
+        {
+            if (response.StatusCode != HttpStatusCode.Gone)
+                return;
+            if (!ResponseOriginClassifier.EchoesCorrelationId(response, correlationId))
+                return;
+
+            throw new BackendSessionGoneException(
+                "Backend returned 410 Gone: the session was deleted or is being deleted.",
+                (int)response.StatusCode);
+        }
+
        /// <summary>
        /// Pulls <c>errorCode</c> out of a backend JSON error body. Tolerant: any parse failure
        /// or a non-string value yields null, never an exception.
@@ -537,4 +556,19 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Transport
            ErrorCode = errorCode;
        }
    }
+
+    /// <summary>
+    /// Thrown for a 410 Gone the backend answered: the session named in the request was deleted or
+    /// is being deleted. No retry can clear it and it says nothing about the device's authorization.
+    /// </summary>
+    public class BackendSessionGoneException : Exception
+    {
+        /// <summary>HTTP status code returned by the backend (410).</summary>
+        public int StatusCode { get; }
+
+        public BackendSessionGoneException(string message, int statusCode) : base(message)
+        {
+            StatusCode = statusCode;
+        }
+    }
 }
@@ -194,7 +194,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Transport
            catch (Exception ex)
            {
                // Swallow — distress channel must never cascade failures into the caller
-                _logger?.Debug($"[DistressChannel] Failed to send report: {ex.Message}");
+                _logger?.Debug($"[DistressChannel] Failed to send report: {TransportErrorCodes.DescribeSendFailure(ex)}");
            }
        }

@@ -15,7 +15,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Transport
    ///   - Same error key (ErrorType + HTTP status code) is only ever sent once per session
    ///   - At most <see cref="MaxReportsPerSession"/> emergency reports total per session
    ///   - At most one report every <see cref="MinIntervalMinutes"/> minutes regardless of error type
-    ///     (the terminal <see cref="AgentErrorType.TelemetryRejectedSessionUnknown"/> report is exempt)
+    ///     (the terminal session-gone reports <see cref="AgentErrorType.TelemetryRejectedSessionUnknown"/>
+    ///     and <see cref="AgentErrorType.RegistrationRejectedSessionGone"/> are exempt)
    ///
    /// A failure in this reporter is silently swallowed — it must never cascade into the main loop.
    /// </summary>
@@ -123,11 +124,12 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Transport
                    return;
                }

-                // The session-unknown report is terminal and sent at most once per process (the
+                // A session-gone report is terminal and sent at most once per process (the
                // termination follows immediately): a routine report minutes earlier must not cost
                // the last word about the session. Only the cooldown is waived; key dedup and the
                // per-session maximum still apply.
-                var exemptFromCooldown = errorType == AgentErrorType.TelemetryRejectedSessionUnknown;
+                var exemptFromCooldown = errorType == AgentErrorType.TelemetryRejectedSessionUnknown
+                    || errorType == AgentErrorType.RegistrationRejectedSessionGone;
                if (!exemptFromCooldown && _lastReportTime != null &&
                    (now - _lastReportTime.Value).TotalMinutes < MinIntervalMinutes)
                {
@@ -180,7 +182,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Transport
            catch (Exception ex)
            {
                // Swallow — emergency channel must never cascade failures into the caller
-                _logger?.Debug($"[EmergencyChannel] Failed to send report: {ex.Message}");
+                _logger?.Debug($"[EmergencyChannel] Failed to send report: {TransportErrorCodes.DescribeSendFailure(ex)}");
            }

            if (!delivered)
@@ -1,6 +1,8 @@
 using System;
 using System.ComponentModel;
 using System.Globalization;
+using System.Net;
+using System.Net.Sockets;

 namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Transport
 {
@@ -31,6 +33,38 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Transport
            return code == null ? ex.Message : $"{ex.Message} (win32 {code})";
        }

+        /// <summary>
+        /// What a failed send hit, in one line: the <see cref="WebException.Status"/>, the socket error
+        /// or native code, and the innermost message. On .NET Framework a socket error's message names
+        /// the endpoint it tried, which tells a backend that does not answer from a proxy that does not.
+        /// </summary>
+        public static string DescribeSendFailure(Exception ex)
+        {
+            if (ex == null) return null;
+
+            WebExceptionStatus? status = null;
+            SocketError? socketError = null;
+            var innermost = ex;
+            for (var current = ex; current != null; current = current.InnerException)
+            {
+                innermost = current;
+                if (current is WebException web && status == null) status = web.Status;
+                if (current is SocketException socket) socketError = socket.SocketErrorCode;
+            }
+
+            var code = socketError.HasValue ? $"socket={socketError.Value}" : NativeCodePart(ex);
+            var details = status.HasValue
+                ? (code == null ? $"status={status.Value}" : $"status={status.Value}, {code}")
+                : code;
+            return details == null ? innermost.Message : $"{details}: {innermost.Message}";
+        }
+
+        private static string NativeCodePart(Exception ex)
+        {
+            var code = InnermostNativeCode(ex);
+            return code == null ? null : $"win32={code}";
+        }
+
        /// <summary>Eight-digit hex with <c>0x</c>: <c>-2146893018</c> → <c>0x80090326</c>.</summary>
        public static string Hex(int value) => "0x" + value.ToString("X8", CultureInfo.InvariantCulture);
    }
@@ -96,6 +96,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
        /// </summary>
        private readonly DateTime? _previousRunLastAliveUtc;

+        private readonly Transport.ProxyObserver? _proxyObserver;
+
        public DefaultComponentFactory(
            AgentConfiguration agentConfig,
            AgentConfigResponse remoteConfig,
@@ -105,7 +107,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
            Persistence.StartupEventGate? startupEventGate = null,
            DateTime? previousBootUtc = null,
            string? previousExitType = null,
-            DateTime? previousRunLastAliveUtc = null)
+            DateTime? previousRunLastAliveUtc = null,
+            Transport.ProxyObserver? proxyObserver = null)
        {
            _agentConfig = agentConfig ?? throw new ArgumentNullException(nameof(agentConfig));
            _remoteConfig = remoteConfig ?? throw new ArgumentNullException(nameof(remoteConfig));
@@ -116,6 +119,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
            _previousBootUtc = previousBootUtc;
            _previousExitType = previousExitType;
            _previousRunLastAliveUtc = previousRunLastAliveUtc;
+            _proxyObserver = proxyObserver;
        }

        /// <summary>
@@ -352,28 +356,16 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
            hosts.Add(aadJoinHost);
            aadJoinHostRef = aadJoinHost;

-            // RealmJoin support is opt-in per tenant (portal toggle → AnalyzerConfiguration.
-            // EnableRealmJoinWatcher, default off). When disabled, leave realmJoinHost null:
-            // the DesktopArrival observer above already null-guards it, so the HKU watcher is
-            // never armed and no RealmJoin signals are produced. The compile-time const
-            // RealmJoinHost.RealmJoinTrackingEnabled remains a build-time master kill-switch;
-            // the effective enable is (remote flag AND const).
            var analyzers = _remoteConfig.Analyzers ?? new AnalyzerConfiguration();
-            if (analyzers.EnableRealmJoinWatcher && RealmJoinHost.RealmJoinTrackingEnabled)
-            {
-                realmJoinHost = new RealmJoinHost(logger, ingress, clock);
-                hosts.Add(realmJoinHost);
-            }
-            else
-            {
-                logger.Info($"DefaultComponentFactory: RealmJoinHost not created (EnableRealmJoinWatcher={analyzers.EnableRealmJoinWatcher}, RealmJoinTrackingEnabled={RealmJoinHost.RealmJoinTrackingEnabled})");
-            }

            // Keep-awake during User-ESP — opt-in per tenant (portal toggle → AnalyzerConfiguration.
            // KeepAwakeDuringUserEsp, default off). The host observes the signal rail and holds the
-            // device awake (system + display) from AccountSetup entry until provisioning completes
-            // (or a safety cap), so idle standby cannot stall app installs / account setup. Reboots
+            // device awake (system + display) from AccountSetup entry until the user-ESP page
+            // closes — with the RealmJoin Watcher on, until RealmJoin starts its deployment (D-413) —
+            // or a safety cap, so idle standby cannot stall app installs / account setup. Reboots
            // are unaffected; the OS auto-clears the hold on process exit.
+            // ORDER: before the RealmJoinHost — after an agent restart the watcher posts
+            // realmjoin_detected from its own Start, and this host must already be subscribed.
            if (analyzers.KeepAwakeDuringUserEsp)
            {
                hosts.Add(new UserEspKeepAwakeHost(
@@ -382,7 +374,25 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
                    logger: logger,
                    // q8n: release on the user-ESP page exit, i.e. a Shell-Core 62407 that arrives
                    // after the AccountSetup registry left notStarted — never on the handoff exit.
-                    accountSetupProgressProbe: () => espAndHelloHost.HasAccountSetupProgress));
+                    accountSetupProgressProbe: () => espAndHelloHost.HasAccountSetupProgress,
+                    // D-414: that exit is latched here, so a later agent run does not engage again.
+                    startupGate: _startupEventGate));
+            }
+
+            // RealmJoin support is opt-in per tenant (portal toggle → AnalyzerConfiguration.
+            // EnableRealmJoinWatcher, default off). When disabled, leave realmJoinHost null:
+            // the DesktopArrival observer above already null-guards it, so the HKU watcher is
+            // never armed and no RealmJoin signals are produced. The compile-time const
+            // RealmJoinHost.RealmJoinTrackingEnabled remains a build-time master kill-switch;
+            // the effective enable is (remote flag AND const).
+            if (analyzers.EnableRealmJoinWatcher && RealmJoinHost.RealmJoinTrackingEnabled)
+            {
+                realmJoinHost = new RealmJoinHost(logger, ingress, clock);
+                hosts.Add(realmJoinHost);
+            }
+            else
+            {
+                logger.Info($"DefaultComponentFactory: RealmJoinHost not created (EnableRealmJoinWatcher={analyzers.EnableRealmJoinWatcher}, RealmJoinTrackingEnabled={RealmJoinHost.RealmJoinTrackingEnabled})");
            }

            // OOBE-console / Shift+F10 detection — opt-OUT per tenant (portal toggle →
@@ -666,6 +676,17 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
                clock: clock,
                logger: logger));

+            // The exact time of a proxy change for the agent log and the timeline. Always on: when
+            // this matters, nothing else from the device reaches the backend.
+            if (_proxyObserver != null)
+            {
+                hosts.Add(new ProxySettingsHost(
+                    observer: _proxyObserver,
+                    ingress: ingress,
+                    clock: clock,
+                    logger: logger));
+            }
+
            // Live AC/battery watcher — WMI Win32_PowerManagementEvent push (no polling), emits
            // power_state_change on AC↔battery transitions and 50/30/15 % downward threshold
            // crossings. Deliberately NOT under PeriodicCollectorLifecycleHost: it is push-based
@@ -67,6 +67,13 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
        /// <summary>Default Timeout für den Terminal-Drain beim Stop.</summary>
        public static readonly TimeSpan DefaultTerminalDrainTimeout = TimeSpan.FromSeconds(30);

+        /// <summary>
+        /// How long termination waits for ONE collector host to stop (and later to dispose). A whole
+        /// healthy stop pass takes about 0.2 s and the slowest single host seen in the field 7 s, so
+        /// this only ever ends the wait for a host that hangs.
+        /// </summary>
+        public static readonly TimeSpan DefaultCollectorHostStopTimeout = TimeSpan.FromSeconds(30);
+
        private readonly string _sessionId;
        private readonly string _tenantId;
        private readonly string _stateDirectory;
@@ -81,6 +88,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
        private readonly int _quarantineThreshold;
        private readonly TimeSpan _drainInterval;
        private readonly TimeSpan _terminalDrainTimeout;
+        private readonly TimeSpan _collectorHostStopTimeout;
        private readonly TimeSpan? _agentMaxLifetime;
        private readonly int _uploadBatchSize;

@@ -124,6 +132,9 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
        private SessionTraceOrdinalProvider? _traceCounter;
        private SignalIngress? _ingress;
        private IReadOnlyList<ICollectorHost>? _collectorHosts;
+        // Hosts that did not come back from Stop or Dispose in time. A thread is still inside them,
+        // so nothing calls into them again. Locked on itself.
+        private readonly HashSet<ICollectorHost> _unresponsiveHosts = new HashSet<ICollectorHost>();

        private EventHandler<DeadlineFiredEventArgs>? _deadlineBridge;

@@ -181,7 +192,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
            int uploadBatchSize = 100,
            IDeadlineScheduler? schedulerOverride = null,
            Func<bool>? traceEventsEnabled = null,
-            Func<bool>? espContinueAnywayObservationEnabled = null)
+            Func<bool>? espContinueAnywayObservationEnabled = null,
+            TimeSpan? collectorHostStopTimeout = null)
        {
            if (string.IsNullOrEmpty(sessionId)) throw new ArgumentException("SessionId is mandatory.", nameof(sessionId));
            if (string.IsNullOrEmpty(tenantId)) throw new ArgumentException("TenantId is mandatory.", nameof(tenantId));
@@ -211,6 +223,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
            _quarantineThreshold = quarantineThreshold;
            _drainInterval = drainInterval ?? DefaultDrainInterval;
            _terminalDrainTimeout = terminalDrainTimeout ?? DefaultTerminalDrainTimeout;
+            _collectorHostStopTimeout = collectorHostStopTimeout ?? DefaultCollectorHostStopTimeout;

            if (agentMaxLifetime.HasValue && agentMaxLifetime.Value <= TimeSpan.Zero)
                throw new ArgumentOutOfRangeException(nameof(agentMaxLifetime), "AgentMaxLifetime must be positive when set.");
@@ -947,6 +960,11 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
        /// diagnostics ZIP is built so periodic collectors (PerformanceCollector,
        /// AgentSelfMetricsCollector, …) don't keep emitting <c>performance_snapshot</c> /
        /// <c>agent_metrics_snapshot</c> events while the package is being assembled.
+        /// <para>
+        /// Bounded per host (<see cref="DefaultCollectorHostStopTimeout"/>): a host that hangs is
+        /// left behind and the remaining hosts are still stopped. The diagnostics upload and the
+        /// self-destruct come after this call, so it has to return whatever a collector does.
+        /// </para>
        /// </summary>
        public void StopCollectorHosts()
        {
@@ -955,8 +973,94 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration

            foreach (var host in _collectorHosts)
            {
-                try { host.Stop(); }
-                catch (Exception ex) { _logger.Warning($"EnrollmentOrchestrator: host '{host.Name}' stop failed: {ex.Message}"); }
+                RunHostStepBounded(host, "stop", h => h.Stop());
+            }
+        }
+
+        /// <summary>
+        /// Runs one host's Stop or Dispose on a thread of its own and waits at most
+        /// <see cref="_collectorHostStopTimeout"/> for it.
+        /// </summary>
+        private void RunHostStepBounded(ICollectorHost host, string step, Action<ICollectorHost> action)
+        {
+            lock (_unresponsiveHosts)
+            {
+                if (_unresponsiveHosts.Contains(host)) return;
+            }
+
+            Exception? failure = null;
+            var worker = new Thread(() =>
+            {
+                try { action(host); }
+                catch (Exception ex) { failure = ex; }
+            })
+            {
+                // Not a ThreadPool thread: a host that hangs would keep one for good, and the pool may
+                // be the very thing that is stuck. Background, so it cannot keep the process alive.
+                IsBackground = true,
+                Name = $"CollectorHost.{step}:{host.Name}",
+            };
+            try { worker.Start(); }
+            catch (Exception ex)
+            {
+                _logger.Warning($"EnrollmentOrchestrator: host '{host.Name}' {step} could not be started: {ex.Message}");
+                return;
+            }
+
+            if (worker.Join(_collectorHostStopTimeout))
+            {
+                if (failure == null) return;
+                if (step == "stop")
+                    _logger.Warning($"EnrollmentOrchestrator: host '{host.Name}' stop failed: {failure.Message}");
+                else
+                    _logger.Debug($"EnrollmentOrchestrator: host '{host.Name}' {step} failed: {failure.Message}");
+                return;
+            }
+
+            lock (_unresponsiveHosts)
+            {
+                _unresponsiveHosts.Add(host);
+            }
+            var seconds = (int)Math.Ceiling(_collectorHostStopTimeout.TotalSeconds);
+            _logger.Warning(
+                $"EnrollmentOrchestrator: host '{host.Name}' did not return from {step} within {seconds}s — " +
+                "termination continues without it.");
+            if (step == "stop") EmitCollectorHostStopTimeout(host.Name, seconds);
+        }
+
+        /// <summary>
+        /// One <c>agent_trace</c> per host that hung in Stop, so the fleet can count it. Deliberately
+        /// not <c>collector_degraded</c>: that one says the collector's signals are missing and gates
+        /// analyze rules, while a host that will not stop has missed nothing. (A host that hangs in
+        /// Dispose is logged only — the ingress is already down by then.)
+        /// </summary>
+        private void EmitCollectorHostStopTimeout(string hostName, int timeoutSeconds)
+        {
+            var ingress = _ingress;
+            if (ingress == null) return;
+            try
+            {
+                new InformationalEventPost(ingress, _clock).Emit(new Shared.Models.EnrollmentEvent
+                {
+                    SessionId = _sessionId,
+                    TenantId = _tenantId,
+                    EventType = Constants.EventTypes.AgentTrace,
+                    Severity = Shared.Models.EventSeverity.Warning,
+                    Source = "EnrollmentOrchestrator",
+                    Phase = Shared.Models.EnrollmentPhase.Unknown,
+                    Message = $"Collector host '{hostName}' did not stop within {timeoutSeconds}s; termination continued without it.",
+                    Timestamp = _clock.UtcNow,
+                    Data = new Dictionary<string, object>(StringComparer.Ordinal)
+                    {
+                        ["decision"] = "collector_host_stop_timeout",
+                        ["host"] = hostName,
+                        ["timeoutSeconds"] = timeoutSeconds,
+                    },
+                });
+            }
+            catch (Exception ex)
+            {
+                _logger.Debug($"EnrollmentOrchestrator: failed to post collector_host_stop_timeout: {ex.Message}");
            }
        }

@@ -1043,12 +1147,13 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
            }
            catch (Exception ex) { _logger.Warning($"EnrollmentOrchestrator: final snapshot save failed: {ex.Message}"); }

