distress: carry the W365 Cloud PC marker into Devices Not Registered

First W365 field run: the rejected Cloud PC appeared in the report as an
anonymous "Microsoft Corporation / Virtual Machine" row — nothing told the
admin that the fix is the Cloud PC validator, not an Autopilot-registration
hunt. The agent's CloudPcDetector verdict (Windows365 key AND
CloudManagedDesktopExtension service) now rides the pre-auth distress channel:

- Agent: DistressReporter captures isCloudPc at construction (optional ctor
  arg, test fakes stay source-compatible); BackendClientFactory feeds it from
  CloudPcDetector; DistressReport.IsCloudPc on the wire (~18 bytes, fits the
  1536-byte payload cap without a bump — comment updated)
- Backend: DistressReportEntry.IsCloudPc, table column + read mapping
  (legacy rows -> false), structured log + AgentDistressReport AI event key;
  GetDeviceNotRegisteredFunction aggregates sticky-true per serial (same OR
  semantics as the Sessions IsCloudPc merge) and the data-quality notice
  names the new self-reported field. GA global/distress-reports serializes
  the full entry and picks it up automatically.
- Web: Cloud PC badge in the Devices Not Registered table (same sky badge as
  the session table) + conditional hint pointing at the Windows 365 Cloud PC
  Validation toggle and the W365CloudPcValidation Graph add-on.
- Tests: sticky-true + no-marker aggregation cases; MakeEntry helper gains
  the optional flag. Docs: third transport rail in
  backend/cloudpc-device-validation.md + log entry.

Unverified like every distress field — triage context only, never an auth
input. Verified: web tsc clean, eslint 0 errors (file's single warning
pre-exists). .NET build/tests run in CI (no SDK in this sandbox).

Co-Authored-By: Claude Fable 5 <noreply@anthropic.com>
Claude-Session: https://claude.ai/code/session_01RqEFrcAHhWgCvgJgHGzMuv

.github/workflows/build-agent.yml

@@ -194,8 +194,8 @@ jobs:
           # Dev variant = literal-string substitution of the two URL/manifest defaults.
           # Both are uploaded only on -PublishAsStable runs (versioned namespace doesn't carry bootstrap).
           if ('${{ inputs.publish_as_stable }}' -eq 'true') {
-            $stableUrl = '$AgentDownloadUrl = "https://autopilotmonitor.blob.core.windows.net/agent/AutopilotMonitor-Agent.zip"'
-            $devUrl    = '$AgentDownloadUrl = "https://autopilotmonitor.blob.core.windows.net/agent/AutopilotMonitor-Agent-dev.zip"'
+            $stableUrl = '$AgentDownloadUrl = "https://download.autopilotmonitor.com/agent/AutopilotMonitor-Agent.zip"'
+            $devUrl    = '$AgentDownloadUrl = "https://download.autopilotmonitor.com/agent/AutopilotMonitor-Agent-dev.zip"'
             $stableMan = '$VersionJsonName = "version.json"'
             $devMan    = '$VersionJsonName = "version-dev.json"'
 

.github/workflows/ci.yml

@@ -69,9 +69,21 @@ jobs:
 
       - run: npm ci
 
+      # 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
+
       - name: Typecheck
         run: npx tsc --noEmit
 
+      # Errors fail outright. Warnings are ratcheted: the cap is the current
+      # count of accepted warnings (React-Compiler hooks-rule findings demoted
+      # in eslint.config.mjs + exhaustive-deps) — when you fix warnings, lower
+      # the cap to match; never raise it.
+      - name: Lint
+        run: npm run lint -- --max-warnings 99
+
       - name: Tests
         run: npm test
 

.github/workflows/codeql.yml

@@ -57,7 +57,7 @@ jobs:
           dotnet-version: '10.0.x'
 
       - name: Initialize CodeQL
-        uses: github/codeql-action/init@v4
+        uses: github/codeql-action/init@v4.37.3
         with:
           languages: ${{ matrix.language }}
           build-mode: ${{ matrix.build-mode }}
@@ -68,6 +68,6 @@ jobs:
         run: dotnet build AutopilotMonitor.sln --configuration Release
 
       - name: Analyze
-        uses: github/codeql-action/analyze@v4
+        uses: github/codeql-action/analyze@v4.37.3
         with:
           category: /language:${{ matrix.language }}