-            // 7) Dispose aller Disposables.
+            // 7) Dispose all disposables. Hosts go through the same bound as in StopCollectorHosts;
+            //    one that is still stuck in Stop is skipped (its Dispose would wait on the same thing).
            if (_collectorHosts != null)
            {
                foreach (var host in _collectorHosts)
                {
-                    try { host.Dispose(); } catch { /* best-effort */ }
+                    RunHostStepBounded(host, "dispose", h => h.Dispose());
                }
            }
            try { _transport?.Dispose(); } catch { /* best-effort */ }
@@ -4,6 +4,7 @@ using System.Threading;
 using AutopilotMonitor.Agent.V2.Core.Logging;
 using AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Office;
 using AutopilotMonitor.DecisionCore.Engine;
+using Microsoft.Win32;

 namespace AutopilotMonitor.Agent.V2.Core.Orchestration
 {
@@ -49,9 +50,13 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
        private readonly OfficeInstallDetector _detector;
        private readonly OfficeProcessWatcher _processWatcher;
        private readonly AgentLogger _logger;
+        // Guards the fields below, nothing else. Never held across a call into a watcher or the
+        // detector: their callbacks come back into this host and take it.
        private readonly object _lock = new object();

        private readonly OfficeInstallStateData? _resumeState;
+        private readonly RegistryHive _registryHive;
+        private readonly string _registrySubKey;
        private RegistryChangeWatcher? _registryWatcher;
        private OfficeBinaryWatcher? _binaryWatcher;
        private bool _pathObserved;       // InstallationPath known → stop poking the DO collector
@@ -74,16 +79,42 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
            int settleSeconds,
            OfficeInstallStatePersistence? statePersistence = null,
            OfficeInstallStateData? resumeState = null)
+            : this(sessionId, tenantId, ingress, clock, logger, settleSeconds, statePersistence, resumeState,
+                  RegistryHive.LocalMachine, ClickToRunSubKey, snapshotProvider: null)
+        {
+        }
+
+        /// <summary>
+        /// Test seam: points the registry watcher at a key a test may write to and feeds the
+        /// detector synthetic snapshots. Production uses the constructor above.
+        /// </summary>
+        internal OfficeInstallDetectorHost(
+            string sessionId,
+            string tenantId,
+            ISignalIngressSink ingress,
+            IClock clock,
+            AgentLogger logger,
+            int settleSeconds,
+            OfficeInstallStatePersistence? statePersistence,
+            OfficeInstallStateData? resumeState,
+            RegistryHive registryHive,
+            string registrySubKey,
+            Func<OfficeC2RSnapshot>? snapshotProvider)
        {
            if (ingress == null) throw new ArgumentNullException(nameof(ingress));
            if (clock == null) throw new ArgumentNullException(nameof(clock));
            _logger = logger ?? throw new ArgumentNullException(nameof(logger));
            _resumeState = resumeState;
+            _registryHive = registryHive;
+            _registrySubKey = registrySubKey ?? throw new ArgumentNullException(nameof(registrySubKey));

            var post = new InformationalEventPost(ingress, clock);
            _detector = new OfficeInstallDetector(sessionId, tenantId, post, logger, clock,
                onInstallationPathObserved: OnInstallationPathObserved,
-                statePersistence: statePersistence);
+                statePersistence: statePersistence)
+            {
+                SnapshotProvider = snapshotProvider,
+            };
            _processWatcher = new OfficeProcessWatcher(logger, settleSeconds);
            _processWatcher.Started += OnWorkerStarted;
        }
@@ -108,12 +139,10 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
            // Arm the registry watcher up front (not at worker-start) so the early Scenario\INSTALL key
            // is caught before the (late) worker process. The watcher's bootstrap fallback handles the
            // case where the ClickToRun key does not exist yet on a clean first install.
-            lock (_lock)
-            {
-                _registryWatcher = new RegistryChangeWatcher(ClickToRunSubKey, _logger);
-                _registryWatcher.Changed += OnRegistryChanged;
-                _registryWatcher.Start();
-            }
+            var registryWatcher = new RegistryChangeWatcher(_registryHive, _registrySubKey, _logger);
+            registryWatcher.Changed += OnRegistryChanged;
+            lock (_lock) { _registryWatcher = registryWatcher; }
+            registryWatcher.Start();
            _processWatcher.Start();

            // Resume a persisted *Active* lifecycle (enrollments span reboots) AFTER the watchers are
@@ -134,7 +163,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
            // re-poking it on every registry value churn is pure log noise (field session 7da7dead).
            bool raise;
            lock (_lock) { raise = !_pathObserved && !_lifecycleEnded; }
-            if (raise)
+            // A callback can still be running after Dispose returned — Dispose never waits for one.
+            if (raise && Volatile.Read(ref _disposed) == 0)
            {
                try { OfficeExpected?.Invoke(this, EventArgs.Empty); }
                catch (Exception ex) { _logger.Warning($"[OfficeInstallDetectorHost] OfficeExpected handler threw: {ex.Message}"); }
@@ -147,15 +177,21 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration

        private void OnInstallationPathObserved(string? installationPath)
        {
+            OfficeBinaryWatcher watcher;
            lock (_lock)
            {
                _pathObserved = true; // stop raising OfficeExpected (lifecycle has started)
                if (_lifecycleEnded || _binaryWatcher != null || string.IsNullOrEmpty(installationPath)) return;
+                if (Volatile.Read(ref _disposed) == 1) return;

-                _binaryWatcher = new OfficeBinaryWatcher(installationPath!, OfficeInstallDetector.CoreBinaries, _logger);
-                _binaryWatcher.BinaryAppeared += OnBinaryAppeared;
-                _binaryWatcher.Start();
+                watcher = new OfficeBinaryWatcher(installationPath!, OfficeInstallDetector.CoreBinaries, _logger);
+                watcher.BinaryAppeared += OnBinaryAppeared;
+                _binaryWatcher = watcher;
            }
+
+            // Start can raise BinaryAppeared right away (Office already on disk), and that handler
+            // ends in DisposeWatchers.
+            watcher.Start();
        }

        private void OnBinaryAppeared(object? sender, EventArgs e)
@@ -191,20 +227,25 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration

        private void DisposeWatchers()
        {
+            RegistryChangeWatcher? registryWatcher;
+            OfficeBinaryWatcher? binaryWatcher;
            lock (_lock)
            {
-                if (_registryWatcher != null)
-                {
-                    try { _registryWatcher.Changed -= OnRegistryChanged; } catch { }
-                    try { _registryWatcher.Dispose(); } catch { }
-                    _registryWatcher = null;
-                }
-                if (_binaryWatcher != null)
-                {
-                    try { _binaryWatcher.BinaryAppeared -= OnBinaryAppeared; } catch { }
-                    try { _binaryWatcher.Dispose(); } catch { }
-                    _binaryWatcher = null;
-                }
+                registryWatcher = _registryWatcher;
+                _registryWatcher = null;
+                binaryWatcher = _binaryWatcher;
+                _binaryWatcher = null;
+            }
+
+            if (registryWatcher != null)
+            {
+                try { registryWatcher.Changed -= OnRegistryChanged; } catch { }
+                try { registryWatcher.Dispose(); } catch { }
+            }
+            if (binaryWatcher != null)
+            {
+                try { binaryWatcher.BinaryAppeared -= OnBinaryAppeared; } catch { }
+                try { binaryWatcher.Dispose(); } catch { }
            }
        }
    }
@@ -0,0 +1,137 @@
+#nullable enable
+using System;
+using System.Collections.Generic;
+using System.Threading;
+using AutopilotMonitor.Agent.V2.Core.Logging;
+using AutopilotMonitor.Agent.V2.Core.Monitoring.Interop;
+using AutopilotMonitor.Agent.V2.Core.Monitoring.Runtime;
+using AutopilotMonitor.Agent.V2.Core.Transport;
+using AutopilotMonitor.DecisionCore.Engine;
+using AutopilotMonitor.Shared;
+using AutopilotMonitor.Shared.Models;
+using Microsoft.Win32;
+
+namespace AutopilotMonitor.Agent.V2.Core.Orchestration
+{
+    /// <summary>
+    /// Tells <see cref="ProxyObserver"/> the moment proxy settings change, so the log has the exact
+    /// time. A watcher that fails costs only that time: the observer compares again on every failed
+    /// upload.
+    /// </summary>
+    internal sealed class ProxySettingsHost : ICollectorHost
+    {
+        private const string Source = "ProxySettingsHost";
+        private const int DebounceMs = 1000;
+
+        // The whole subtree: "Connections" does not exist yet in an account nothing has written to.
+        // HKCU of a SYSTEM process is HKU\S-1-5-18.
+        private const string AccountSettingsKey = @"Software\Microsoft\Windows\CurrentVersion\Internet Settings";
+        // Holds WinHttpSettings, which netsh winhttp writes.
+        private const string MachineConnectionsKey = @"SOFTWARE\Microsoft\Windows\CurrentVersion\Internet Settings\Connections";
+
+        private const RegistryNativeMethods.RegChangeNotifyFilter Filter =
+            RegistryNativeMethods.RegChangeNotifyFilter.Name |
+            RegistryNativeMethods.RegChangeNotifyFilter.LastSet;
+
+        private readonly ProxyObserver _observer;
+        private readonly InformationalEventPost _post;
+        private readonly AgentLogger _logger;
+        private readonly List<RegistryWatcher> _watchers = new List<RegistryWatcher>();
+        private readonly Timer _debounce;
+        private int _started;
+        private int _stopped;
+
+        public string Name => "ProxySettingsWatcher";
+
+        public ProxySettingsHost(
+            ProxyObserver observer,
+            ISignalIngressSink ingress,
+            IClock clock,
+            AgentLogger logger)
+        {
+            if (ingress == null) throw new ArgumentNullException(nameof(ingress));
+            if (clock == null) throw new ArgumentNullException(nameof(clock));
+            _observer = observer ?? throw new ArgumentNullException(nameof(observer));
+            _logger = logger ?? throw new ArgumentNullException(nameof(logger));
+            _post = new InformationalEventPost(ingress, clock);
+            _debounce = new Timer(_ => OnDebounceElapsed(), null, Timeout.Infinite, Timeout.Infinite);
+
+            AddWatcher(RegistryHive.CurrentUser, AccountSettingsKey, watchSubtree: true, "account settings");
+            AddWatcher(RegistryHive.LocalMachine, MachineConnectionsKey, watchSubtree: false, "WinHTTP settings");
+        }
+
+        private void AddWatcher(RegistryHive hive, string subKey, bool watchSubtree, string label)
+        {
+            var watcher = new RegistryWatcher(hive, subKey, watchSubtree, RegistryView.Registry64, Filter);
+            watcher.Changed += (_, _) => _debounce.Change(DebounceMs, Timeout.Infinite);
+            watcher.Error += (_, ex) => _logger.Warning($"ProxySettingsHost: {label} watcher error - {ex.GetType().Name}: {ex.Message}");
+            _watchers.Add(watcher);
+        }
+
+        public void Start()
+        {
+            if (Interlocked.Exchange(ref _started, 1) == 1) return;
+
+            _observer.SettingsChanged += OnSettingsChanged;
+            foreach (var watcher in _watchers)
+            {
+                try { watcher.Start(); }
+                catch (Exception ex) { _logger.Warning($"ProxySettingsHost: a watcher failed to start: {ex.Message}"); }
+            }
+
+            // Whatever moved between the baseline and the start of the watchers.
+            OnDebounceElapsed();
+        }
+
+        public void Stop()
+        {
+            if (Interlocked.Exchange(ref _stopped, 1) == 1) return;
+
+            DisposeWatchers();
+            _observer.SettingsChanged -= OnSettingsChanged;
+            if (Volatile.Read(ref _started) == 1) _observer.LogOpenFailures();
+        }
+
+        public void Dispose()
+        {
+            Stop();
+            _debounce.Dispose();
+        }
+
+        private void DisposeWatchers()
+        {
+            foreach (var watcher in _watchers)
+            {
+                try { watcher.Dispose(); }
+                catch (Exception ex) { _logger.Debug($"ProxySettingsHost: disposing a watcher threw: {ex.Message}"); }
+            }
+            _watchers.Clear();
+        }
+
+        private void OnDebounceElapsed()
+        {
+            _logger.Trace("ProxySettingsHost: checking the proxy settings.");
+            try { _observer.CheckForChange(); }
+            catch (Exception ex) { _logger.Warning($"ProxySettingsHost: checking the proxy settings failed: {ex.Message}"); }
+        }
+
+        /// <summary>
+        /// Waits in the spool if uploads are down, so the timeline explains the gap once they work
+        /// again. The portal shows the newest event of this type.
+        /// </summary>
+        private void OnSettingsChanged(ProxySettings settings, string what, string route)
+        {
+            var data = settings.ToEventData();
+            data["trigger"] = "changed";
+            data["change"] = what;
+            data["route"] = route;
+
+            _post.Emit(
+                eventType: Constants.EventTypes.ProxyConfiguration,
+                source: Source,
+                message: $"Proxy settings changed: {what}",
+                severity: EventSeverity.Warning,
+                typedPayload: data);
+        }
+    }
+}
@@ -1,10 +1,12 @@
 #nullable enable
 using System;
 using System.Collections.Generic;
+using System.Globalization;
 using System.Threading;
 using AutopilotMonitor.Agent.V2.Core.Logging;
 using AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals;
 using AutopilotMonitor.Agent.V2.Core.Monitoring.Runtime;
+using AutopilotMonitor.Agent.V2.Core.Persistence;
 using AutopilotMonitor.DecisionCore.Engine;
 using AutopilotMonitor.DecisionCore.Signals;
 using AutopilotMonitor.Shared;
@@ -21,11 +23,20 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
    /// It observes the central signal rail (<see cref="SignalIngress.SignalPosted"/>, the same
    /// hook <c>GatherRuleExecutorHost</c> uses for phase_change triggers):
    /// <list type="bullet">
-    ///   <item><b>Engage</b> when a signal reports the ESP phase as <c>AccountSetup</c>.</item>
+    ///   <item><b>Engage</b> when a signal reports the ESP phase as <c>AccountSetup</c> — unless the
+    ///     user-ESP page already closed in this enrollment (D-414). The page exit is latched in the
+    ///     <see cref="StartupEventGate"/>, because after an agent restart the AccountSetup phase
+    ///     reaches the rail again (IME logs it at the next sign-in, and the adapter's dedup lives
+    ///     per process).</item>
    ///   <item><b>Release</b> on <see cref="DecisionSignalKind.EspExiting"/> once the AccountSetup
    ///     registry shows progress (the real user-ESP page exit — see below), on
    ///     <see cref="Stop"/> (session teardown), or on the safety-cap timer (a backstop so a
    ///     device is never held awake for the agent's full max-lifetime).</item>
+    ///   <item><b>RealmJoin hand-over</b> (D-413): RealmJoin signals only exist when the tenant runs
+    ///     the RealmJoin Watcher. When RealmJoin was detected and is still Blank as the user-ESP
+    ///     page closes, the hold stays until RealmJoin leaves Blank (it keeps the device awake
+    ///     itself from there), bounded by <see cref="RealmJoinStartWaitMinutes"/>. RealmJoin
+    ///     leaving Blank ends any hold; once it has, the host does not engage in this process.</item>
    /// </list>
    /// The hold itself is owned by <see cref="KeepAwakeController"/>; the OS also auto-clears it
    /// on process exit / reboot, so it can never leak.
@@ -57,7 +68,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
    /// than host construction) means the ESP policy is already present in the registry. When the
    /// value is unavailable (ESP skipped, WDP v2 with no ESP, or unreadable) the cap falls back to
    /// <see cref="DefaultFallbackCapMinutes"/>. The resolved cap and its source are reported on the
-    /// <c>keep_awake_engaged</c> event for fleet-wide observability.
+    /// <c>keep_awake_engaged</c> event for fleet-wide observability. The RealmJoin wait replaces
+    /// this cap when the page closes: one timer, one bound per phase of the hold.
    /// </para>
    /// </summary>
    internal sealed class UserEspKeepAwakeHost : ICollectorHost
@@ -78,9 +90,20 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
        /// </summary>
        internal const int EspCapMarginMinutes = 30;

+        /// <summary>
+        /// How long the hold waits for RealmJoin to leave Blank after the user-ESP page closed
+        /// (D-413 has the measured start delays behind the value).
+        /// </summary>
+        internal const int RealmJoinStartWaitMinutes = 30;
+
+        /// <summary><see cref="StartupEventGate"/> latch: the user-ESP page closed in this enrollment (D-414).</summary>
+        internal const string UserEspPageClosedKey = "keep_awake.user_esp_page_closed";
+
        // Release reasons (carried on the keep_awake_released event payload). "account_setup_complete"
        // (release on the synthesized completion signal) was retired with q8n — see the class doc.
        internal const string ReasonUserEspExited = "user_esp_exited";
+        internal const string ReasonRealmJoinStarted = "realmjoin_started";
+        internal const string ReasonRealmJoinNotStarted = "realmjoin_not_started";
        internal const string ReasonHostStop = "host_stop";
        internal const string ReasonSafetyCap = "safety_cap";

@@ -92,13 +115,16 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
        private static readonly string AccountSetupPhaseName = EnrollmentPhase.AccountSetup.ToString();

        private readonly AgentLogger _logger;
+        private readonly IClock _clock;
        private readonly InformationalEventPost _post;
        private readonly KeepAwakeController _controller;
        private readonly SignalIngress? _observableIngress;
        private readonly int _fallbackCapMinutes;
        private readonly TimeSpan? _safetyCapOverride;
+        private readonly TimeSpan _realmJoinStartWait;
        private readonly Func<int?> _espTimeoutProvider;
        private readonly Func<bool> _accountSetupProgressProbe;
+        private readonly StartupEventGate? _startupGate;

        private enum HoldState { Idle, Engaging, Engaged, Released }

@@ -107,7 +133,16 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
        private Timer? _safetyCapTimer;
        private HoldState _state = HoldState.Idle;  // guarded by _gate
        private int _activeCapMinutes;              // guarded by _gate — for the cap-elapsed log line
+        private int _capGeneration;                 // guarded by _gate — a superseded timer callback is ignored
+        private bool _awaitingRealmJoin;            // guarded by _gate — page closed, RealmJoin still Blank
+        private DateTime _userEspExitedUtc;         // guarded by _gate — valid while _awaitingRealmJoin
        private int _disposed;
+        private int _pageClosedLatched;             // 0/1 — the latch write runs once per process
+
+        // RealmJoin observations of this process. Monotonic, written on the posting thread so the
+        // ThreadPool work that follows always sees them (0/1 for Volatile/Interlocked).
+        private int _realmJoinDetected;
+        private int _realmJoinStarted;

        public UserEspKeepAwakeHost(
            ISignalIngressSink ingress,
@@ -117,17 +152,20 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
            KeepAwakeController? controller = null,
            TimeSpan? safetyCapOverride = null,
            Func<int?>? espTimeoutProvider = null,
-            Func<bool>? accountSetupProgressProbe = null)
+            Func<bool>? accountSetupProgressProbe = null,
+            TimeSpan? realmJoinStartWaitOverride = null,
+            StartupEventGate? startupGate = null)
        {
            if (ingress == null) throw new ArgumentNullException(nameof(ingress));
-            if (clock == null) throw new ArgumentNullException(nameof(clock));
+            _clock = clock ?? throw new ArgumentNullException(nameof(clock));
            _logger = logger ?? throw new ArgumentNullException(nameof(logger));
            _post = new InformationalEventPost(ingress, clock, logger);
            _controller = controller ?? new KeepAwakeController(logger);
            _observableIngress = ingress as SignalIngress;
            _fallbackCapMinutes = fallbackCapMinutes > 0 ? fallbackCapMinutes : DefaultFallbackCapMinutes;
-            // safetyCapOverride is a test seam for a fixed (e.g. sub-second) cap.
+            // safetyCapOverride / realmJoinStartWaitOverride are test seams for fixed (e.g. sub-second) bounds.
            _safetyCapOverride = safetyCapOverride;
+            _realmJoinStartWait = realmJoinStartWaitOverride ?? TimeSpan.FromMinutes(RealmJoinStartWaitMinutes);
            // The ESP SyncFailureTimeout is read at engage time (the ESP policy is present by then).
            _espTimeoutProvider = espTimeoutProvider
                ?? (() => EspSkipConfigurationProbe.ReadFull(_logger).SyncFailureTimeoutMinutes);
@@ -135,6 +173,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
            // lasts until the safety cap (erring long, never early). Production always wires the
            // EspAndHelloHost probe (DefaultComponentFactory).
            _accountSetupProgressProbe = accountSetupProgressProbe ?? (() => false);
+            // Without a gate (tests) the page-closed latch is off and every agent run engages anew.
+            _startupGate = startupGate;
        }

        /// <summary>
@@ -180,21 +220,29 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
            // (which briefly waits on the keep-awake thread) is dispatched to the ThreadPool.
            try
            {
-                if (kind == DecisionSignalKind.EspExiting)
+                switch (kind)
                {
-                    // Only the user-ESP page exit releases: the Device→Account handoff 62407 arrives
-                    // before any AccountSetup subcategory has left notStarted, the real exit after.
-                    // Cheap to skip while idle; the probe is a locked dictionary scan.
-                    if (IsEngagedOrEngaging() && ProbeAccountSetupProgress())
-                        ThreadPool.QueueUserWorkItem(_ => SafeRelease(ReasonUserEspExited, EventSeverity.Info));
-                    return;
+                    case DecisionSignalKind.EspExiting:
+                        // Only the user-ESP page exit counts: the Device→Account handoff 62407 arrives
+                        // before any AccountSetup subcategory has left notStarted, the real exit after.
+                        // Checked in every hold state — the page-closed latch (D-414) must also be set
+                        // while idle, capped or waiting. The probe is a locked dictionary scan.
+                        if (ProbeAccountSetupProgress())
+                            ThreadPool.QueueUserWorkItem(_ => SafeRun(OnUserEspPageClosed, "user-ESP exit"));
+                        return;
+
+                    case DecisionSignalKind.RealmJoinDetected:
+                    case DecisionSignalKind.RealmJoinPhaseChanged:
+                    case DecisionSignalKind.RealmJoinResolved:
+                        ObserveRealmJoin(kind, payload);
+                        return;
                }

                if (payload != null
                    && payload.TryGetValue(SignalPayloadKeys.EspPhase, out var phaseName)
                    && string.Equals(phaseName, AccountSetupPhaseName, StringComparison.OrdinalIgnoreCase))
                {
-                    ThreadPool.QueueUserWorkItem(_ => SafeEngage());
+                    ThreadPool.QueueUserWorkItem(_ => SafeRun(Engage, "engage"));
                }
            }
            catch (Exception ex)
@@ -203,15 +251,30 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
            }
        }

-        private void SafeEngage()
+        /// <summary>
+        /// Records what the RealmJoin Watcher reported. The flags are set here, on the posting
+        /// thread, before any work is queued: the ThreadPool items run in no fixed order, and each
+        /// re-checks the hold state under <see cref="_gate"/>, so no hand-over is lost.
+        /// </summary>
+        private void ObserveRealmJoin(DecisionSignalKind kind, IReadOnlyDictionary<string, string>? payload)
        {
-            try { Engage(); }
-            catch (Exception ex) { _logger.Error("UserEspKeepAwakeHost: engage failed.", ex); }
+            Volatile.Write(ref _realmJoinDetected, 1);
+
+            // Resolved is phase 110 by definition; Detected and PhaseChanged carry the phase.
+            var leftBlank = kind == DecisionSignalKind.RealmJoinResolved
+                || (payload != null
+                    && payload.TryGetValue(DecisionEngine.RealmJoinPayloadKeys.DeploymentPhase, out var raw)
+                    && int.TryParse(raw, NumberStyles.Integer, CultureInfo.InvariantCulture, out var phase)
+                    && phase >= RealmJoinInfo.PhaseRunningThresholdMin);
+
+            if (leftBlank && Interlocked.Exchange(ref _realmJoinStarted, 1) == 0)
+                ThreadPool.QueueUserWorkItem(_ => SafeRun(OnRealmJoinStarted, "RealmJoin hand-over"));
        }

-        private bool IsEngagedOrEngaging()
+        private void SafeRun(Action work, string what)
        {
-            lock (_gate) { return _state == HoldState.Engaging || _state == HoldState.Engaged; }
+            try { work(); }
+            catch (Exception ex) { _logger.Error($"UserEspKeepAwakeHost: {what} failed.", ex); }
        }

        private bool ProbeAccountSetupProgress()
@@ -224,12 +287,6 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
            }
        }

-        private void SafeRelease(string reason, EventSeverity severity)
-        {
-            try { Release(reason, severity, emit: true); }
-            catch (Exception ex) { _logger.Error("UserEspKeepAwakeHost: release failed.", ex); }
-        }
-
        /// <summary>Engage the hold exactly once (Idle → Engaging → Engaged). No-op from any other state.</summary>
        private void Engage()
        {
@@ -239,6 +296,22 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
            lock (_gate)
            {
                if (_state != HoldState.Idle) return;
+                if (UserEspPageClosedEarlier())
+                {
+                    // Typically after an agent restart: the AccountSetup phase reached the rail
+                    // again, but the user-ESP page of this enrollment is already gone.
+                    _state = HoldState.Released;
+                    _logger.Info("UserEspKeepAwakeHost: the user-ESP page already closed in this enrollment — keep-awake not engaged.");
+                    return;
+                }
+                if (Volatile.Read(ref _realmJoinStarted) == 1)
+                {
+                    // Only after an agent restart: RealmJoin deploys (or is done) before the
+                    // AccountSetup phase is seen again — nothing left to hand over.
+                    _state = HoldState.Released;
+                    _logger.Info("UserEspKeepAwakeHost: RealmJoin has already started its deployment — keep-awake not engaged.");
+                    return;
+                }
                // L16 (delta review 2026-07-02): claim the transition, but run the controller's
                // Engage OUTSIDE the lock — it can block up to ~5 s on the keep-awake thread's
                // ready-wait, and holding _gate across that stalled a concurrent Stop→Release.
@@ -272,8 +345,9 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
                }

                _activeCapMinutes = capMinutes;
-                // One-shot backstop (NOT periodic): fire once after the cap, then release.
-                _safetyCapTimer = new Timer(OnSafetyCapElapsed, null, cap, Timeout.InfiniteTimeSpan);
+                // One-shot backstop (NOT periodic). The page may have closed while engaging — then
+                // the RealmJoin wait is the bound already.
+                ArmCapTimer(_awaitingRealmJoin ? _realmJoinStartWait : cap);
                _state = HoldState.Engaged;
            }

@@ -281,7 +355,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
            {
                ["osAccepted"] = osAccepted ? "true" : "false",
                ["scope"] = "system+display",
-                ["capMinutes"] = capMinutes.ToString(),
+                ["capMinutes"] = capMinutes.ToString(CultureInfo.InvariantCulture),
                ["capSource"] = capSource,
            });
        }
@@ -296,41 +370,151 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
            }
        }

+        /// <summary>
+        /// The user-ESP page closed. The fact is latched for later agent runs first. Without
+        /// RealmJoin, or with RealmJoin already past Blank, the hold ends here. With RealmJoin still
+        /// Blank it waits for the hand-over: the ESP-sized cap gives way to the RealmJoin wait.
+        /// </summary>
+        private void OnUserEspPageClosed()
+        {
+            LatchUserEspPageClosed();
+
+            lock (_gate)
+            {
+                if (_state != HoldState.Engaging && _state != HoldState.Engaged) return;
+                if (_awaitingRealmJoin) return; // a repeated exit signal
+
+                if (Volatile.Read(ref _realmJoinDetected) == 1 && Volatile.Read(ref _realmJoinStarted) == 0)
+                {
+                    _awaitingRealmJoin = true;
+                    _userEspExitedUtc = _clock.UtcNow;
+                    // While Engaging, Engage arms the wait when it completes.
+                    if (_state == HoldState.Engaged) ArmCapTimer(_realmJoinStartWait);
+                    _logger.Info($"UserEspKeepAwakeHost: user-ESP page closed before RealmJoin started its deployment — holding keep-awake until it starts (max {_realmJoinStartWait.TotalMinutes:0} min).");
+                    return;
+                }
+            }
+
+            Release(ReasonUserEspExited, EventSeverity.Info);
+        }
+
+        // MarkSucceeded persists at once (fail-soft): the page is gone for this enrollment.
+        private void LatchUserEspPageClosed()
+        {
+            if (_startupGate == null || Interlocked.Exchange(ref _pageClosedLatched, 1) == 1) return;
+            try { _startupGate.MarkSucceeded(UserEspPageClosedKey); }
+            catch (Exception ex) { _logger.Debug($"UserEspKeepAwakeHost: page-closed latch write threw: {ex.Message}"); }
+        }
+
+        // In-memory lookup (no I/O) — safe under _gate.
+        private bool UserEspPageClosedEarlier()
+        {
+            if (_startupGate == null) return false;
+            try { return _startupGate.AlreadySucceeded(UserEspPageClosedKey); }
+            catch (Exception ex)
+            {
+                _logger.Debug($"UserEspKeepAwakeHost: page-closed latch read threw: {ex.Message}");
+                return false;
+            }
+        }
+
+        /// <summary>RealmJoin left Blank — it keeps the device awake from here.</summary>
+        private void OnRealmJoinStarted()
+        {
+            Dictionary<string, string>? extra = null;
+            lock (_gate)
+            {
+                if (_state == HoldState.Released) return;
+                if (_state == HoldState.Idle)
+                {
+                    // Only after an agent restart (RealmJoin starts after the user-ESP page closed):
+                    // no hold to hand over, and none to take up later in this process.
+                    _state = HoldState.Released;
+                    _logger.Info("UserEspKeepAwakeHost: RealmJoin has already started its deployment — keep-awake will not engage.");
+                    return;
+                }
+                if (_awaitingRealmJoin)
+                {
+                    var waited = Math.Max(0, (_clock.UtcNow - _userEspExitedUtc).TotalSeconds);
+                    extra = new Dictionary<string, string>(StringComparer.Ordinal)
+                    {
+                        ["waitedSeconds"] = ((long)waited).ToString(CultureInfo.InvariantCulture),
+                    };
+                }
+            }
+
+            Release(ReasonRealmJoinStarted, EventSeverity.Info, extra);
+        }
+
        /// <summary>
        /// Release the hold exactly once (Idle/Engaging/Engaged → Released). Idempotent — a second
        /// call (or a competing completion / cap / stop trigger) is a no-op. A release that lands
        /// while an Engage is mid-flight (Engaging) wins: the engage path detects the final state
        /// after its blocking controller call and rolls the OS hold back (L16).
        /// </summary>
-        private void Release(string reason, EventSeverity severity, bool emit)
+        private void Release(string reason, EventSeverity severity, IReadOnlyDictionary<string, string>? extra = null)
        {
            bool wasEngaged;
            lock (_gate)
            {
                if (_state == HoldState.Released) return;
-                DisarmSafetyCap();
+                DisarmCapTimer();
                wasEngaged = _controller.Release();
                _state = HoldState.Released;
            }

-            if (wasEngaged && emit)
+            if (!wasEngaged) return;
+
+            var data = new Dictionary<string, string>(StringComparer.Ordinal) { ["reason"] = reason };
+            if (extra != null)
            {
-                Emit(Constants.EventTypes.KeepAwakeReleased, severity, new Dictionary<string, string>(StringComparer.Ordinal)
-                {
-                    ["reason"] = reason,
-                });
+                foreach (var kv in extra) data[kv.Key] = kv.Value;
            }
+            Emit(Constants.EventTypes.KeepAwakeReleased, severity, data);
        }

-        private void OnSafetyCapElapsed(object? state)
+        private void OnCapTimerElapsed(object? timerState)
        {
-            _logger.Warning($"UserEspKeepAwakeHost: safety cap ({_activeCapMinutes} min) elapsed without User-ESP completion — releasing keep-awake.");
-            SafeRelease(ReasonSafetyCap, EventSeverity.Warning);
+            string reason;
+            EventSeverity severity;
+            Dictionary<string, string>? extra = null;
+            lock (_gate)
+            {
+                // A timer replaced at the page exit can still fire once — only the current one counts.
+                if (!(timerState is int generation) || generation != _capGeneration || _state == HoldState.Released) return;
+
+                if (_awaitingRealmJoin)
+                {
+                    reason = ReasonRealmJoinNotStarted;
+                    severity = EventSeverity.Info;
+                    extra = new Dictionary<string, string>(StringComparer.Ordinal)
+                    {
+                        ["waitMinutes"] = ((int)Math.Round(_realmJoinStartWait.TotalMinutes)).ToString(CultureInfo.InvariantCulture),
+                    };
+                    _logger.Info($"UserEspKeepAwakeHost: RealmJoin did not start within {_realmJoinStartWait.TotalMinutes:0} min after the user-ESP page closed — releasing keep-awake.");
+                }
+                else
+                {
+                    reason = ReasonSafetyCap;
+                    severity = EventSeverity.Warning;
+                    _logger.Warning($"UserEspKeepAwakeHost: safety cap ({_activeCapMinutes} min) elapsed without User-ESP completion — releasing keep-awake.");
+                }
+            }
+
+            SafeRun(() => Release(reason, severity, extra), "release");
        }

        // Must be called under _gate.
-        private void DisarmSafetyCap()
+        private void ArmCapTimer(TimeSpan dueIn)
        {
+            DisarmCapTimer();
+            _safetyCapTimer = new Timer(OnCapTimerElapsed, _capGeneration, dueIn, Timeout.InfiniteTimeSpan);
+        }
+
+        // Must be called under _gate.
+        private void DisarmCapTimer()
+        {
+            _capGeneration++;
            var timer = _safetyCapTimer;
            _safetyCapTimer = null;
            try { timer?.Dispose(); } catch { }
@@ -369,7 +553,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration

            // Release synchronously on teardown. If a completion/cap release already won, this is a
            // no-op (state already Released). Emit is best-effort — the ingress may already be down.
-            Release(ReasonHostStop, EventSeverity.Info, emit: true);
+            Release(ReasonHostStop, EventSeverity.Info);
        }

        public void Dispose()
@@ -378,5 +562,11 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
            Stop();
            try { _controller.Dispose(); } catch { }
        }
+
+        // Test seam — the page closed while RealmJoin was still Blank and the hold now waits for it.
+        internal bool AwaitingRealmJoinForTest
+        {
+            get { lock (_gate) { return _awaitingRealmJoin; } }
+        }
    }
 }
@@ -46,6 +46,12 @@ namespace AutopilotMonitor.Agent.V2.Core.Security
    ///     authorized agent.</item>
    ///   <item>Any other coded 409 (<see cref="BackendRefusalException"/>) → <see cref="SessionRegistrationOutcome.Failed"/>
    ///     without retrying — a refusal with a code does not clear by waiting.</item>
+    ///   <item>410 from the backend (<see cref="BackendSessionGoneException"/>): the persisted
+    ///     session was deleted. With <c>rotateOnSessionGone</c> (a WhiteGlove Part 2 start, whose
+    ///     enrollment is only now continuing) the session is rotated like above and registered
+    ///     once more. Every other start returns <see cref="SessionRegistrationOutcome.SessionGone"/>
+    ///     without retrying — the caller ends monitoring. So does a second 410 or a failed rotation:
+    ///     the 48-hour break skips a WhiteGlove resume, so no path here may leave it retrying.</item>
    ///   <item>Any other exception on the last attempt → <see cref="EmergencyReporter.TrySendAsync"/>
    ///     with <c>AgentErrorType.RegisterSessionFailed</c> so operators see the final cause.</item>
    /// </list>
@@ -75,6 +81,10 @@ namespace AutopilotMonitor.Agent.V2.Core.Security
        /// Optional pre-registration link wait used by tests. Production callers pass
        /// <c>null</c> → <see cref="WaitForNetworkLinkAsync"/> (bounded by <see cref="NetworkLinkWaitMax"/>).
        /// </param>
+        /// <param name="rotateOnSessionGone">
+        /// True at a WhiteGlove Part 2 start: a 410 for the persisted session then becomes a new
+        /// session through <paramref name="rotateSession"/> instead of ending monitoring.
+        /// </param>
        public static async Task<SessionRegistrationResult> RegisterWithRetryAsync(
            BackendApiClient apiClient,
            AgentConfiguration agentConfig,
@@ -86,7 +96,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Security
            Func<Exception, Task> onTerminalTransportFailure = null,
            (string Manufacturer, string Model, string SerialNumber)? deviceHardware = null,
            Func<AgentLogger, Task> networkLinkWait = null,
-            Func<string> rotateSession = null)
+            Func<string> rotateSession = null,
+            bool rotateOnSessionGone = false)
        {
            if (apiClient == null) throw new ArgumentNullException(nameof(apiClient));
            if (agentConfig == null) throw new ArgumentNullException(nameof(agentConfig));
@@ -101,6 +112,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Security
            string lastError = null;
            Exception lastException = null;
            string rotatedFromSessionId = null;
+            string rotationReason = null;

            for (int attempt = 1; attempt <= MaxAttempts; attempt++)
            {
@@ -112,7 +124,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Security
                    if (response != null && response.Success)
                    {
                        logger.Info($"Session registered successfully: {response.SessionId} (validatedBy={response.ValidatedBy}, adminAction={response.AdminAction ?? "(none)"})");
-                        return SessionRegistrationResult.Succeeded(response, rotatedFromSessionId);
+                        return SessionRegistrationResult.Succeeded(response, rotatedFromSessionId, rotationReason);
                    }

                    lastError = response?.Message ?? "(null response)";
@@ -149,9 +161,40 @@ namespace AutopilotMonitor.Agent.V2.Core.Security
                        $"Backend refused registration with {Constants.AgentErrorCodes.SessionOwnerMismatch}: session {rotatedFromSessionId} " +
                        $"is not this device's (bound to another device identity after a re-enrollment without wipe, or claimed by another tenant). " +
                        $"Rotated to {newSessionId}; re-registering.");
+                    rotationReason = SessionRotationReasons.OwnerMismatch;
                    registration = BuildRegistration(agentConfig, agentVersion, deviceHardware);
                    continue;
                }
+                catch (BackendSessionGoneException ex)
+                {
+                    if (rotateOnSessionGone && rotateSession != null && rotatedFromSessionId == null)
+                    {
+                        var goneSessionId = registration.SessionId;
+                        string newSessionId = null;
+                        try
+                        {
+                            newSessionId = rotateSession();
+                        }
+                        catch (Exception rotateEx)
+                        {
+                            logger.Error($"Backend answered 410 for session {goneSessionId} but session rotation failed: {rotateEx.Message}", rotateEx);
+                        }
+
+                        if (newSessionId != null)
+                        {
+                            rotatedFromSessionId = goneSessionId;
+                            rotationReason = SessionRotationReasons.SessionGone;
+                            logger.Warning(
+                                $"Backend answered 410 for session {goneSessionId} at the start of a WhiteGlove Part 2: " +
+                                $"the session was deleted. Rotated to {newSessionId}; re-registering.");
+                            registration = BuildRegistration(agentConfig, agentVersion, deviceHardware);
+                            continue;
+                        }
+                    }
+
+                    logger.Error($"Session registration refused with 410 Gone — the backend deleted session {registration.SessionId}.");
+                    return SessionRegistrationResult.SessionGone(ex.StatusCode, ex.Message);
+                }
                catch (BackendRefusalException ex)
                {
                    logger.Error($"Session registration refused ({ex.StatusCode}, {ex.ErrorCode}): {ex.Message}");
@@ -294,6 +337,22 @@ namespace AutopilotMonitor.Agent.V2.Core.Security