.github/workflows/deploy-web.yml

@@ -39,6 +39,10 @@ jobs:
         uses: Azure/static-web-apps-deploy@v1
         env:
           NEXT_PUBLIC_ENTRA_CLIENT_ID: ${{ vars.NEXT_PUBLIC_ENTRA_CLIENT_ID }}
+          # Dual app-reg window: previous app registration (unset = single-app behaviour)
+          # and the default app for browsers without a stored selection (legacy|primary).
+          NEXT_PUBLIC_ENTRA_LEGACY_CLIENT_ID: ${{ vars.NEXT_PUBLIC_ENTRA_LEGACY_CLIENT_ID }}
+          NEXT_PUBLIC_ENTRA_DEFAULT_APP: ${{ vars.NEXT_PUBLIC_ENTRA_DEFAULT_APP }}
           NEXT_PUBLIC_ENTRA_REDIRECT_URI: ${{ vars.NEXT_PUBLIC_ENTRA_REDIRECT_URI }}
           NEXT_PUBLIC_ENTRA_POST_LOGOUT_REDIRECT_URI: ${{ vars.NEXT_PUBLIC_ENTRA_POST_LOGOUT_REDIRECT_URI }}
           NEXT_PUBLIC_API_BASE_URL: ${{ vars.NEXT_PUBLIC_API_BASE_URL }}
@@ -52,7 +56,12 @@ jobs:
           # For more information regarding Static Web App workflow configurations, please visit: https://aka.ms/swaworkflowconfig
           app_location: "src/Web/autopilot-monitor-web" # App source code path
           api_location: "" # Api source code path - optional
-          output_location: "" # Built app content directory - optional
+          # Static export (next.config output:'export'): Oryx runs `npm run build`
+          # and uploads the exported out/ directory as plain static files — no
+          # managed SSR runtime is provisioned anymore. (No is_static_export
+          # input on this action version; Oryx detects the export from
+          # next.config + output_location.)
+          output_location: "out" # Built app content directory - optional
           ###### End of Repository/Build Configurations ######
 
   close_pull_request_job:

.github/workflows/pester.yml

@@ -0,0 +1,61 @@
+name: Pester (Bootstrap scripts)
+
+# Runs the Pester suite for the Intune bootstrap scripts under Windows PowerShell 5.1
+# (the runtime IME uses to execute platform scripts) so guard/relax logic changes are
+# verified without resetting a device. Like ci.yml it reports rather than blocks.
+
+on:
+  push:
+    branches: [main]
+    paths: ['scripts/Bootstrap/**']
+  pull_request:
+    branches: [main]
+    paths: ['scripts/Bootstrap/**']
+  workflow_dispatch:
+
+permissions:
+  contents: read
+
+concurrency:
+  group: pester-${{ github.ref }}
+  cancel-in-progress: true
+
+jobs:
+  pester:
+    name: Bootstrap guard tests (PS 5.1)
+    runs-on: windows-latest
+    steps:
+      - uses: actions/checkout@v7
+
+      - name: Install Pester 5+
+        shell: powershell
+        run: |
+          Install-PackageProvider -Name NuGet -MinimumVersion 2.8.5.201 -Force -Scope CurrentUser | Out-Null
+          Install-Module Pester -Scope CurrentUser -Force -SkipPublisherCheck -MinimumVersion 5.5.0
+
+      - name: Run Pester
+        shell: powershell
+        run: |
+          Import-Module Pester -MinimumVersion 5.5.0
+          $c = New-PesterConfiguration
+          $c.Run.Path = 'scripts/Bootstrap'
+          $c.Run.Exit = $true
+          $c.Output.Verbosity = 'Detailed'
+          Invoke-Pester -Configuration $c
+
+      - name: Guard scripts stay pure ASCII
+        shell: powershell
+        run: |
+          $failed = $false
+          Get-ChildItem 'scripts/Bootstrap' -Filter '*.ps1' | ForEach-Object {
+            $bytes = [System.IO.File]::ReadAllBytes($_.FullName)
+            for ($i = 0; $i -lt $bytes.Length; $i++) {
+              if ($bytes[$i] -gt 127) {
+                Write-Host "::error file=scripts/Bootstrap/$($_.Name)::Non-ASCII byte 0x$('{0:X2}' -f $bytes[$i]) at offset $i. PS 5.1 (IME) reads BOM-less files as ANSI and corrupts multi-byte chars."
+                $failed = $true
+                break
+              }
+            }
+          }
+          if ($failed) { exit 1 }
+          Write-Host 'All bootstrap scripts are pure ASCII.'