        /// <summary>All attempts failed with non-auth errors (network, 5xx, malformed response).</summary>
        Failed = 2,
+
+        /// <summary>
+        /// 410 from the backend: the persisted session was deleted. No retry was attempted; the
+        /// caller ends monitoring and cleans up.
+        /// </summary>
+        SessionGone = 3,
+    }
+
+    /// <summary>Why a run registered under a new SessionId (<see cref="SessionRegistrationResult.RotationReason"/>).</summary>
+    public static class SessionRotationReasons
+    {
+        /// <summary>The backend refused the persisted id with <c>session_owner_mismatch</c>.</summary>
+        public const string OwnerMismatch = "owner_mismatch";
+
+        /// <summary>The backend answered 410 for the persisted id at a WhiteGlove Part 2 start.</summary>
+        public const string SessionGone = "session_gone";
    }

    /// <summary>Result of <see cref="SessionRegistrationHelper.RegisterWithRetryAsync"/>.</summary>
@@ -308,12 +367,15 @@ namespace AutopilotMonitor.Agent.V2.Core.Security
        public ValidatorType ValidatedBy => Response?.ValidatedBy ?? ValidatorType.Unknown;

        /// <summary>
-        /// SESSION-OWNER-BINDING: the SessionId this run started with when the backend refused it
-        /// with <c>session_owner_mismatch</c> and the session was rotated before the successful
+        /// The SessionId this run started with when the backend refused it (<c>session_owner_mismatch</c>,
+        /// or 410 at a WhiteGlove Part 2 start) and the session was rotated before the successful
        /// registration. Null on the normal path.
        /// </summary>
        public string RotatedFromSessionId { get; }

+        /// <summary>One of <see cref="SessionRotationReasons"/> when <see cref="RotatedFromSessionId"/> is set, else null.</summary>
+        public string RotationReason { get; }
+
        /// <summary>
        /// True when the run ended on a 401/403 that something on the network path answered (TLS
        /// inspection, a proxy page — <see cref="BackendAuthException.IsForeignResponse"/>), not
@@ -327,7 +389,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Security
            int httpStatusCode,
            string errorMessage,
            string rotatedFromSessionId = null,
-            bool isIntercepted = false)
+            bool isIntercepted = false,
+            string rotationReason = null)
        {
            Outcome = outcome;
            Response = response;
@@ -335,10 +398,16 @@ namespace AutopilotMonitor.Agent.V2.Core.Security
            ErrorMessage = errorMessage;
            RotatedFromSessionId = rotatedFromSessionId;
            IsIntercepted = isIntercepted;
+            RotationReason = rotatedFromSessionId != null ? rotationReason : null;
        }

-        public static SessionRegistrationResult Succeeded(RegisterSessionResponse response, string rotatedFromSessionId = null)
-            => new SessionRegistrationResult(SessionRegistrationOutcome.Succeeded, response, 200, null, rotatedFromSessionId);
+        public static SessionRegistrationResult Succeeded(
+            RegisterSessionResponse response, string rotatedFromSessionId = null, string rotationReason = null)
+            => new SessionRegistrationResult(
+                SessionRegistrationOutcome.Succeeded, response, 200, null, rotatedFromSessionId, rotationReason: rotationReason);
+
+        public static SessionRegistrationResult SessionGone(int statusCode, string message)
+            => new SessionRegistrationResult(SessionRegistrationOutcome.SessionGone, null, statusCode, message);

        public static SessionRegistrationResult AuthFailed(int statusCode, string message, bool intercepted = false)
            => new SessionRegistrationResult(SessionRegistrationOutcome.AuthFailed, null, statusCode, message, isIntercepted: intercepted);
@@ -324,7 +324,9 @@ namespace AutopilotMonitor.Agent.V2.Core.Termination
                // DeliveryOptimizationCollector, …) before the diagnostics ZIP is built so
                // late `performance_snapshot` / `agent_metrics_snapshot` events don't slip in
                // after `diagnostics_collecting` and the snapshot captured in the package
-                // matches the timeline. Best-effort — never blocks termination.
+                // matches the timeline. Best-effort, and bounded per host by the orchestrator:
+                // a collector that hangs is left behind, so the upload and the cleanup below
+                // still run.
                StopPeripheralCollectorsBestEffort();

                RunUploadDiagnosticsWithEvents(args);
@@ -0,0 +1,287 @@
+#nullable enable
+using System;
+using System.Globalization;
+using System.Threading.Tasks;
+using AutopilotMonitor.Agent.V2.Core.Logging;
+using AutopilotMonitor.DecisionCore.Engine;
+
+namespace AutopilotMonitor.Agent.V2.Core.Transport
+{
+    /// <summary>
+    /// Makes the agent log say which way uploads go and what happened to it. Something on the device
+    /// can change the proxy settings of the agent's account; .NET follows at once, and from then on
+    /// no channel may reach the backend, so the log on the device is the only witness.
+    /// <para>
+    /// Compares with what held at the start instead of judging a value: "no proxy" is the right
+    /// state on one network and the broken one on the next. Reads on failures and on registry
+    /// changes, never by polling. Nothing here throws into the upload path.
+    /// </para>
+    /// </summary>
+    public sealed class ProxyObserver
+    {
+        internal const string RouteUnknown = "unknown";
+
+        private static readonly TimeSpan DefaultRouteBound = TimeSpan.FromSeconds(3);
+
+        private readonly Func<ProxySettings> _readSettings;
+        private readonly Func<string> _readRoute;
+        private readonly IClock _clock;
+        private readonly AgentLogger _logger;
+        private readonly TimeSpan _routeBound;
+        private readonly object _sync = new object();
+
+        private ProxySettings? _current;
+        private string _lastRoute = RouteUnknown;
+        private Task<string>? _routeRead;
+        private DateTime? _uploadChangeAtUtc;
+        private string? _uploadChange;
+        private DateTime? _failingSinceUtc;
+        private int _failedAttempts;
+        private DateTime? _lastSuccessUtc;
+
+        /// <summary>Settings now, what changed, route now. Raised outside the lock, on the caller's thread.</summary>
+        internal event Action<ProxySettings, string, string>? SettingsChanged;
+
+        public ProxyObserver(string baseUrl, AgentLogger logger, IClock clock)
+            : this(
+                ProxySettingsReader.Read,
+                RouteReaderFor(baseUrl),
+                logger,
+                clock,
+                DefaultRouteBound)
+        {
+        }
+
+        internal ProxyObserver(
+            Func<ProxySettings> readSettings,
+            Func<string> readRoute,
+            AgentLogger logger,
+            IClock clock,
+            TimeSpan routeBound)
+        {
+            _readSettings = readSettings ?? throw new ArgumentNullException(nameof(readSettings));
+            _readRoute = readRoute ?? throw new ArgumentNullException(nameof(readRoute));
+            _logger = logger ?? throw new ArgumentNullException(nameof(logger));
+            _clock = clock ?? throw new ArgumentNullException(nameof(clock));
+            _routeBound = routeBound;
+        }
+
+        private static Func<string> RouteReaderFor(string baseUrl)
+        {
+            if (!Uri.TryCreate(baseUrl, UriKind.Absolute, out var target)) return () => RouteUnknown;
+            return () => ProxySettingsReader.ReadRoute(target);
+        }
+
+        /// <summary>Logs the state to compare against. Runs before the first request of the agent.</summary>
+        public void CaptureBaseline()
+        {
+            var settings = ReadSettingsSafe();
+            var route = ReadRouteBounded();
+            lock (_sync)
+            {
+                if (_current == null && !settings.IsUnreadable) _current = settings;
+                _lastRoute = route;
+            }
+            // Same text on a rebuild of the clients after an endpoint migration: the repeat goes to Trace.
+            _logger.Info($"ProxyObserver: start - {settings.DescribeAll()}; route to backend: {route}", repeatKey: "ProxyObserver.baseline");
+        }
+
+        /// <summary>Re-reads the settings and reports a change of content once, whoever notices it first.</summary>
+        public void CheckForChange()
+        {
+            var settings = ReadSettingsSafe();
+            if (settings.IsUnreadable) return;
+
+            ProxySettings previous;
+            var affectsUploads = false;
+            lock (_sync)
+            {
+                if (_current == null)
+                {
+                    _current = settings;
+                    return;
+                }
+                if (_current.Equals(settings)) return;
+
+                previous = _current;
+                _current = settings;
+                if (settings.DiffersForUploadsFrom(previous))
+                {
+                    affectsUploads = true;
+                    _uploadChangeAtUtc = _clock.UtcNow;
+                    _uploadChange = settings.DescribeUploadChangeFrom(previous);
+                }
+            }
+
+            var route = ReadRouteBounded();
+            string routeBefore;
+            lock (_sync)
+            {
+                routeBefore = _lastRoute;
+                _lastRoute = route;
+            }
+
+            var what = settings.DescribeChangeFrom(previous);
+            _logger.Warning(affectsUploads
+                ? $"ProxyObserver: proxy settings changed - {what}; route to backend: {(routeBefore == route ? route : $"{routeBefore} -> {route}")}. " +
+                  "The agent's uploads follow these settings. Check with: bitsadmin /util /getieproxy localsystem"
+                : $"ProxyObserver: proxy settings changed - {what}. The agent's uploads do not use WinHTTP, services that rely on its default do.");
+
+            try
+            {
+                SettingsChanged?.Invoke(settings, what, route);
+            }
+            catch (Exception ex)
+            {
+                _logger.Debug($"ProxyObserver: change handler threw: {ex.Message}");
+            }
+        }
+
+        /// <summary>The next hop to the backend: <c>direct</c>, <c>host:port</c> or <c>unknown</c>.</summary>
+        public string RouteText() => ReadRouteBounded();
+
+        /// <summary>
+        /// An upload did not reach the backend. The first of a series says what the reader needs to
+        /// know: when it began and whether the proxy settings moved before that.
+        /// </summary>
+        public void OnSendFailed(TimeSpan attemptDuration)
+        {
+            // Also catches a change the registry watcher did not report.
+            CheckForChange();
+
+            DateTime since;
+            DateTime? lastSuccess;
+            DateTime? changedAt;
+            string? change;
+            string? current;
+            lock (_sync)
+            {
+                _failedAttempts++;
+                if (_failingSinceUtc != null) return;
+
+                since = _clock.UtcNow - attemptDuration;
+                _failingSinceUtc = since;
+                lastSuccess = _lastSuccessUtc;
+                changedAt = _uploadChangeAtUtc;
+                change = _uploadChange;
+                current = _current?.Describe();
+            }
+
+            var route = ReadRouteBounded();
+            var lastUpload = lastSuccess == null ? "No successful upload yet." : $"Last successful upload {Time(lastSuccess.Value)}.";
+
+            if (changedAt != null && (lastSuccess == null || changedAt > lastSuccess))
+            {
+                _logger.Warning(
+                    $"ProxyObserver: uploads are failing since {Time(since)}, {Span(since - changedAt.Value)} after the proxy settings changed at {Time(changedAt.Value)} ({change}). " +
+                    $"Route to backend: {route}. {lastUpload}");
+            }
+            else
+            {
+                var unchangedSince = changedAt == null ? "start" : "the last successful upload";
+                _logger.Warning(
+                    $"ProxyObserver: uploads are failing since {Time(since)}. Proxy settings of this account unchanged since {unchangedSince}: {current ?? RouteUnknown}. " +
+                    $"Route to backend: {route}. {lastUpload}");
+            }
+        }
+
+        public void OnSendSucceeded()
+        {
+            DateTime since;
+            int attempts;
+            lock (_sync)
+            {
+                _lastSuccessUtc = _clock.UtcNow;
+                if (_failingSinceUtc == null) return;
+
+                since = _failingSinceUtc.Value;
+                attempts = _failedAttempts;
+                _failingSinceUtc = null;
+                _failedAttempts = 0;
+            }
+
+            CheckForChange();
+            _logger.Info($"ProxyObserver: uploads work again after {attempts} failed attempt(s) over {Span(_clock.UtcNow - since)}; route to backend: {ReadRouteBounded()}.");
+        }
+
+        /// <summary>The end of the log is read first, so a run that ends while failing says so there.</summary>
+        public void LogOpenFailures()
+        {
+            DateTime since;
+            int attempts;
+            DateTime? lastSuccess;
+            DateTime? changedAt;
+            string? change;
+            string? current;
+            lock (_sync)
+            {
+                if (_failingSinceUtc == null) return;
+
+                since = _failingSinceUtc.Value;
+                attempts = _failedAttempts;
+                lastSuccess = _lastSuccessUtc;
+                changedAt = _uploadChangeAtUtc;
+                change = _uploadChange;
+                current = _current?.Describe();
+            }
+
+            var lastUpload = lastSuccess == null ? "no successful upload" : $"last success {Time(lastSuccess.Value)}";
+            var settings = changedAt == null
+                ? $"Proxy settings of this account unchanged since start: {current ?? RouteUnknown}."
+                : $"Proxy settings changed at {Time(changedAt.Value)} ({change}).";
+            _logger.Warning(
+                $"ProxyObserver: stopping with uploads still failing: {attempts} failed attempt(s) since {Time(since)}, {lastUpload}, route to backend: {ReadRouteBounded()}. {settings}");
+        }
+
+        private ProxySettings ReadSettingsSafe()
+        {
+            try
+            {
+                var settings = _readSettings();
+                if (settings.IsUnreadable) _logger.Debug($"ProxyObserver: proxy settings {settings.Describe()}", repeatKey: "ProxyObserver.unreadable");
+                return settings;
+            }
+            catch (Exception ex)
+            {
+                _logger.Debug($"ProxyObserver: reading the proxy settings threw: {ex.Message}", repeatKey: "ProxyObserver.readThrew");
+                return ProxySettings.Unreadable(-1);
+            }
+        }
+
+        /// <summary>
+        /// Auto-detect can hang and must hold up neither the start nor an upload. A read still under
+        /// way is joined, so a hanging one does not pile up pool threads.
+        /// </summary>
+        private string ReadRouteBounded()
+        {
+            Task<string> read;
+            lock (_sync)
+            {
+                if (_routeRead == null || _routeRead.IsCompleted) _routeRead = Task.Run(ReadRouteSafe);
+                read = _routeRead;
+            }
+            return read.Wait(_routeBound) ? read.Result : RouteUnknown;
+        }
+
+        private string ReadRouteSafe()
+        {
+            try
+            {
+                return _readRoute();
+            }
+            catch (Exception ex)
+            {
+                _logger.Debug($"ProxyObserver: reading the route threw: {ex.Message}", repeatKey: "ProxyObserver.routeThrew");
+                return RouteUnknown;
+            }
+        }
+
+        private static string Time(DateTime utc) => utc.ToString("HH:mm:ss", CultureInfo.InvariantCulture);
+
+        private static string Span(TimeSpan span)
+        {
+            var seconds = Math.Max(0, (long)span.TotalSeconds);
+            return seconds < 120 ? $"{seconds} s" : $"{seconds / 60} min";
+        }
+    }
+}
@@ -0,0 +1,131 @@
+using System;
+using System.Collections.Generic;
+
+namespace AutopilotMonitor.Agent.V2.Core.Transport
+{
+    /// <summary>
+    /// The proxy settings Windows holds for the account this process runs as (what
+    /// <c>bitsadmin /util /getieproxy localsystem</c> shows for SYSTEM and what .NET uses), plus the
+    /// WinHTTP proxy (<c>netsh winhttp show proxy</c>). Compared by content, because WinINET rewrites
+    /// its settings blob without changing anything. The values end up in logs and events, so
+    /// credentials and PAC query strings are kept out on the way in.
+    /// </summary>
+    internal sealed class ProxySettings : IEquatable<ProxySettings>
+    {
+        internal const string CredentialsHidden = "(value with credentials, not shown)";
+
+        public bool AutoDetect { get; }
+        public string PacUrl { get; }
+        public string Proxy { get; }
+        public string Bypass { get; }
+        public string WinHttpProxy { get; }
+
+        /// <summary>Win32 error of a failed read; null when the settings were read.</summary>
+        public int? ReadError { get; }
+
+        public bool IsUnreadable => ReadError != null;
+
+        public ProxySettings(bool autoDetect, string pacUrl, string proxy, string bypass, string winHttpProxy)
+        {
+            AutoDetect = autoDetect;
+            PacUrl = SanitizeUrl(pacUrl);
+            Proxy = HideCredentials(proxy);
+            Bypass = EmptyToNull(bypass);
+            WinHttpProxy = HideCredentials(winHttpProxy);
+        }
+
+        private ProxySettings(int readError)
+        {
+            ReadError = readError;
+        }
+
+        public static ProxySettings Unreadable(int win32Error) => new ProxySettings(win32Error);
+
+        /// <summary>Kept in step with ANALYZE-CORR-003, which matches <c>Proxy|PAC</c>.</summary>
+        public string ProxyType =>
+            IsUnreadable ? "Unknown"
+            : Proxy != null ? "Proxy"
+            : PacUrl != null ? "PAC"
+            : AutoDetect ? "AutoDetect"
+            : "Direct";
+
+        public string Describe()
+        {
+            if (IsUnreadable) return $"unreadable (Win32 error {ReadError})";
+
+            var parts = new List<string>(3);
+            if (AutoDetect) parts.Add("auto-detect");
+            if (PacUrl != null) parts.Add($"PAC {PacUrl}");
+            if (Proxy != null) parts.Add($"proxy {Proxy}");
+            return parts.Count == 0 ? "no proxy" : string.Join(", ", parts);
+        }
+
+        public string DescribeWinHttp() => WinHttpProxy == null ? "direct" : $"proxy {WinHttpProxy}";
+
+        public string DescribeAll() => $"IE settings of this account: {Describe()}; WinHTTP: {DescribeWinHttp()}";
+
+        /// <summary>The account's own settings, which the agent's uploads follow; WinHTTP is apart.</summary>
+        public bool DiffersForUploadsFrom(ProxySettings other) =>
+            AutoDetect != other.AutoDetect
+            || PacUrl != other.PacUrl
+            || Proxy != other.Proxy
+            || Bypass != other.Bypass;
+
+        public string DescribeUploadChangeFrom(ProxySettings previous) =>
+            Describe() == previous.Describe()
+                ? "IE settings of this account: proxy bypass list changed"
+                : $"IE settings of this account: {previous.Describe()} -> {Describe()}";
+
+        public string DescribeChangeFrom(ProxySettings previous)
+        {
+            var parts = new List<string>(2);
+            if (DiffersForUploadsFrom(previous)) parts.Add(DescribeUploadChangeFrom(previous));
+            if (WinHttpProxy != previous.WinHttpProxy) parts.Add($"WinHTTP: {previous.DescribeWinHttp()} -> {DescribeWinHttp()}");
+            return string.Join("; ", parts);
+        }
+
+        /// <summary>Payload of the <c>proxy_configuration</c> event.</summary>
+        public Dictionary<string, object> ToEventData() => new Dictionary<string, object>
+        {
+            { "proxyType", ProxyType },
+            { "autoDetect", AutoDetect },
+            { "proxyEnabled", Proxy != null },
+            { "proxyServer", Proxy },
+            { "proxyOverride", Bypass },
+            { "autoConfigUrl", PacUrl },
+            { "winHttpProxyConfigured", WinHttpProxy != null },
+            { "winHttpProxy", WinHttpProxy },
+        };
+
+        public bool Equals(ProxySettings other) =>
+            other != null
+            && ReadError == other.ReadError
+            && !DiffersForUploadsFrom(other)
+            && WinHttpProxy == other.WinHttpProxy;
+
+        public override bool Equals(object obj) => Equals(obj as ProxySettings);
+
+        public override int GetHashCode() => (AutoDetect, PacUrl, Proxy, Bypass, WinHttpProxy, ReadError).GetHashCode();
+
+        private static string EmptyToNull(string value) => string.IsNullOrEmpty(value) ? null : value;
+
+        /// <summary>Scheme, host, port and path. A query string can carry a key; an unparsable URL is not repeated.</summary>
+        private static string SanitizeUrl(string url)
+        {
+            if (string.IsNullOrEmpty(url)) return null;
+            if (!Uri.TryCreate(url, UriKind.Absolute, out var uri) || string.IsNullOrEmpty(uri.Host)) return "(unparsable URL)";
+            var port = uri.IsDefaultPort ? string.Empty : $":{uri.Port}";
+            return $"{uri.Scheme}://{uri.Host}{port}{uri.AbsolutePath}";
+        }
+
+        /// <summary>
+        /// A proxy string has no defined form for credentials and a password can hold <c>=</c>,
+        /// <c>;</c> or <c>://</c>, so a value with an <c>@</c> is replaced as a whole, not taken apart.
+        /// </summary>
+        private static string HideCredentials(string proxy)
+        {
+            if (string.IsNullOrEmpty(proxy)) return null;
+            return proxy.IndexOf('@') < 0 ? proxy : CredentialsHidden;
+        }
+    }
+}
@@ -0,0 +1,67 @@
+using System;
+using System.Net;
+using System.Runtime.InteropServices;
+using AutopilotMonitor.Agent.V2.Core.Monitoring.Interop;
+
+namespace AutopilotMonitor.Agent.V2.Core.Transport
+{
+    internal static class ProxySettingsReader
+    {
+        public const string RouteDirect = "direct";
+
+        /// <summary>Reads the registry through WinHTTP, no network. Does not throw on a failed read.</summary>
+        public static ProxySettings Read()
+        {
+            var ie = new WinHttpNativeMethods.WINHTTP_CURRENT_USER_IE_PROXY_CONFIG();
+            var winHttp = new WinHttpNativeMethods.WINHTTP_PROXY_INFO();
+            try
+            {
+                if (!WinHttpNativeMethods.WinHttpGetIEProxyConfigForCurrentUser(ref ie))
+                {
+                    var error = Marshal.GetLastWin32Error();
+                    // The account has never had settings written, so nothing configures a proxy.
+                    if (error != WinHttpNativeMethods.ERROR_FILE_NOT_FOUND) return ProxySettings.Unreadable(error);
+                }
+
+                if (!WinHttpNativeMethods.WinHttpGetDefaultProxyConfiguration(ref winHttp))
+                {
+                    return ProxySettings.Unreadable(Marshal.GetLastWin32Error());
+                }
+
+                return new ProxySettings(
+                    autoDetect: ie.fAutoDetect,
+                    pacUrl: Marshal.PtrToStringUni(ie.lpszAutoConfigUrl),
+                    proxy: Marshal.PtrToStringUni(ie.lpszProxy),
+                    bypass: Marshal.PtrToStringUni(ie.lpszProxyBypass),
+                    winHttpProxy: winHttp.dwAccessType == WinHttpNativeMethods.WINHTTP_ACCESS_TYPE_NAMED_PROXY
+                        ? Marshal.PtrToStringUni(winHttp.lpszProxy)
+                        : null);
+            }
+            finally
+            {
+                Free(ie.lpszAutoConfigUrl);
+                Free(ie.lpszProxy);
+                Free(ie.lpszProxyBypass);
+                Free(winHttp.lpszProxy);
+                Free(winHttp.lpszProxyBypass);
+            }
+        }
+
+        /// <summary>
+        /// The next hop .NET chooses for <paramref name="target"/>: the same decision an
+        /// <c>HttpClientHandler</c> with default settings takes, PAC and auto-detect evaluated.
+        /// Auto-detect can take seconds on a network without WPAD.
+        /// </summary>
+        public static string ReadRoute(Uri target)
+        {
+            var hop = WebRequest.DefaultWebProxy?.GetProxy(target);
+            if (hop == null || string.Equals(hop.Host, target.Host, StringComparison.OrdinalIgnoreCase)) return RouteDirect;
+            return hop.IsDefaultPort ? hop.Host : $"{hop.Host}:{hop.Port}";
+        }
+
+        private static void Free(IntPtr memory)
+        {
+            if (memory != IntPtr.Zero) WinHttpNativeMethods.GlobalFree(memory);
+        }
+    }
+}
@@ -52,6 +52,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Transport.Telemetry
        private readonly Logging.AgentLogger? _logger;
        private readonly ServerCertificateObserver? _serverCertificates;
        private readonly NetworkMetrics? _networkMetrics;
+        private readonly ProxyObserver? _proxy;

        /// <param name="serverCertificates">
        /// Observer installed on the <paramref name="httpClient"/>'s handler; its issuer becomes
@@ -60,6 +61,9 @@ namespace AutopilotMonitor.Agent.V2.Core.Transport.Telemetry
        /// <param name="networkMetrics">
        /// Counts 2xx answers without the correlation echo (<c>agent_metrics_snapshot</c>). Null = not counted.
        /// </param>
+        /// <param name="proxy">
+        /// Names the route in the failure lines and hears how each upload ended. Null = neither.
+        /// </param>
        public BackendTelemetryUploader(
            HttpClient httpClient,
            string baseUrl,
@@ -72,7 +76,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Transport.Telemetry
            AuthFailureTracker? authFailureTracker = null,
            Logging.AgentLogger? logger = null,
            ServerCertificateObserver? serverCertificates = null,
-            NetworkMetrics? networkMetrics = null)
+            NetworkMetrics? networkMetrics = null,
+            ProxyObserver? proxy = null)
        {
            _httpClient = httpClient ?? throw new ArgumentNullException(nameof(httpClient));
            if (string.IsNullOrEmpty(baseUrl)) throw new ArgumentException("BaseUrl is mandatory.", nameof(baseUrl));
@@ -89,6 +94,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Transport.Telemetry
            _logger = logger;
            _serverCertificates = serverCertificates;
            _networkMetrics = networkMetrics;
+            _proxy = proxy;
        }

        public async Task<UploadResult> UploadBatchAsync(
@@ -153,7 +159,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Transport.Telemetry
                catch (TaskCanceledException ex)
                {
                    sw.Stop();
-                    _logger?.Warning($"BackendTelemetryUploader: ingest TIMEOUT after {sw.ElapsedMilliseconds}ms (corr={correlationId}, items={items.Count}): {ex.Message}");
+                    _logger?.Warning($"BackendTelemetryUploader: ingest TIMEOUT after {sw.ElapsedMilliseconds}ms (corr={correlationId}, items={items.Count}{RouteSuffix()}): {ex.Message}");
+                    _proxy?.OnSendFailed(sw.Elapsed);
                    // HttpClient timeout (not caller cancellation) surfaces as TaskCanceledException
                    // with cancellationToken.IsCancellationRequested == false.
                    return UploadResult.Transient($"timeout: {ex.Message}");
@@ -161,9 +168,11 @@ namespace AutopilotMonitor.Agent.V2.Core.Transport.Telemetry
                catch (HttpRequestException ex)
                {
                    sw.Stop();
-                    _logger?.Warning($"BackendTelemetryUploader: ingest NETWORK fail after {sw.ElapsedMilliseconds}ms (corr={correlationId}, items={items.Count}): {ex.Message}");
+                    var cause = TransportErrorCodes.DescribeSendFailure(ex);
+                    _logger?.Warning($"BackendTelemetryUploader: ingest NETWORK fail after {sw.ElapsedMilliseconds}ms (corr={correlationId}, items={items.Count}{RouteSuffix()}): {cause}");
+                    _proxy?.OnSendFailed(sw.Elapsed);
                    // DNS failure, socket error, etc. — network-layer is retryable.
-                    return UploadResult.Transient($"network: {ex.Message}");
+                    return UploadResult.Transient($"network: {cause}");
                }

                using (response)
@@ -174,6 +183,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Transport.Telemetry
                    if (result.Success)
                    {
                        _logger?.Verbose($"BackendTelemetryUploader: ingest OK (corr={correlationId}, items={items.Count}, firstId={items[0].TelemetryItemId}, lastId={items[items.Count - 1].TelemetryItemId}, bytes={compressedBody.Length}, durationMs={sw.ElapsedMilliseconds}, status={(int)response.StatusCode}).");
+                        _proxy?.OnSendSucceeded();
                    }
                    else if (result.IsTransient)
                    {
@@ -188,7 +198,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Transport.Telemetry
                            $"BackendTelemetryUploader: ingest INTERCEPTED — the answer did not come from the backend " +
                            $"(corr={correlationId}, items={items.Count}, durationMs={sw.ElapsedMilliseconds}, status={interception.StatusCode}, " +
                            $"reason={interception.ForeignReason}, pageTitle=\"{interception.PageTitle ?? "(none)"}\", " +
-                            $"serverCertIssuer=\"{interception.ServerCertIssuer ?? "(unknown)"}\").");
+                            $"serverCertIssuer=\"{interception.ServerCertIssuer ?? "(unknown)"}\"{RouteSuffix()}).");
+                        _proxy?.OnSendFailed(sw.Elapsed);
                    }
                    else if (result.IsSessionGone)
                    {
@@ -204,6 +215,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Transport.Telemetry
            }
        }

+        private string RouteSuffix() => _proxy == null ? string.Empty : $", route={_proxy.RouteText()}";
+
        private async Task<UploadResult> MapResponseAsync(HttpResponseMessage response, string correlationId)
        {
            var statusCode = (int)response.StatusCode;
@@ -78,7 +78,7 @@
  </ItemGroup>

  <ItemGroup>
-    <PackageReference Include="Newtonsoft.Json" Version="13.0.3" />
+    <PackageReference Include="Newtonsoft.Json" Version="13.0.4" />
  </ItemGroup>

  <!-- Plan §2.16 strict separation rule — build-time enforcement. -->
@@ -257,7 +257,7 @@ namespace AutopilotMonitor.Agent.V2
        /// <c>true</c> when the file-based <c>enrollment-complete.marker</c> signals that a
        /// previous session already completed enrollment — written by
        /// <see cref="EndMonitoringAtStart"/> (emergency break, intercepted-registration give-up,
-        /// config kill signal) right before it fires the cleanup retry, so that a next-boot observing the marker exits
+        /// session gone at registration, config kill signal) right before it fires the cleanup retry, so that a next-boot observing the marker exits
        /// cleanly even if the cleanup retry failed to remove the Scheduled Task. Triggers another
        /// self-destruct attempt when <paramref name="selfDestructOnComplete"/> is set.
        /// <para>
@@ -369,10 +369,11 @@ namespace AutopilotMonitor.Agent.V2
        /// next start exits cleanly even if the cleanup retry fails (Scheduled Task still alive,
        /// files locked, …), runs the cleanup retry when <paramref name="runSelfDestruct"/> is set
        /// (the emergency break and the give-up pass <c>SelfDestructOnComplete</c>, the kill signal
-        /// forces it), and deletes the persisted session files. Shared by the session-age emergency
-        /// break, the intercepted-registration give-up
-        /// (<c>BackendSessionRegistration.ConcludeFailedRun</c>) and the config-channel kill signal
-        /// so all three leave the device in the same state. Never throws.
+        /// and the session-gone end force it), and deletes the persisted session files. Shared by
+        /// the session-age emergency break, the intercepted-registration give-up
+        /// (<c>BackendSessionRegistration.ConcludeFailedRun</c>), the registration answered with 410
+        /// (<c>BackendSessionRegistration.ConcludeSessionGone</c>) and the config-channel kill signal
+        /// so all four leave the device in the same state. Never throws.
        /// </summary>
        internal static void EndMonitoringAtStart(
            string stateDirectory,
@@ -275,7 +275,9 @@ namespace AutopilotMonitor.Agent.V2
            // mapping + on-failure client disposal) is encapsulated in BackendSessionRegistration.
            // Exit codes: 6 = AuthFailed, 7 = anything else. A registration intercepted on more
            // starts than the buffer allows cleans up like the emergency break (state folder +
-            // cleanup factory) and still exits 6. See Runtime/BackendSessionRegistration.cs.
+            // cleanup factory) and still exits 6. A registration the backend answers with 410
+            // (session deleted) cleans up the same way and exits 0; a WhiteGlove Part 2 start
+            // registers a new session instead. See Runtime/BackendSessionRegistration.cs.
            var registration = Runtime.BackendSessionRegistration.Register(
                bootstrap.AgentConfig, auth, telemetry.MtlsHttpClient, GetAgentVersion(), consoleMode, logger,
                rotateSession: () => Runtime.BackendSessionRegistration.RotateSession(
@@ -283,7 +285,8 @@ namespace AutopilotMonitor.Agent.V2
                sessionPersistence: bootstrap.SessionPersistence,
                configFetchOutcome: runtimeConfig.RemoteConfigService.LastFetchOutcome.ToString(),
                stateDirectory: stateSubdir,
-                cleanupServiceFactory: bootstrap.CleanupServiceFactory);
+                cleanupServiceFactory: bootstrap.CleanupServiceFactory,
+                isWhiteGloveResume: bootstrap.IsWhiteGloveResume);
            if (registration.ShouldExit)
            {
                return registration.ExitCode;
@@ -99,7 +99,8 @@ namespace AutopilotMonitor.Agent.V2.Runtime
                // Measured, not guessed: the reducer snapshot is rewritten on every decision step,
                // so its mtime is the last moment the previous run is known to have been alive —
                // and unlike LastBootUtc it exists for every exit type, exception_crash included.
-                previousRunLastAliveUtc: DefaultComponentFactory.ReadPreviousRunLastAliveUtc(stateSubdir));
+                previousRunLastAliveUtc: DefaultComponentFactory.ReadPreviousRunLastAliveUtc(stateSubdir),
+                proxyObserver: auth.ProxyObserver);

            var whiteGloveSealingPatternIds = (System.Collections.Generic.IReadOnlyCollection<string>)remoteConfig.WhiteGloveSealingPatternIds
                ?? Array.Empty<string>();
@@ -346,7 +347,8 @@ namespace AutopilotMonitor.Agent.V2.Runtime
                            lifecyclePost = new InformationalEventPost(ingress, SystemClock.Instance, logger);
                            LifecycleEmitters.EmitAgentStarted(lifecyclePost, agentConfig, previousExit, agentVersion, remoteConfigService, logger,
                                rotatedFromSessionId: registrationResult?.RotatedFromSessionId,
-                                priorRegistrationFailures: registration.PriorFailures);
+                                priorRegistrationFailures: registration.PriorFailures,
+                                sessionRotationReason: registrationResult?.RotationReason);
                            // Wire-visible signal that the agent is running on defaults/cache
                            // rather than the live tenant config — closes the cold-start
                            // blind spot observed in session 8f2bef72 (2026-05-19).
@@ -52,6 +52,10 @@ namespace AutopilotMonitor.Agent.V2.Runtime
            // outbound call (legacy BackendApiClient calls + dominant /api/agent/telemetry POSTs).
            var networkMetrics = new NetworkMetrics();

+            // Before the first request, so a registration that fails has the route in the log too.
+            var proxyObserver = new ProxyObserver(agentConfig.ApiBaseUrl, logger, SystemClock.Instance);
+            proxyObserver.CaptureBaseline();
+
            var hardware = HardwareInfo.GetHardwareInfo(logger);

            // Resolve the MDM client cert when cert-mode is on. Cert-missing is non-fatal here:
@@ -150,6 +154,7 @@ namespace AutopilotMonitor.Agent.V2.Runtime
                emergencyReporter: emergencyReporter,
                authFailureTracker: authFailureTracker,
                serverCertificates: serverCertificates,
+                proxyObserver: proxyObserver,
                clientCertificateThumbprint: clientCertificate?.Thumbprint);
        }

@@ -201,7 +206,8 @@ namespace AutopilotMonitor.Agent.V2.Runtime
                    authFailureTracker: auth.AuthFailureTracker,
                    logger: logger,      // Plan §5 Fix 5 — upload-cadence logging
                    serverCertificates: auth.ServerCertificates,
-                    networkMetrics: auth.NetworkMetrics);
+                    networkMetrics: auth.NetworkMetrics,
+                    proxy: auth.ProxyObserver);
            }
            catch (Exception ex)
            {
@@ -291,6 +297,9 @@ namespace AutopilotMonitor.Agent.V2.Runtime
        /// </summary>
        public ServerCertificateObserver ServerCertificates { get; }

+        /// <summary>Shared by the telemetry uploader built in Phase 5 and the collector host.</summary>
+        public ProxyObserver ProxyObserver { get; }
+
        /// <summary>
        /// Thumbprint of the client certificate this run uses; null without one. Kept beside a
        /// failed run's record so the next successful start can tell whether the certificate changed.
@@ -308,6 +317,7 @@ namespace AutopilotMonitor.Agent.V2.Runtime
            EmergencyReporter emergencyReporter,
            AuthFailureTracker authFailureTracker,
            ServerCertificateObserver serverCertificates,
+            ProxyObserver proxyObserver,
            string clientCertificateThumbprint = null)
        {
            BackendApiClient = backendApiClient;
@@ -320,6 +330,7 @@ namespace AutopilotMonitor.Agent.V2.Runtime
            EmergencyReporter = emergencyReporter;
            AuthFailureTracker = authFailureTracker;
            ServerCertificates = serverCertificates;
+            ProxyObserver = proxyObserver;
            ClientCertificateThumbprint = clientCertificateThumbprint;
        }
    }
@@ -26,6 +26,9 @@ namespace AutopilotMonitor.Agent.V2.Runtime
    /// the next boot. The failed run is recorded for the emergency break report. A registration
    /// that something on the network path answered gets <c>InterceptedRegistrationRetryBoots</c>
    /// further boots, then the agent cleans up like the emergency break (<see cref="ConcludeFailedRun"/>).
+    /// A registration the backend answers with 410 — the session was deleted — ends monitoring at
+    /// once (<see cref="ConcludeSessionGone"/>); only a WhiteGlove Part 2 start registers a new
+    /// session instead, because its enrollment is only now continuing.
    /// A successful registration after failed starts reports them on <c>agent_started</c>
    /// (<see cref="ClearAfterSuccess"/>).
    /// </summary>
@@ -37,8 +40,9 @@ namespace AutopilotMonitor.Agent.V2.Runtime
        /// </summary>
        internal static readonly TimeSpan PendingDistressBound = TimeSpan.FromSeconds(5);