.gitignore

@@ -53,6 +53,9 @@ __azurite_db*__.json
 node_modules/
 .next/
 out/
+# Managed by Next.js since v16 (regenerated by next dev/build/typegen; path
+# inside flips between .next/types and .next/dev/types) — must not be tracked.
+next-env.d.ts
 build/
 dist/
 !rules/dist/
@@ -148,3 +151,6 @@ plans/REFACTOR_AGENT_V2.md
 scripts/Backup/setup-backup-container.ps1
 docs/Introduction-AutopilotMonitor.pptx
 docs/~$Introduction-AutopilotMonitor.pptx
+
+# Playwright MCP browser artifacts (snapshots, screenshots, console logs)
+.playwright-mcp/

.mcp.json

@@ -3,6 +3,10 @@
     "autopilot-monitor": {
       "type": "http",
       "url": "https://mcp.autopilotmonitor.com/mcp"
+    },
+    "playwright": {
+      "command": "cmd",
+      "args": ["/c", "npx", "@playwright/mcp@latest"]
     }
   }
 }

README.md

@@ -1,14 +1,14 @@
 # <img src="docs/images/logo.svg" height="28" alt="" /> AutopilotMonitor
 
-[![Status](https://img.shields.io/badge/status-Private%20Preview-orange)](https://www.autopilotmonitor.com)
+[![Status](https://img.shields.io/badge/status-live-brightgreen)](https://www.autopilotmonitor.com)
 [![License](https://img.shields.io/badge/license-MIT%20%2B%20AGPL--3.0-blue)](LICENSE)
 [![Website](https://img.shields.io/badge/website-autopilotmonitor.com-2ea44f)](https://www.autopilotmonitor.com)
 
 Advanced monitoring and troubleshooting solution for Windows Autopilot deployments. Gain full visibility into every enrollment session with a detailed event timeline, fleet health dashboards, and session reporting. Define custom analysis rules to automatically detect issues and gather rules to collect targeted evidence. Retrieve diagnostics packages on demand, configure agent settings like auto-reboot behavior and automatic timezone adjustment — all managed centrally from the web dashboard.
 
-## Private Preview
+## Availability
 
-Autopilot Monitor is currently running as a **Private Preview**. Visit **[autopilotmonitor.com](https://www.autopilotmonitor.com)** to request access and learn more.
+Autopilot Monitor is **publicly available** — the Community plan is free. Sign in with your work account at **[autopilotmonitor.com](https://www.autopilotmonitor.com)**; new organizations complete a short activation step after first sign-in.
 
 <p align="center">
   <img src="docs/images/SessionList.png" width="45%" />

docs/agent/autopilot-ztd-diagnostics.md

@@ -119,6 +119,19 @@ normal IME deployment flow. Spam containment, in order:
    payload; the event's own timestamp is the emission time, so the session's `StartedAt`
    (which the backend aligns to the earliest event) is not dragged backwards.
 
+Presentation (2026-07-28, customer feedback — an unannounced wall of pre-agent Error
+events read like a live failure):
+
+- The scan buffers the (capped) record set, first emits an **Info summary event**
+  (`modern_deployment_log`, payload `backfillSummary: true` + `replayedCount` /
+  `droppedOverCap` / `lookbackMinutes`) announcing the replay block, then replays the
+  records **oldest-first** so the timeline sequence follows event-log chronology.
+- The web timeline (`EventTimeline.tsx`) badges `backfilled: true` events („⟲ Backfilled",
+  slate, explanatory tooltip) and renders the original `timeCreated` as the row time with a
+  "(reported …)" suffix; the expanded metadata block gains a `Recorded` line. Severity is
+  deliberately **not** downgraded — unresolved pre-agent errors must still surface in the
+  Error filter.
+
 # Schema — Error codes (backend known-issue map)
 