-        /// <param name="stateDirectory">State folder for <c>enrollment-complete.marker</c> on the intercepted-registration give-up.</param>
-        /// <param name="cleanupServiceFactory">Self-destruct for the give-up (run when <c>SelfDestructOnComplete</c>).</param>
+        /// <param name="stateDirectory">State folder for <c>enrollment-complete.marker</c> on the intercepted-registration give-up and the session-gone end.</param>
+        /// <param name="cleanupServiceFactory">Self-destruct for the give-up (run when <c>SelfDestructOnComplete</c>) and the session-gone end (always run).</param>
+        /// <param name="isWhiteGloveResume">This start is a WhiteGlove Part 2: a 410 for the persisted session becomes a new session.</param>
        public static SessionRegistrationOutcomeResult Register(
            AgentConfiguration agentConfig,
            BackendAuthBundle auth,
@@ -50,7 +54,8 @@ namespace AutopilotMonitor.Agent.V2.Runtime
            SessionIdPersistence sessionPersistence = null,
            string configFetchOutcome = null,
            string stateDirectory = null,
-            Func<CleanupService> cleanupServiceFactory = null)
+            Func<CleanupService> cleanupServiceFactory = null,
+            bool isWhiteGloveResume = false)
        {
            if (agentConfig == null) throw new ArgumentNullException(nameof(agentConfig));
            if (auth == null) throw new ArgumentNullException(nameof(auth));
@@ -86,7 +91,8 @@ namespace AutopilotMonitor.Agent.V2.Runtime
                // Reuse the single hardened hardware read from the auth bundle so the session row
                // matches the security headers the backend validated against (no second WMI query).
                deviceHardware: (auth.Manufacturer, auth.Model, auth.SerialNumber),
-                rotateSession: rotateSession)
+                rotateSession: rotateSession,
+                rotateOnSessionGone: isWhiteGloveResume)
                .GetAwaiter().GetResult();

            if (registrationResult.Outcome == SessionRegistrationOutcome.Succeeded)
@@ -97,6 +103,17 @@ namespace AutopilotMonitor.Agent.V2.Runtime
                        startContext.DeviceBootUtc, auth.ClientCertificateThumbprint));
            }

+            if (registrationResult.Outcome == SessionRegistrationOutcome.SessionGone)
+            {
+                // The report goes out through the auth bundle's client: dispose only afterwards.
+                var exitCode = ConcludeSessionGone(
+                    agentConfig, auth.EmergencyReporter, sessionPersistence, stateDirectory,
+                    cleanupServiceFactory, consoleMode, logger);
+                try { mtlsHttpClient?.Dispose(); } catch { }
+                try { auth.BackendApiClient?.Dispose(); } catch { }
+                return SessionRegistrationOutcomeResult.Exit(exitCode);
+            }
+
            var record = RecordFailedRun(
                sessionPersistence, registrationResult, startedUtc, DateTime.UtcNow,
                linkUpAtStart, TryIsNetworkLinkUp(), configFetchOutcome, NetworkFingerprint.TryCapture(), logger,
@@ -264,6 +281,41 @@ namespace AutopilotMonitor.Agent.V2.Runtime
            return registrationResult.Outcome == SessionRegistrationOutcome.AuthFailed ? 6 : 7;
        }

+        /// <summary>
+        /// The end of a start whose registration the backend answered with 410: the session was
+        /// deleted. One report over the emergency channel (a deleted session has no timeline to
+        /// carry an event), then monitoring ends like on the telemetry-channel 410 — marker first,
+        /// self-destruct regardless of <c>SelfDestructOnComplete</c>, session files deleted
+        /// (<see cref="Program.EndMonitoringAtStart"/>). Returns exit code 0: an intended end.
+        /// </summary>
+        internal static int ConcludeSessionGone(
+            AgentConfiguration agentConfig,
+            EmergencyReporter emergencyReporter,
+            SessionIdPersistence sessionPersistence,
+            string stateDirectory,
+            Func<CleanupService> cleanupServiceFactory,
+            bool consoleMode,
+            AgentLogger logger)
+        {
+            logger.Error(
+                $"=== SESSION GONE (HTTP 410): the backend deleted session {agentConfig.SessionId} — " +
+                "reporting once over the emergency channel, then cleaning up with self-destruct. ===");
+            if (consoleMode)
+                Console.Error.WriteLine("Session was deleted in the backend. Cleaning up and exiting.");
+
+            SessionGoneReport.SendBlocking(
+                emergencyReporter,
+                AgentErrorType.RegistrationRejectedSessionGone,
+                "Session registration rejected with HTTP 410 — the backend deleted this session. Agent cleaning up with self-destruct.",
+                logger);
+
+            Program.EndMonitoringAtStart(
+                stateDirectory, sessionPersistence, runSelfDestruct: true, cleanupServiceFactory, logger,
+                markerText: $"Session gone at {DateTime.UtcNow:O} (registration refused with HTTP 410)",
+                cleanupReason: "session_gone");
+            return 0;
+        }
+
        /// <summary>
        /// Boot times derived from the uptime counter jitter by milliseconds to seconds between two
        /// reads of the same boot (NTP corrections shift them further), so only a gap above this
@@ -47,7 +47,8 @@ namespace AutopilotMonitor.Agent.V2.Runtime
            RemoteConfigService remoteConfigService,
            AgentLogger logger,
            string rotatedFromSessionId = null,
-            PriorRegistrationFailures priorRegistrationFailures = null)
+            PriorRegistrationFailures priorRegistrationFailures = null,
+            string sessionRotationReason = null)
        {
            try
            {
@@ -72,9 +73,10 @@ namespace AutopilotMonitor.Agent.V2.Runtime
                    { "diagnosticsUploadMode", agentConfig.DiagnosticsUploadMode ?? "Off" },
                    { "previousExitType", previousExit?.ExitType ?? "unknown" },
                    { "unrestrictedMode", agentConfig.UnrestrictedMode },
-                    // SESSION-OWNER-BINDING: true when the backend refused the persisted session
-                    // id (session_owner_mismatch) and this run rotated to a new session before
-                    // registering — the re-enroll-without-wipe shape, made visible on the timeline.
+                    // True when the backend refused the persisted session id and this run rotated
+                    // to a new session before registering: session_owner_mismatch (re-enroll
+                    // without wipe) or 410 at a WhiteGlove Part 2 start (session deleted).
+                    // sessionRotationReason below names which.
                    { "sessionRotated", rotatedFromSessionId != null },
                    { "previousSessionId", rotatedFromSessionId ?? string.Empty },
                    // remoteConfigFetched answers "is the agent running on a live-fetched
@@ -96,6 +98,9 @@ namespace AutopilotMonitor.Agent.V2.Runtime
                if (recovered)
                    data["remoteConfigRecovered"] = true;

+                if (rotatedFromSessionId != null && !string.IsNullOrEmpty(sessionRotationReason))
+                    data["sessionRotationReason"] = sessionRotationReason;
+
                // Which bootstrap installed this agent (installer and loader versions, MSI or
                // Intune loader, OOBE go-script), read from the scripts' own logs: makes the
                // fleet's share of old or directly assigned installers countable.
@@ -1,6 +1,5 @@
 using System;
 using System.Collections.Generic;
-using System.Net;
 using System.Threading;
 using System.Threading.Tasks;
 using AutopilotMonitor.Agent.V2.Core.Configuration;
@@ -193,14 +192,6 @@ namespace AutopilotMonitor.Agent.V2.Runtime
            };
        }

-        // Bounded blocking send for the one session-gone report: the terminate that follows ends
-        // the process and the cleanup script deletes the agent, so a fire-and-forget send would
-        // be abandoned mid-flight. Retries stay inside one anti-flood reservation (ONE report).
-        private const int SessionGoneReportAttempts = 2;
-        private static readonly TimeSpan SessionGoneReportTimeout = TimeSpan.FromSeconds(15);
-        private static readonly TimeSpan SessionGoneReportRetryDelay = TimeSpan.FromSeconds(3);
-        private static readonly TimeSpan SessionGoneReportBudget = TimeSpan.FromSeconds(40);
-
        /// <summary>
        /// The backend answered HTTP 410 for the current session's telemetry: the session is over
        /// server-side. (a) Send ONE <see cref="AgentErrorType.TelemetryRejectedSessionUnknown"/>
@@ -227,25 +218,11 @@ namespace AutopilotMonitor.Agent.V2.Runtime

            logger.Error($"Backend no longer knows this session (HTTP 410: {reason}) — reporting once over the emergency channel, then terminating with self-destruct.");

-            if (emergencyReporter != null)
-            {
-                try
-                {
-                    emergencyReporter
-                        .TrySendAsync(
-                            AgentErrorType.TelemetryRejectedSessionUnknown,
-                            $"Telemetry upload rejected with HTTP 410 — backend no longer knows this session ({reason}). Agent terminating with self-destruct.",
-                            httpStatusCode: (int)HttpStatusCode.Gone,
-                            attempts: SessionGoneReportAttempts,
-                            perAttemptTimeout: SessionGoneReportTimeout,
-                            retryDelay: SessionGoneReportRetryDelay)
-                        .Wait(SessionGoneReportBudget);
-                }
-                catch (Exception ex)
-                {
-                    logger.Debug($"Session-gone report send failed (best-effort): {ex.Message}");
-                }
-            }
+            SessionGoneReport.SendBlocking(
+                emergencyReporter,
+                AgentErrorType.TelemetryRejectedSessionUnknown,
+                $"Telemetry upload rejected with HTTP 410 — backend no longer knows this session ({reason}). Agent terminating with self-destruct.",
+                logger);

            var terminateAction = new ServerAction
            {
@@ -0,0 +1,50 @@
+using System;
+using System.Net;
+using AutopilotMonitor.Agent.V2.Core.Logging;
+using AutopilotMonitor.Agent.V2.Core.Monitoring.Transport;
+using AutopilotMonitor.Shared.Models;
+
+namespace AutopilotMonitor.Agent.V2.Runtime
+{
+    /// <summary>
+    /// The one emergency report an agent sends when the backend answered HTTP 410 for its own
+    /// session — on a telemetry upload (<see cref="ServerControlPlane.HandleSessionGone"/>) or at
+    /// registration (<see cref="BackendSessionRegistration"/>). The send blocks within a bound:
+    /// the caller ends the process right after and the cleanup deletes the agent, so a
+    /// fire-and-forget send would be abandoned mid-flight. Retries stay inside one anti-flood
+    /// reservation (ONE report). Never throws.
+    /// </summary>
+    internal static class SessionGoneReport
+    {
+        private const int Attempts = 2;
+        private static readonly TimeSpan PerAttemptTimeout = TimeSpan.FromSeconds(15);
+        private static readonly TimeSpan RetryDelay = TimeSpan.FromSeconds(3);
+        private static readonly TimeSpan Budget = TimeSpan.FromSeconds(40);
+
+        public static void SendBlocking(
+            EmergencyReporter emergencyReporter,
+            AgentErrorType errorType,
+            string message,
+            AgentLogger logger)
+        {
+            if (emergencyReporter == null) return;
+
+            try
+            {
+                emergencyReporter
+                    .TrySendAsync(
+                        errorType,
+                        message,
+                        httpStatusCode: (int)HttpStatusCode.Gone,
+                        attempts: Attempts,
+                        perAttemptTimeout: PerAttemptTimeout,
+                        retryDelay: RetryDelay)
+                    .Wait(Budget);
+            }
+            catch (Exception ex)
+            {
+                logger.Debug($"Session-gone report send failed (best-effort): {ex.Message}");
+            }
+        }
+    }
+}
@@ -13,9 +13,9 @@
  </PropertyGroup>

  <ItemGroup>
-    <PackageReference Include="Microsoft.NET.Test.Sdk" Version="17.11.1" />
-    <PackageReference Include="xunit" Version="2.9.2" />
-    <PackageReference Include="xunit.runner.visualstudio" Version="2.8.2">
+    <PackageReference Include="Microsoft.NET.Test.Sdk" Version="18.11.0" />
+    <PackageReference Include="xunit" Version="2.9.3" />
+    <PackageReference Include="xunit.runner.visualstudio" Version="4.0.1">
      <IncludeAssets>runtime; build; native; contentfiles; analyzers; buildtransitive</IncludeAssets>
      <PrivateAssets>all</PrivateAssets>
    </PackageReference>
@@ -15,9 +15,9 @@
  </PropertyGroup>

  <ItemGroup>
-    <PackageReference Include="Microsoft.NET.Test.Sdk" Version="17.11.1" />
-    <PackageReference Include="xunit" Version="2.9.2" />
-    <PackageReference Include="xunit.runner.visualstudio" Version="2.8.2">
+    <PackageReference Include="Microsoft.NET.Test.Sdk" Version="18.11.0" />
+    <PackageReference Include="xunit" Version="2.9.3" />
+    <PackageReference Include="xunit.runner.visualstudio" Version="4.0.1">
      <IncludeAssets>runtime; build; native; contentfiles; analyzers; buildtransitive</IncludeAssets>
      <PrivateAssets>all</PrivateAssets>
    </PackageReference>
@@ -15,7 +15,7 @@
  </ItemGroup>

  <ItemGroup>
-    <PackageReference Include="Newtonsoft.Json" Version="13.0.3" />
+    <PackageReference Include="Newtonsoft.Json" Version="13.0.4" />
  </ItemGroup>

  <ItemGroup>
@@ -0,0 +1,184 @@
+using AutopilotMonitor.Functions.Functions.Rules;
+using AutopilotMonitor.Functions.Services;
+using AutopilotMonitor.Shared.DataAccess;
+using AutopilotMonitor.Shared.Models;
+using Microsoft.Extensions.Logging.Abstractions;
+using Moq;
+
+namespace AutopilotMonitor.Functions.Tests;
+
+/// <summary>
+/// The size limits of a tenant-authored analyze rule (D-410): at most 20 conditions and 10
+/// preconditions, and every value a regex or not_regex operator compares — condition value,
+/// filter value, event A filter value, precondition value — at most 2,000 characters and
+/// parseable. One implementation feeds the dry-run validation and every write path (create,
+/// update, template copy); the boundary itself is always allowed.
+/// </summary>
+public class AnalyzeRuleShapeLimitsTests
+{
+    private const string TenantId = "tenant-limits";
+
+    [Fact]
+    public void A_rule_at_every_limit_passes()
+    {
+        var rule = Rule(AnalyzeRuleLimits.MaxConditions, AnalyzeRuleLimits.MaxPreconditions);
+        var atLimit = new string('a', AnalyzeRuleLimits.MaxRegexLength);
+        rule.Conditions[0].Operator = "regex";
+        rule.Conditions[0].Value = atLimit;
+        rule.Conditions[1].FilterField = "f";
+        rule.Conditions[1].FilterOperator = "not_regex";
+        rule.Conditions[1].FilterValue = atLimit;
+        rule.Conditions[2].EventAFilterOperator = "REGEX";
+        rule.Conditions[2].EventAFilterValue = atLimit;
+        rule.Preconditions[0].Operator = "regex";
+        rule.Preconditions[0].Value = atLimit;
+
+        Assert.Empty(AnalyzeRuleService.ShapeLimitErrors(rule));
+    }
+
+    [Fact]
+    public void One_condition_or_precondition_over_the_limit_is_named()
+    {
+        var errors = AnalyzeRuleService.ShapeLimitErrors(Rule(AnalyzeRuleLimits.MaxConditions + 1, AnalyzeRuleLimits.MaxPreconditions + 1));
+
+        Assert.Contains(errors, e => e.Contains("at most 20 conditions (this one has 21)"));
+        Assert.Contains(errors, e => e.Contains("at most 10 preconditions (this one has 11)"));
+    }
+
+    [Theory]
+    [InlineData("conditions[0].value")]
+    [InlineData("conditions[0].filterValue")]
+    [InlineData("conditions[0].eventAFilterValue")]
+    [InlineData("preconditions[0].value")]
+    public void A_regex_over_the_length_limit_is_rejected_wherever_it_sits(string field)
+    {
+        var rule = Rule(1, 1);
+        Place(rule, field, "regex", new string('a', AnalyzeRuleLimits.MaxRegexLength + 1));
+
+        var error = Assert.Single(AnalyzeRuleService.ShapeLimitErrors(rule));
+        Assert.StartsWith($"{field}: a regex may be at most 2000 characters (this one has 2001)", error);
+    }
+
+    [Theory]
+    [InlineData("conditions[0].filterValue")]
+    [InlineData("conditions[0].eventAFilterValue")]
+    [InlineData("preconditions[0].value")]
+    public void An_unparseable_regex_is_rejected_beyond_the_condition_value(string field)
+    {
+        var rule = Rule(1, 1);
+        Place(rule, field, "not_regex", "([unclosed");
+
+        var error = Assert.Single(AnalyzeRuleService.ShapeLimitErrors(rule));
+        Assert.StartsWith($"{field}: value is not a valid regex", error);
+    }
+
+    [Fact]
+    public void A_long_value_of_any_other_operator_is_not_limited()
+    {
+        var rule = Rule(1, 0);
+        rule.Conditions[0].Operator = "not_in";
+        rule.Conditions[0].Value = string.Join(",", Enumerable.Range(0, 1000).Select(i => $"app-{i:D5}"));
+
+        Assert.Empty(AnalyzeRuleService.ShapeLimitErrors(rule));
+    }
+
+    [Fact]
+    public void The_dry_run_validation_carries_the_limits()
+    {
+        var rule = Rule(AnalyzeRuleLimits.MaxConditions + 1, 0);
+
+        Assert.Contains(DryRunAnalyzeRuleFunction.ValidateDraftRule(rule), e => e.Contains("at most 20 conditions"));
+    }
+
+    // ===== write paths =====
+
+    [Fact]
+    public async Task Create_rejects_an_oversized_rule_before_anything_is_stored()
+    {
+        var repo = new Mock<IRuleRepository>();
+        var service = new AnalyzeRuleService(repo.Object, NullLogger<AnalyzeRuleService>.Instance);
+
+        await Assert.ThrowsAsync<ArgumentException>(() => service.CreateRuleAsync(TenantId, Rule(AnalyzeRuleLimits.MaxConditions + 1, 0)));
+        repo.Verify(r => r.StoreAnalyzeRuleAsync(It.IsAny<AnalyzeRule>(), It.IsAny<string>()), Times.Never);
+    }
+
+    [Fact]
+    public async Task Update_of_a_custom_rule_rejects_an_oversized_regex_before_anything_is_stored()
+    {
+        var repo = new Mock<IRuleRepository>();
+        var service = new AnalyzeRuleService(repo.Object, NullLogger<AnalyzeRuleService>.Instance);
+        var rule = Rule(1, 0);
+        Place(rule, "conditions[0].value", "not_regex", new string('a', AnalyzeRuleLimits.MaxRegexLength + 1));
+
+        await Assert.ThrowsAsync<ArgumentException>(() => service.UpdateRuleAsync(TenantId, rule));
+        repo.Verify(r => r.StoreAnalyzeRuleAsync(It.IsAny<AnalyzeRule>(), It.IsAny<string>()), Times.Never);
+    }
+
+    [Fact]
+    public async Task Template_copy_rejects_an_oversized_regex_from_its_variable()
+    {
+        // ANALYZE-SEC-006 shape: the template variable IS the tenant's not_regex allow-list.
+        var template = Rule(1, 0);
+        template.RuleId = "ANALYZE-SEC-006";
+        template.IsBuiltIn = true;
+        template.Conditions[0].Operator = "not_regex";
+        template.TemplateVariables = new List<TemplateVariable> { new() { Name = "allowList", ConditionIndex = 0, Field = "value" } };
+
+        var repo = new Mock<IRuleRepository>();
+        repo.Setup(r => r.GetAnalyzeRulesAsync("global")).ReturnsAsync(new List<AnalyzeRule> { template });
+        repo.Setup(r => r.GetAnalyzeRulesAsync(TenantId)).ReturnsAsync(new List<AnalyzeRule>());
+        repo.Setup(r => r.GetRuleStatesAsync(TenantId)).ReturnsAsync(new Dictionary<string, RuleState>());
+        var service = new AnalyzeRuleService(repo.Object, NullLogger<AnalyzeRuleService>.Instance);
+
+        await Assert.ThrowsAsync<ArgumentException>(() => service.CreateFromTemplateAsync(TenantId, "ANALYZE-SEC-006",
+            new Dictionary<string, string> { ["allowList"] = new string('a', AnalyzeRuleLimits.MaxRegexLength + 1) }));
+        repo.Verify(r => r.StoreAnalyzeRuleAsync(It.IsAny<AnalyzeRule>(), TenantId), Times.Never);
+    }
+
+    // ===== fixtures =====
+
+    private static AnalyzeRule Rule(int conditions, int preconditions) => new()
+    {
+        RuleId = "CUSTOM-LIMITS",
+        IsBuiltIn = false, // the model defaults to a built-in rule
+        Title = "limits",
+        Severity = "warning",
+        Category = "test",
+        BaseConfidence = 80,
+        ConfidenceThreshold = 40,
+        Conditions = Enumerable.Range(0, conditions).Select(i => new RuleCondition
+        {
+            Signal = $"s{i}", Source = "event_data", EventType = "app_install_failed", DataField = "errorCode",
+            Operator = "equals", Value = "1", Required = true,
+        }).ToList(),
+        Preconditions = Enumerable.Range(0, preconditions).Select(_ => new RulePrecondition
+        {
+            Source = "event_data", EventType = "os_info", DataField = "edition", Operator = "equals", Value = "Enterprise",
+        }).ToList(),
+    };
+
+    private static void Place(AnalyzeRule rule, string field, string op, string value)
+    {
+        switch (field)
+        {
+            case "conditions[0].value":
+                rule.Conditions[0].Operator = op;
+                rule.Conditions[0].Value = value;
+                break;
+            case "conditions[0].filterValue":
+                rule.Conditions[0].FilterField = "f";
+                rule.Conditions[0].FilterOperator = op;
+                rule.Conditions[0].FilterValue = value;
+                break;
+            case "conditions[0].eventAFilterValue":
+                rule.Conditions[0].EventAFilterField = "f";
+                rule.Conditions[0].EventAFilterOperator = op;
+                rule.Conditions[0].EventAFilterValue = value;
+                break;
+            default:
+                rule.Preconditions[0].Operator = op;
+                rule.Preconditions[0].Value = value;
+                break;
+        }
+    }
+}
@@ -5,6 +5,7 @@ using AutopilotMonitor.Functions.Services.GraphResolution;
 using AutopilotMonitor.Functions.Services.Notifications;
 using AutopilotMonitor.Shared.DataAccess;
 using AutopilotMonitor.Shared.Models;
+using AutopilotMonitor.Shared.Models.Graph;
 using Microsoft.ApplicationInsights;
 using Microsoft.ApplicationInsights.Extensibility;
 using Microsoft.Extensions.Caching.Memory;
@@ -72,7 +73,8 @@ public class AppHomingServiceTests
            Mock.Of<System.Net.Http.IHttpClientFactory>(),
            cache,
            _registry,
-            _tenantConfigMock.Object)
+            _tenantConfigMock.Object,
+            Mock.Of<IGraphAccessHealthRecorder>())
        { CallBase = false };
        _detectorMock = new Mock<IGraphFeatureDetector>();
        _maintenanceMock = new Mock<IMaintenanceRepository>();
@@ -287,6 +289,32 @@ public class AppHomingServiceTests
        Assert.True((await _sut.ProbePrimaryConsentAsync(TenantId)).Succeeded);
    }