 Codes documented in the known-issues / troubleshooting-FAQ pages that appear in ESP/enrollment

docs/agent/gather-rule-debug-log.md

@@ -0,0 +1,126 @@
+---
+type: Concept
+title: Gather Rule Debug Log — the per-tenant evaluation trace for rules that produce nothing
+description: EnableGatherRuleDebugLog (ConfigVersion 36) makes the agent write a local trace file explaining every gather-rule evaluation decision — scope skips, missing intervalSeconds, on_change suppression, empty collector results, logparser position/parse-mode/no-match outcomes — so customers can self-diagnose rules that never show up in the timeline.
+resource: /src/Agent/AutopilotMonitor.Agent.V2.Core/Monitoring/Telemetry/Gather/GatherRuleDebugLog.cs
+tags:
+  - agent
+  - gather-rules
+  - diagnostics
+  - tenant-configuration
+timestamp: 2026-07-28T00:00:00+02:00
+---
+
+# Gather Rule Debug Log
+
+## Schema
+
+### The problem
+
+A gather rule that produces no timeline events is indistinguishable from a rule that
+never ran. The pipeline has many *silent-nothing* exits — before this feature, none of
+them were visible to the customer:
+
+| # | Decision point | Where |
+|---|---|---|
+| 1 | Rule delivered but `Enabled=false` | `GatherRuleExecutor.UpdateRules` |
+| 2 | `trigger=interval` without `intervalSeconds` — never runs | `UpdateRules` timer filter |
+| 3 | Interval timer's first tick comes only after one **full** interval | `UpdateRules` timer creation |
+| 4 | Out of phase scope (`activePhases` / `activeFromPhase` not latched); incl. `currentPhase=Unknown` before the first phase signal | `IsRuleInScopeLocked` |
+| 5 | phase_change / phase_exit dedup — once per (rule, phase) | `OnPhaseChanged` |
+| 6 | Collector returned an **empty** result (e.g. `emitOnlyIfExists=true` and target absent) | `ExecuteRule` |
+| 7 | `emit_mode=on_change` — result hash unchanged, emit suppressed | `ShouldEmitOnChange` |
+| 8 | Guard blocked the target (emits `security_warning`, but the rule yields no data) | `GatherRuleContext.EmitSecurityWarning` |
+| 9 | logparser: no files matched, position tracker says nothing new, regex no-match, plain-text file parsed in default `cmtrace` mode, `maxLines` cap, wildcard capped at 20 files | `LogParserCollector` |
+| 10 | Rule execution threw (agent log had only the message, no stack) | `ExecuteRule` catch |
+
+### The setting
+
+`TenantConfiguration.EnableGatherRuleDebugLog` (`bool?`, default null→false), served to the
+agent as `AgentConfigResponse.EnableGatherRuleDebugLog` — **ConfigVersion 36**. Portal:
+Settings → Agent → Settings, toggle "Gather Rule Debug Log", stored via the usual
+tenant-config roundtrip (`TableConfigRepository` Store+Map). Also shown in the admin
+tenant-config report.
+
+`RemoteConfigMerger` projects the bool onto a runtime path (same pattern as
+`EnableImeMatchLog`): `true` → `Constants.GatherRuleDebugLogPath` =
+`%ProgramData%\AutopilotMonitor\Logs\gather_rules_debug.log`; `false` → null, unless a
+`--gather-debug-log <path>` CLI override supplied a non-default path. The field is not
+security-sensitive and deliberately **survives the offline config cache**.
+
+### The trace file
+
+`GatherRuleDebugLog` is an append-only writer held by `GatherRuleExecutor` and exposed
+to collectors via `GatherRuleContext.DebugLog(ruleId, stage, message)` (null-safe no-op
+when disabled — zero cost on the normal path). Line format:
+
+```
+2026-07-28T09:15:02.123Z | RULE-ID | stage | message
+```
+
+Stages: `config` (registration summary per rule, header, zero-rules note), `phase`
+(enrollment-phase transition marker `phase change: Old -> New`, ruleId `-` — every
+rule-level line below it reads against the new phase), `trigger` (timer scheduled,