+    [Fact]
+    public async Task Probe_succeeds_when_the_budget_cuts_the_retries_of_a_missing_legacy_service_principal()
+    {
+        // The access check runs on 4 s and the first retry waits 5 s, so the answer arrives as
+        // transient. The Entra code still says the SP is gone: nothing left to lose.
+        SetupProbe(GraphTokenResult.Success(Jwt(ValidationRole)));
+        SetupLegacyToken(GraphTokenResult.TransientFailure(
+            new EntraTokenRejection(401, EntraTokenRejection.ServicePrincipalMissingCode, "no service principal")));
+
+        Assert.True((await _sut.ProbePrimaryConsentAsync(TenantId)).Succeeded);
+    }
+
+    [Fact]
+    public async Task Probe_stays_transient_when_the_budget_cuts_the_retries_of_any_other_legacy_rejection()
+    {
+        // Any other refusal proves nothing about the roles the tenant would lose with the flip.
+        SetupProbe(GraphTokenResult.Success(Jwt(ValidationRole)));
+        SetupLegacyToken(GraphTokenResult.TransientFailure(
+            new EntraTokenRejection(400, "AADSTS53003", "blocked by Conditional Access")));
+
+        var probe = await _sut.ProbePrimaryConsentAsync(TenantId);
+
+        Assert.False(probe.Succeeded);
+        Assert.True(probe.IsTransient);
+    }
+
    [Fact]
    public async Task Probe_never_mints_a_legacy_token_when_the_primary_token_fails()
    {
@@ -349,6 +377,43 @@ public class AppHomingServiceTests
        Assert.DoesNotContain(_savedOpsEvents, e => e.EventType == "AppHomingFlippedWithEntraRoles");
    }

+    [Fact]
+    public async Task AutoFlip_clears_the_graph_access_rejection_of_the_app_the_tenant_leaves()
+    {
+        _store.Row!.GraphAccessRejectedSince = DateTime.UtcNow.AddHours(-3);
+        _store.Row.GraphAccessRejectedCode = EntraTokenRejection.ServicePrincipalMissingCode;
+        _store.Row.GraphAccessRejectionConfirmedAt = DateTime.UtcNow.AddHours(-2);
+
+        var outcome = await _sut.TryAutoFlipToPrimaryAsync(LegacyHomedConfig(), Actor);
+
+        Assert.Equal(AppHomingAutoFlipOutcome.Flipped, outcome.Outcome);
+        Assert.Null(_store.Row!.GraphAccessRejectedSince);
+        Assert.Null(_store.Row.GraphAccessRejectedCode);
+        Assert.Null(_store.Row.GraphAccessRejectionConfirmedAt);
+        // The confirmed episode ends visibly: the ops trail never keeps an open rejection.
+        var closed = Assert.Single(_savedOpsEvents, e => e.EventType == OpsEventTypes.GraphAccessRecovered);
+        Assert.Contains("app-homing-flip", closed.Details);
+    }
+
+    [Fact]
+    public async Task AutoFlip_clears_the_addon_episodes_and_closes_only_the_confirmed_ones()
+    {
+        _store.Row!.IntuneDeviceBindingPermissionMissingSince = DateTime.UtcNow.AddHours(-3);
+        _store.Row.IntuneDeviceBindingPermissionMissingConfirmedAt = DateTime.UtcNow.AddHours(-2);
+        _store.Row.CloudPcPermissionMissingSince = DateTime.UtcNow.AddMinutes(-5);
+
+        await _sut.TryAutoFlipToPrimaryAsync(LegacyHomedConfig(), Actor);
+
+        Assert.Null(_store.Row!.IntuneDeviceBindingPermissionMissingSince);
+        Assert.Null(_store.Row.IntuneDeviceBindingPermissionMissingConfirmedAt);
+        Assert.Null(_store.Row.CloudPcPermissionMissingSince);
+        var resolved = Assert.Single(_savedOpsEvents, e => e.EventType == OpsEventTypes.AddOnPermissionResolved);
+        Assert.Contains(GraphFeatureCatalog.FeatureIntuneDeviceBinding, resolved.Details);
+        Assert.Contains(GraphAccessHealthRecorder.ResolvedByAppHomingFlip, resolved.Details);
+        // An unconfirmed rejection was never shown, so it ends without a trace.
+        Assert.DoesNotContain(_savedOpsEvents, e => e.EventType == OpsEventTypes.GraphAccessRecovered);
+    }
+
    [Fact]
    public async Task AutoFlip_does_not_flip_on_permanent_probe_failure()
    {
@@ -2,6 +2,7 @@ using System.Text.Json;
 using AutopilotMonitor.Functions.Functions.Raw;
 using AutopilotMonitor.Functions.Middleware;
 using AutopilotMonitor.Functions.Security;
+using AutopilotMonitor.Functions.Services;
 using Xunit;

 namespace AutopilotMonitor.Functions.Tests;
@@ -71,7 +72,7 @@ public class AppInsightsQueryFunctionTests
            "rows":[["2026-09-04T10:00:00Z",42,"{\"TenantId\":\"t1\"}",null]]}]}
            """;

-        var (tables, partial) = AppInsightsQueryFunction.ParseKustoBody(body);
+        var (tables, partial) = LogQueryExecutor.ParseKustoBody(body);

        Assert.Null(partial);
        var table = Assert.Single(tables);
@@ -97,7 +98,7 @@ public class AppInsightsQueryFunctionTests
             "error":{"code":"PartialError","message":"There were some errors when processing your query.","innererror":{"code":"E_QUERY_RESULT_SET_TOO_LARGE","message":"Query result set has exceeded the internal record count limit 500000."}}}
            """;

-        var (tables, partial) = AppInsightsQueryFunction.ParseKustoBody(body);
+        var (tables, partial) = LogQueryExecutor.ParseKustoBody(body);

        Assert.Single(tables);
        Assert.Equal("E_QUERY_RESULT_SET_TOO_LARGE: Query result set has exceeded the internal record count limit 500000.", partial);
@@ -106,7 +107,7 @@ public class AppInsightsQueryFunctionTests
    [Fact]
    public void Empty_or_shapeless_body_yields_no_tables_and_no_partial()
    {
-        var (tables, partial) = AppInsightsQueryFunction.ParseKustoBody("{}");
+        var (tables, partial) = LogQueryExecutor.ParseKustoBody("{}");
        Assert.Empty(tables);
        Assert.Null(partial);
    }
@@ -115,16 +116,16 @@ public class AppInsightsQueryFunctionTests
    [Fact]
    public void Error_extraction_prefers_innererror_and_tolerates_non_json()
    {
-        var (msg, code) = AppInsightsQueryFunction.ExtractError(
+        var (msg, code) = LogQueryExecutor.ExtractError(
            """{"error":{"message":"The request had some invalid properties","code":"BadArgumentError","innererror":{"code":"SyntaxError","message":"Query could not be parsed at 'foo'"}}}""");
        Assert.Equal("SyntaxError", code);
        Assert.Equal("Query could not be parsed at 'foo'", msg);

-        var (outerMsg, outerCode) = AppInsightsQueryFunction.ExtractError("""{"error":{"message":"Forbidden","code":"InsufficientAccessError"}}""");
+        var (outerMsg, outerCode) = LogQueryExecutor.ExtractError("""{"error":{"message":"Forbidden","code":"InsufficientAccessError"}}""");
        Assert.Equal("InsufficientAccessError", outerCode);
        Assert.Equal("Forbidden", outerMsg);

-        var (plainMsg, plainCode) = AppInsightsQueryFunction.ExtractError("<html>502 Bad Gateway</html>");
+        var (plainMsg, plainCode) = LogQueryExecutor.ExtractError("<html>502 Bad Gateway</html>");
        Assert.Null(plainCode);
        Assert.Equal("Telemetry store query failed", plainMsg);
    }
@@ -0,0 +1,97 @@
+using System;
+using System.Collections.Generic;
+using System.Threading.Tasks;
+using AutopilotMonitor.Functions.Services;
+using AutopilotMonitor.Shared.Models;
+using Xunit;
+
+namespace AutopilotMonitor.Functions.Tests;
+
+/// <summary>
+/// A radar pass reads one tenant at a time so its memory follows the largest tenant, and it never
+/// evaluates an empty list: re-arm would read that as "version drained" and delete open episodes.
+/// </summary>
+public class AppVersionRadarPassTests
+{
+    private static List<AppInstallSummary> Rows(string tenantId, int count)
+    {
+        var rows = new List<AppInstallSummary>();
+        for (var i = 0; i < count; i++)
+            rows.Add(new AppInstallSummary { TenantId = tenantId });
+        return rows;
+    }
+
+    [Fact]
+    public async Task Each_tenant_is_finished_before_the_next_one_is_loaded()
+    {
+        var calls = new List<string>();
+
+        await MaintenanceService.RunAppVersionRadarPassAsync(
+            new[] { "a", "b" },
+            tenantId =>
+            {
+                calls.Add($"load {tenantId}");
+                return Task.FromResult(Rows(tenantId, 2));
+            },
+            (tenantId, summaries) =>
+            {
+                calls.Add($"evaluate {tenantId}");
+                Assert.All(summaries, s => Assert.Equal(tenantId, s.TenantId));
+                return Task.FromResult((0, 0, 0));
+            },
+            (_, ex) => throw ex);
+
+        Assert.Equal(new[] { "load a", "evaluate a", "load b", "evaluate b" }, calls);
+    }
+
+    [Fact]
+    public async Task A_tenant_without_rows_is_not_evaluated()
+    {
+        var evaluated = new List<string>();
+
+        var pass = await MaintenanceService.RunAppVersionRadarPassAsync(
+            new[] { "empty", "full" },
+            tenantId => Task.FromResult(tenantId == "empty" ? new List<AppInstallSummary>() : Rows(tenantId, 3)),
+            (tenantId, _) =>
+            {
+                evaluated.Add(tenantId);
+                return Task.FromResult((0, 0, 0));
+            },
+            (_, ex) => throw ex);
+
+        Assert.Equal(new[] { "full" }, evaluated);
+        Assert.Equal(1, pass.Tenants);
+        Assert.Equal(3, pass.Rows);
+    }
+
+    [Fact]
+    public async Task A_failing_tenant_does_not_cost_the_others_their_pass()
+    {
+        var failed = new List<string>();
+
+        var pass = await MaintenanceService.RunAppVersionRadarPassAsync(
+            new[] { "load-fails", "evaluate-fails", "ok" },
+            tenantId => tenantId == "load-fails"
+                ? throw new InvalidOperationException("load")
+                : Task.FromResult(Rows(tenantId, 1)),
+            (tenantId, _) => tenantId == "evaluate-fails"
+                ? throw new InvalidOperationException("evaluate")
+                : Task.FromResult((1, 2, 3)),
+            (tenantId, _) => failed.Add(tenantId));
+
+        Assert.Equal(new[] { "load-fails", "evaluate-fails" }, failed);
+        Assert.Equal((1, 2, 3), (pass.Fired, pass.Refreshed, pass.Rearmed));
+    }
+
+    [Fact]
+    public async Task The_totals_add_up_over_the_tenants()
+    {
+        var pass = await MaintenanceService.RunAppVersionRadarPassAsync(
+            new[] { "a", "b" },
+            tenantId => Task.FromResult(Rows(tenantId, 2)),
+            (_, _) => Task.FromResult((1, 2, 3)),
+            (_, ex) => throw ex);
+
+        Assert.Equal((2, 4L, 2, 4, 6), pass);
+    }
+}
@@ -35,7 +35,6 @@ public class AuthFunctionSideEffectTests
    private readonly Mock<TenantAdminsService> _tenantAdminsMock;
    private readonly Mock<PreviewWhitelistService> _previewMock;
    private readonly Mock<McpUserService> _mcpUserMock;
-    private readonly Mock<TelegramNotificationService> _telegramMock;
    private readonly Mock<OpsEventService> _opsEventsMock;
    private readonly Mock<GlobalNotificationService> _globalNotificationMock;
    private readonly Mock<IMetricsRepository> _metricsRepoMock;
@@ -84,10 +83,6 @@ public class AuthFunctionSideEffectTests
            configRepo, cache, Mock.Of<ILogger<PreviewWhitelistService>>(), _tenantConfigMock.Object)
        { CallBase = false };

-        _telegramMock = new Mock<TelegramNotificationService>(
-            new HttpClient(), configRepo, Mock.Of<ILogger<TelegramNotificationService>>())
-        { CallBase = false };
-
        _globalNotificationMock = new Mock<GlobalNotificationService>(
            notificationRepo, new FakeSignalRNotificationService(), Mock.Of<ILogger<GlobalNotificationService>>())
        { CallBase = false };
@@ -117,7 +112,6 @@ public class AuthFunctionSideEffectTests
            tenantAdmins ?? _tenantAdminsMock.Object,
            _metricsRepoMock.Object,
            preview ?? _previewMock.Object,
-            _telegramMock.Object,
            _globalNotificationMock.Object,
            _mcpUserMock.Object,
            _autoApproveEnqueuerMock.Object,
@@ -136,9 +130,6 @@ public class AuthFunctionSideEffectTests
        // Writes go through UpdateAsync / CreateOrUpdateAsync over one stored row (none by default:
        // a brand-new tenant). Default: all fire-and-forget calls succeed.
        _store = _tenantConfigMock.StubWrites(TenantId, row: null);
-        _telegramMock
-            .Setup(x => x.SendNewTenantSignupAsync(It.IsAny<string>(), It.IsAny<string>()))
-            .Returns(Task.CompletedTask);
        _globalNotificationMock
            .Setup(x => x.CreateNotificationAsync(
                It.IsAny<string>(), It.IsAny<string>(), It.IsAny<string>(), It.IsAny<string?>()))
@@ -190,7 +181,7 @@ public class AuthFunctionSideEffectTests
        return BuildRequest(new ClaimsPrincipal(new ClaimsIdentity(claims, "test")));
    }

-    private static (HttpRequestData Req, FunctionContext Ctx) BuildRequest(ClaimsPrincipal principal)
+    private static (HttpRequestData Req, FunctionContext Ctx) BuildRequest(ClaimsPrincipal principal, RequestContext? requestContext = null)
    {
        var services = new ServiceCollection();
        services.AddOptions();
@@ -199,9 +190,11 @@ public class AuthFunctionSideEffectTests
                new System.Text.Json.JsonSerializerOptions(System.Text.Json.JsonSerializerDefaults.Web)));
        var provider = services.BuildServiceProvider();

+        var items = new Dictionary<object, object> { ["ClaimsPrincipal"] = principal };
+        if (requestContext != null)
+            items[RequestContext.ItemsKey] = requestContext;
        var context = new Mock<FunctionContext>();
-        context.SetupGet(c => c.Items).Returns(
-            new Dictionary<object, object> { ["ClaimsPrincipal"] = principal });
+        context.SetupGet(c => c.Items).Returns(items);
        context.SetupGet(c => c.InstanceServices).Returns(provider);

        var req = new Mock<HttpRequestData>(context.Object);
@@ -233,7 +226,7 @@ public class AuthFunctionSideEffectTests
        Assert.True(string.IsNullOrEmpty(config.DomainName));
        Assert.Null(config.OnboardedBy);
        Assert.Empty(_store.Writes);
-        _telegramMock.Verify(x => x.SendNewTenantSignupAsync(It.IsAny<string>(), It.IsAny<string>()), Times.Never);
+        _opsEventsMock.Verify(x => x.RecordTenantSignupAsync(It.IsAny<string>(), It.IsAny<string>()), Times.Never);
    }