+phase/event fired, dedup), `scope` (skips with reason incl. current phase), `exec`
+(execution start), `collector` (null/empty results with likely cause), `guard`
+(allowlist block), `emit` (event emitted, hash change), `suppress` (on_change
+suppression with hash prefix + streak), `logparser` (per-file outcome: lines read,
+position range, match count, parse failures, regex timeouts, mode; plus the
+`format=text` hint when every line fails CMTrace parsing; plus one line **per regex
+match** — line number, matched text, capture groups — capped at 10 per file per run),
+`error` (full exception **with stack trace** — the agent log keeps only the message;
+an invalid logparser regex is reported here including the offending pattern string).
+
+Volume control: 10 MB cap with a single `.old` rotation generation (~20 MB worst case).
+Every write failure is swallowed — tracing must never break gathering. The trace never
+leaves the device on its own — but because it lives in the agent log folder
+(`Constants.LogDirectory`), the diagnostics package (`DiagnosticsPackageService`,
+`*.log` pattern, `AgentLogs/` section) picks it up automatically, so a customer-initiated
+diagnostics upload hands the trace to support without manual copying.
+
+### Semantics
+
+* **No hot-reload** — the flag is consumed once when `DefaultComponentFactory` builds
+  the `GatherRuleExecutorHost` at session start (per-enrollment lifecycle, same as
+  `EnableImeMatchLog`). Enable it in the tenant, then the *next* enrollment writes the
+  trace.
+* **Zero-rules case is traced too** — flag on + backend delivered no gather rules →
+  a one-shot standalone `config` line, so the file is never just absent.
+* **`--run-gather-rules` always traces** (operator diagnostic mode; CLI override or
+  default path) and mirrors every line to the console under `--console`.
+
+## Examples
+
+A logparser rule with `emit_mode=on_change` that "delivers nothing" becomes:
+
+```
+... | LP-01 | config | registered: trigger=interval, collector=logparser, target=C:\...\app.log, unscoped, emitMode=on_change, interval=300s
+... | LP-01 | trigger | interval timer scheduled every 300s (first run after one full interval — no immediate execution)
+... | -     | phase | phase change: DeviceSetup -> AccountSetup
+... | LP-01 | exec | executing: collector=logparser, target=C:\...\app.log
+... | LP-01 | logparser | app.log: read 1000 lines from position 0->81234, matched 0, parseFailures=1000, regexTimeouts=0, mode=cmtrace
+... | LP-01 | logparser | every line failed CMTrace parsing — if this is a plain-text log, set parameter format=text
+```
+
+— the answer ("plain-text log parsed in CMTrace mode") is in the file.
+
+A matching rule shows *how* it matched (capped at 10 per-match lines per file per run):
+
+```
+... | LP-02 | logparser | setupact.log: line 42 matched "Error 0x80070005" — groups: code="0x80070005"
+... | LP-02 | logparser | setupact.log: read 500 lines from position 0->40123, matched 1, parseFailures=0, regexTimeouts=0, mode=text
+```
+
+and a broken regex names itself:
+
+```
+... | LP-03 | error | invalid regex pattern '([unclosed' — rule can never match: Invalid pattern '([unclosed' at offset 10. Not enough )'s.
+```
+
+## Citations
+
+* Executor + trace points: `../../src/Agent/AutopilotMonitor.Agent.V2.Core/Monitoring/Telemetry/Gather/GatherRuleExecutor.cs`
+* Writer: `../../src/Agent/AutopilotMonitor.Agent.V2.Core/Monitoring/Telemetry/Gather/GatherRuleDebugLog.cs`
+* Config projection: `../../src/Agent/AutopilotMonitor.Agent.V2.Core/Configuration/RemoteConfigMerger.cs`
+* Backend serve + ConfigVersion: `../../src/Backend/AutopilotMonitor.Functions/Functions/Config/GetAgentConfigFunction.cs`
+* Phase scoping / emit mode background: `../rules/gather-rule-phase-scoping.md`