    [Fact]
@@ -261,8 +254,7 @@ public class AuthFunctionSideEffectTests
        Assert.Null(written.DpaAcceptedBy);
        Assert.Null(written.DpaAcceptedAt);
        Assert.Equal("auth", source);
-        _telegramMock.Verify(x => x.SendNewTenantSignupAsync(TenantId, Upn), Times.Once);
-        _opsEventsMock.Verify(x => x.RecordTenantSignupAsync(TenantId, Upn), Times.Once);   // the routable record next to the ping
+        _opsEventsMock.Verify(x => x.RecordTenantSignupAsync(TenantId, Upn), Times.Once);   // the routable record
        _globalNotificationMock.Verify(x => x.CreateNotificationAsync(
            "preview_signup", "New Tenant Signup",
            It.Is<string>(m => m.Contains(TenantId) && m.Contains("contoso.com") && m.Contains(Upn)),
@@ -350,7 +342,7 @@ public class AuthFunctionSideEffectTests
        Assert.True(string.IsNullOrEmpty(config.DomainName));
        Assert.Null(config.OnboardedBy);
        Assert.Empty(_store.Writes);
-        _telegramMock.Verify(x => x.SendNewTenantSignupAsync(It.IsAny<string>(), It.IsAny<string>()), Times.Never);
+        _opsEventsMock.Verify(x => x.RecordTenantSignupAsync(It.IsAny<string>(), It.IsAny<string>()), Times.Never);
        _autoApproveEnqueuerMock.Verify(x => x.EnqueueAsync(
            It.IsAny<AutopilotMonitor.Functions.Services.Activation.TenantAutoApproveEnvelope>(),
            It.IsAny<TimeSpan?>(), It.IsAny<CancellationToken>()), Times.Never);
@@ -371,7 +363,7 @@ public class AuthFunctionSideEffectTests

        Assert.Empty(_store.Writes);
        Assert.Equal("first@contoso.com", _store.Row!.OnboardedBy);
-        _telegramMock.Verify(x => x.SendNewTenantSignupAsync(It.IsAny<string>(), It.IsAny<string>()), Times.Never);
+        _opsEventsMock.Verify(x => x.RecordTenantSignupAsync(It.IsAny<string>(), It.IsAny<string>()), Times.Never);
        _autoApproveEnqueuerMock.Verify(x => x.EnqueueAsync(
            It.IsAny<AutopilotMonitor.Functions.Services.Activation.TenantAutoApproveEnvelope>(),
            It.IsAny<TimeSpan?>(), It.IsAny<CancellationToken>()), Times.Never);
@@ -389,7 +381,7 @@ public class AuthFunctionSideEffectTests
        await _sut.HandleNewTenantDomainAsync(DefaultConfig(), TenantId, Upn);

        Assert.Empty(_store.Writes);
-        _telegramMock.Verify(x => x.SendNewTenantSignupAsync(It.IsAny<string>(), It.IsAny<string>()), Times.Never);
+        _opsEventsMock.Verify(x => x.RecordTenantSignupAsync(It.IsAny<string>(), It.IsAny<string>()), Times.Never);
    }

    // -------------------------------------------------------------------------
@@ -624,7 +616,7 @@ public class AuthFunctionSideEffectTests
        await _sut.HandleNewTenantDomainAsync(config, TenantId, Upn);

        Assert.Empty(_store.Writes);
-        _telegramMock.Verify(x => x.SendNewTenantSignupAsync(It.IsAny<string>(), It.IsAny<string>()), Times.Never);
+        _opsEventsMock.Verify(x => x.RecordTenantSignupAsync(It.IsAny<string>(), It.IsAny<string>()), Times.Never);
    }

    [Fact]
@@ -650,16 +642,17 @@ public class AuthFunctionSideEffectTests
    }

    [Fact]
-    public async Task HandleNewTenantDomain_TelegramFailure_DoesNotThrow()
+    public async Task HandleNewTenantDomain_BellFailure_DoesNotThrow()
    {
        var config = DefaultConfig();
        config.DomainName = null!;

-        _telegramMock
-            .Setup(x => x.SendNewTenantSignupAsync(It.IsAny<string>(), It.IsAny<string>()))
-            .ThrowsAsync(new HttpRequestException("Telegram unreachable"));
+        _globalNotificationMock
+            .Setup(x => x.CreateNotificationAsync(
+                It.IsAny<string>(), It.IsAny<string>(), It.IsAny<string>(), It.IsAny<string?>()))
+            .ThrowsAsync(new HttpRequestException("Notification store unreachable"));

-        // Should not throw — Telegram is fire-and-forget
+        // Should not throw — the bell is fire-and-forget
        await _sut.HandleNewTenantDomainAsync(config, TenantId, Upn);

        // The write still landed before the fire-and-forget
@@ -1102,4 +1095,96 @@ public class AuthFunctionSideEffectTests
        Assert.Equal(HttpStatusCode.OK, response.StatusCode);
        Assert.Equal(Constants.Push.DeviceStatus.Active, push.Repo.Devices[(Constants.Push.PlatformScope, "ga-phone")].Status);
    }
+
+    // -------------------------------------------------------------------------
+    // GetCurrentUser under view-as: a Global Admin reads another tenant as its member
+    // -------------------------------------------------------------------------
+
+    private const string ViewedTenantId = "cccccccc-1111-2222-3333-444444444444";
+
+    /// <summary>The context PolicyEnforcementMiddleware builds for an admitted view-as request.</summary>
+    private static RequestContext ViewingAs(string role) => new()
+    {
+        TenantId = ViewedTenantId,
+        TargetTenantId = ViewedTenantId,
+        UserPrincipalName = Upn,
+        UserRole = role,
+        IsTenantAdmin = role == Constants.TenantRoles.Admin,
+        ViewAs = new ViewAsContext(TenantId, role),
+    };
+
+    [Fact]
+    public async Task GetCurrentUser_ViewAs_AnswersAsTheViewedTenantsMember_WithoutAnySignInSideEffect()
+    {
+        // The viewed tenant asks for the Terms + DPA; the caller's home row still lacks its domain — exactly the
+        // state in which an ordinary sign-in would seed it, onboard, and record a login.
+        var viewed = TenantConfiguration.CreateDefault(ViewedTenantId);
+        viewed.DomainName = "fabrikam.example";
+        viewed.CompanyName = "Fabrikam";
+        viewed.DpaAcceptancePending = true;
+        var home = DefaultConfig();
+        home.DomainName = null!;
+        _tenantConfigMock.Setup(x => x.TryGetConfigurationAsync(ViewedTenantId)).ReturnsAsync((viewed, true));
+        _tenantConfigMock.Setup(x => x.TryGetConfigurationAsync(TenantId)).ReturnsAsync((home, true));
+        var viewedStore = _tenantConfigMock.StubWrites(ViewedTenantId, row: viewed);
+        _previewMock.Setup(x => x.IsApprovedAsync(ViewedTenantId)).ReturnsAsync(true);
+        _mcpUserMock
+            .Setup(x => x.IsAllowedAsync(It.IsAny<string?>(), It.IsAny<string?>(), It.IsAny<string?>(),
+                It.IsAny<IReadOnlyList<string>?>(), It.IsAny<bool>()))
+            .ReturnsAsync(McpAccessCheckResult.Denied("not allowed"));
+        var seen = new DateTime(2026, 11, 1, 0, 0, 0, DateTimeKind.Utc);
+        _metricsRepoMock.Setup(x => x.GetUserWhatsNewSeenAsync(TenantId, Upn)).ReturnsAsync(new UserWhatsNewSeen(platformUtc: seen));
+        var (req, ctx) = BuildRequest(SignedIn(external: false), ViewingAs(Constants.TenantRoles.Viewer));
+
+        var response = await _sut.GetCurrentUser(req, ctx);
+
+        Assert.Equal(HttpStatusCode.OK, response.StatusCode);
+        var body = await ReadBodyAsync(response);
+        Assert.Contains($"\"tenantId\":\"{ViewedTenantId}\"", body);
+        Assert.Contains("\"isGlobalAdmin\":false", body);
+        Assert.Contains("\"isGlobalReader\":false", body);
+        Assert.Contains("\"isDelegated\":false", body);
+        Assert.Contains("\"role\":\"Viewer\"", body);
+        Assert.Contains("\"isTenantAdmin\":false", body);
+        Assert.Contains("\"dpaAcceptancePending\":true", body);
+        Assert.Contains("\"whatsNewSeenPlatformUtc\":\"2026-11-01T00:00:00Z\"", body);
+        Assert.Contains(
+            $"\"viewAs\":{{\"tenantId\":\"{ViewedTenantId}\",\"tenantName\":\"Fabrikam\",\"role\":\"Viewer\",\"homeTenantId\":\"{TenantId}\"}}",
+            body);
+
+        // No sign-in side effect in either tenant, and no role lookup of the caller at all.
+        Assert.Empty(_store.Writes);
+        Assert.Empty(viewedStore.Writes);
+        _opsEventsMock.Verify(x => x.RecordTenantSignupAsync(It.IsAny<string>(), It.IsAny<string>()), Times.Never);
+        _autoApproveEnqueuerMock.Verify(x => x.EnqueueAsync(
+            It.IsAny<AutopilotMonitor.Functions.Services.Activation.TenantAutoApproveEnvelope>(),
+            It.IsAny<TimeSpan?>(), It.IsAny<CancellationToken>()), Times.Never);
+        _tenantAdminsMock.Verify(x => x.TryAddTenantAdminAsync(It.IsAny<string>(), It.IsAny<string>(), It.IsAny<string>()), Times.Never);
+        _tenantAdminsMock.Verify(x => x.GetMembershipSnapshotAsync(It.IsAny<string>(), It.IsAny<string>()), Times.Never);
+        _metricsRepoMock.Verify(x => x.RecordUserLoginAsync(
+            It.IsAny<string>(), It.IsAny<string>(), It.IsAny<string?>(), It.IsAny<string?>()), Times.Never);
+        _globalAdminMock.Verify(x => x.GetGlobalRoleAsync(It.IsAny<AdminIdentity?>()), Times.Never);
+    }
+
+    [Fact]
+    public async Task GetCurrentUser_ViewAs_AnInactiveTenant_ShowsItsActivationGate()
+    {
+        var viewed = TenantConfiguration.CreateDefault(ViewedTenantId);
+        viewed.DomainName = "fabrikam.example";
+        _tenantConfigMock.Setup(x => x.TryGetConfigurationAsync(ViewedTenantId)).ReturnsAsync((viewed, true));
+        _tenantConfigMock.Setup(x => x.TryGetConfigurationAsync(TenantId)).ReturnsAsync((DefaultConfig(), true));
+        _previewMock.Setup(x => x.IsApprovedAsync(ViewedTenantId)).ReturnsAsync(false);
+        _mcpUserMock
+            .Setup(x => x.IsAllowedAsync(It.IsAny<string?>(), It.IsAny<string?>(), It.IsAny<string?>(),
+                It.IsAny<IReadOnlyList<string>?>(), It.IsAny<bool>()))
+            .ReturnsAsync(McpAccessCheckResult.Denied("not allowed"));
+        _metricsRepoMock.Setup(x => x.GetUserWhatsNewSeenAsync(TenantId, Upn)).ReturnsAsync(new UserWhatsNewSeen());
+        var (req, ctx) = BuildRequest(SignedIn(external: false), ViewingAs(Constants.TenantRoles.Admin));
+
+        var response = await _sut.GetCurrentUser(req, ctx);
+
+        // What the tenant's own admin gets while the tenant waits for activation — the Global Admin bypass is gone.
+        Assert.Equal(HttpStatusCode.Forbidden, response.StatusCode);
+        Assert.Contains("PendingActivation", await ReadBodyAsync(response));
+    }
 }
@@ -93,6 +93,39 @@ public class AuthFunctionTests
        Assert.Equal(pending, (bool)ToDynamic(result.Body).dpaAcceptancePending);
    }

+    [Fact]
+    public void HappyPath_MemberWithARoleGetsTheCompanyName()
+    {
+        var config = DefaultConfig();
+        config.CompanyName = "  Contoso Ltd.  ";
+
+        var result = AuthFunction.BuildAuthResult(
+            config, isGlobalAdmin: false, isGlobalReader: false, isPreviewApproved: true,
+            memberRole: ViewerRole(), mcpCheck: McpAllowed(),
+            hasTenantAdmins: true,
+            TenantId, Upn, DisplayName, ObjectId);
+
+        Assert.True(result.IsSuccess);
+        Assert.Equal("Contoso Ltd.", (string)ToDynamic(result.Body).companyName);
+    }
+
+    [Fact]
+    public void HappyPath_RolelessMemberGetsNoCompanyName()
+    {
+        // Without a role the caller sees only the Progress Portal; the config GET would refuse them.
+        var config = DefaultConfig();
+        config.CompanyName = "Contoso Ltd.";
+
+        var result = AuthFunction.BuildAuthResult(
+            config, isGlobalAdmin: false, isGlobalReader: false, isPreviewApproved: true,
+            memberRole: null, mcpCheck: McpAllowed(),
+            hasTenantAdmins: true,
+            TenantId, Upn, DisplayName, ObjectId);
+
+        Assert.True(result.IsSuccess);
+        Assert.Null((string?)ToDynamic(result.Body).companyName);
+    }
+
    [Theory]
    [InlineData("platform", "platform")]
    [InlineData("Platform", "platform")]
@@ -1,4 +1,5 @@
 using System.Net;
+using System.Text.Json;
 using AutopilotMonitor.Functions.Security;
 using AutopilotMonitor.Shared.DataAccess;
 using AutopilotMonitor.Functions.Services;
@@ -69,7 +70,7 @@ public class AutopilotDeviceValidatorTests
            Mock.Of<IConfigRepository>(), NullLogger<TenantConfigurationService>.Instance, cache)
        { CallBase = false };
        var tokenService = new Mock<GraphTokenService>(
-            NullLogger<GraphTokenService>.Instance, Mock.Of<IHttpClientFactory>(), cache, registry, tenantConfig.Object)
+            NullLogger<GraphTokenService>.Instance, Mock.Of<IHttpClientFactory>(), cache, registry, tenantConfig.Object, Mock.Of<IGraphAccessHealthRecorder>())
        { CallBase = false };
        tokenService.Setup(t => t.GetAccessTokenAsync(TenantId, It.IsAny<CancellationToken>()))
            .ReturnsAsync(GraphTokenResult.Success("token"));
@@ -95,7 +96,7 @@ public class AutopilotDeviceValidatorTests
        var result = await sut.ValidateAutopilotDeviceAsync(TenantId, Serial, null, CancellationToken.None);

        Assert.True(result.IsValid);
-        Assert.Equal("ap-1", result.AutopilotDeviceId);
+        Assert.Equal("ap-1", result.Registration!.DeviceId);
        Assert.Equal(2, handler.Requests.Count);
        tokens.Verify(t => t.InvalidateTenant(TenantId), Times.Once);
        tokens.Verify(t => t.GetAccessTokenAsync(TenantId, It.IsAny<CancellationToken>()), Times.Exactly(2));
@@ -168,7 +169,7 @@ public class AutopilotDeviceValidatorTests
        var result = await sut.ValidateAutopilotDeviceAsync(TenantId, Serial, null, CancellationToken.None);

        Assert.True(result.IsValid);
-        Assert.Equal("ap-1", result.AutopilotDeviceId);
+        Assert.Equal("ap-1", result.Registration!.DeviceId);
        Assert.Equal(2, handler.Requests.Count);
    }

@@ -201,7 +202,7 @@ public class AutopilotDeviceValidatorTests
            Mock.Of<IConfigRepository>(), NullLogger<TenantConfigurationService>.Instance, cache)
        { CallBase = false };
        var tokenService = new Mock<GraphTokenService>(
-            NullLogger<GraphTokenService>.Instance, Mock.Of<IHttpClientFactory>(), cache, registry, tenantConfig.Object)
+            NullLogger<GraphTokenService>.Instance, Mock.Of<IHttpClientFactory>(), cache, registry, tenantConfig.Object, Mock.Of<IGraphAccessHealthRecorder>())
        { CallBase = false };
        CancellationToken observed = default;
        tokenService.Setup(t => t.GetAccessTokenAsync(TenantId, It.IsAny<CancellationToken>()))
@@ -213,4 +214,66 @@ public class AutopilotDeviceValidatorTests

        Assert.True(observed.CanBeCanceled);
    }
+
+    // ── Registration fields the session keeps ────────────────────────────────
+
+    private const string Upn = "first.last@example.invalid";
+
+    private static JsonElement Device(string json) => JsonSerializer.Deserialize<JsonElement>(json);
+
+    [Fact]
+    public void ReadRegistration_MapsTheKeptFields_AndKeepsOnlyWhetherAUserIsAssigned()
+    {
+        var device = Device(
+            "{\"id\":\"ap-1\",\"groupTag\":\" TEST \",\"purchaseOrderIdentifier\":\"PO-7\",\"displayName\":\"LAB-01\"," +
+            $"\"userPrincipalName\":\"{Upn}\",\"addressableUserName\":\"First Last\",\"productKey\":\"AAAAA-BBBBB\"}}");
+
+        var registration = AutopilotDeviceValidator.ReadRegistration(device);
+
+        Assert.Equal("ap-1", registration.DeviceId);
+        Assert.Equal("TEST", registration.GroupTag);
+        Assert.Equal("PO-7", registration.PurchaseOrderId);
+        Assert.Equal("LAB-01", registration.DisplayName);
+        Assert.True(registration.UserAssigned);
+        var kept = Newtonsoft.Json.JsonConvert.SerializeObject(registration);
+        Assert.DoesNotContain(Upn, kept);
+        Assert.DoesNotContain("First Last", kept);
+        Assert.DoesNotContain("AAAAA-BBBBB", kept);
+    }
+
+    [Fact]
+    public void ReadRegistration_TreatsBlankMissingAndNonTextValuesAsAbsent()
+    {
+        var device = Device(
+            "{\"id\":\"ap-1\",\"groupTag\":\"   \",\"purchaseOrderIdentifier\":null,\"displayName\":42,\"userPrincipalName\":\"\"}");
+
+        var registration = AutopilotDeviceValidator.ReadRegistration(device);
+
+        Assert.Null(registration.GroupTag);
+        Assert.Null(registration.PurchaseOrderId);
+        Assert.Null(registration.DisplayName);
+        Assert.False(registration.UserAssigned);
+    }
+
+    [Fact]
+    public void ReadRegistration_CutsOverlongText()
+    {
+        var longTag = new string('x', AutopilotDeviceValidator.MaxRegistrationFieldLength + 50);
+        var device = Device($"{{\"id\":\"ap-1\",\"groupTag\":\"{longTag}\"}}");
+
+        Assert.Equal(AutopilotDeviceValidator.MaxRegistrationFieldLength, AutopilotDeviceValidator.ReadRegistration(device).GroupTag!.Length);
+    }
+
+    [Fact]
+    public async Task CachedValidation_CarriesTheRegistration()
+    {
+        var (sut, handler, _) = BuildSut(Json(
+            "{\"value\":[{\"id\":\"ap-1\",\"serialNumber\":\"PF3XKQ7\",\"groupTag\":\"TEST\"}]}"));
+
+        await sut.ValidateAutopilotDeviceAsync(TenantId, Serial, null, CancellationToken.None);
+        var cached = await sut.ValidateAutopilotDeviceAsync(TenantId, Serial, null, CancellationToken.None);
+
+        Assert.Single(handler.Requests);
+        Assert.Equal("TEST", cached.Registration!.GroupTag);
+    }
 }
--- a/Show More
+++ b/Show More