docs/backend/cloudpc-device-validation.md

@@ -0,0 +1,142 @@
+---
+type: Concept
+title: W365 Cloud PC Device Validation — Cert-CN-Bound Fallback Validator
+description: Why Windows 365 Cloud PCs can never pass the Autopilot serial lookup, and how the CloudPc validator admits exactly the tenant's service-provisioned Cloud PCs by binding the MDM certificate's Subject CN (= Intune device id) to the Graph virtualEndpoint/cloudPCs inventory.
+resource: src/Backend/AutopilotMonitor.Functions/Security/CloudPcDeviceValidator.cs
+tags:
+  - backend
+  - security
+  - device-validation
+  - windows365
+  - cloudpc
+  - graph
+timestamp: 2026-08-06T00:00:00+02:00
+---
+
+# W365 Cloud PC Device Validation
+
+Windows 365 Cloud PCs are provisioned headless by the Windows 365 service and are
+**structurally never Autopilot-registered** — the serial lookup against
+`windowsAutopilotDeviceIdentities` (and the Corporate Identifier fallback, whose
+serials nobody can pre-import for VMs minted at provisioning time) always misses.
+Before this validator, a Cloud PC agent died in the 403 "Device not registered"
+even though its mTLS cert was perfectly valid, so Cloud PC first-connect
+enrollment (Account Setup, RealmJoin, Hello) could not be monitored.
+
+# Schema — the validator chain
+
+`SecurityValidator.ValidateRequestAsync` stage 4 runs the same chain for every
+device; there is **no device-type routing** and the local W365 markers
+(Windows365 registry key, CloudManagedDesktopExtension service) are never
+consulted for auth — they gain an attacker nothing:
+
+1. **Autopilot serial lookup** (`ValidateAutopilotDevice`) — unchanged primary.
+2. **Corporate Identifier** (`ValidateCorporateIdentifier`) — unchanged fallback.
+3. **CloudPc** (`ValidateCloudPcDevice`, default off) — only reached when 1+2
+   missed. Extracts the Intune device id from the **chain-validated** client
+   certificate's Subject CN (`TryGetIntuneDeviceIdFromCertSubject`: CN present
+   AND canonical GUID, else definitive reject) and requires a `cloudPC` object
+   with `managedDeviceId eq <CN>` in the claimed tenant
+   (`GET /v1.0/deviceManagement/virtualEndpoint/cloudPCs?$filter=…`).
+   `ValidatedBy = ValidatorType.CloudPc (5)`.
+
+Only machines actually provisioned by the Windows 365 service have a `cloudPC`
+object — a regular Intune-enrolled non-Autopilot device still ends in the 403,
+so the "Autopilot devices only" contract of stages 1–2 is not widened. The
+tenant hard gate accepts `ValidateCloudPcDevice` as a third satisfying flag.
+
+## Why the cert CN, not headers or local markers
+
+Field-verified 2026-08-06 on a real W365 Enterprise Cloud PC (gktatooine.net):
+
+- MDM client cert Subject `CN=07623d56-…` == Intune `managedDevice.id` ==
+  `cloudPC.managedDeviceId`. The CN cannot be forged without the Intune MDM
+  Device CA (chain pinned to embedded roots, `CustomRootTrust`).
+- `$filter=managedDeviceId eq '…'` is supported server-side on **v1.0** — no
+  paging fallback needed.
+- `managedDevice.serialNumber` matches local `Win32_BIOS.SerialNumber` exactly;
+  the "Cloud PC Enterprise …" model string exists **only** in Graph, never in
+  local WMI (local WMI reports Manufacturer='Microsoft Corporation',
+  Model='Virtual Machine').
+
+Threat model: a valid Intune cert from a *different* tenant fails (its CN does
+not exist in the claimed tenant's Cloud PC inventory — this is a *tenant
+binding* the serial-based validators do not have); spoofed serial headers and
+faked local W365 markers are irrelevant (never consulted); a rogue enrolled VM
+with doctored SMBIOS cannot mint a `cloudPC` object (service-side state, not
+device-reported inventory — the reason the model-string gate was rejected).
+Retired/deprovisioned Cloud PCs disappear from the inventory and their
+validation dies with them (compensates the absent cert revocation check).
+Residual: a compromised *legitimate* Cloud PC of the tenant — same trust level
+as any tenant device today, rate-limited by cert thumbprint.
+
+## Graph permission plumbing
+
+- Optional add-on permission `CloudPC.Read.All` — NOT part of the default
+  consent set. Feature `W365CloudPcValidation` in `GraphFeatureCatalog` →
+  surfaces automatically in the "Optional Graph capabilities" UI (the feature
+  table and grant command are backend-driven) and in
+  `Grant-AutopilotMonitorAddOn.ps1` (`-Features W365CloudPcValidation`).
+  `GraphFeatureCatalogSyncTests` pins C# catalog ↔ grant script (previously
+  comment-only lock-step).
+- A Graph **403** (permission not granted) is a definitive negative (cached
+  5 min), NOT transient — a 503 Retry-After loop cannot fix a missing grant.
+  The error message names the add-on feature.
+- Same resilience contract as `AutopilotDeviceValidator`: 30/5 min
+  positive/negative cache, 2 attempts, transient → agent-facing 503.
+
+## Bootstrap script interplay (v2.3-dev.3)
+
+The Cloud-PC relax in `Install-AutopilotMonitor-dev.ps1` additionally exempts
+**guard 4** (12 h uptime window): a Cloud PC runs headless for days before the
+user's first connect, and the monitorable phase (Account Setup) only starts at
+that first connect — the single-fresh-profile window (< 15 min) is the time
+anchor there, not boot uptime. The OOBE-restore trigger keeps the uptime guard.
+
+## Agent-side IsCloudPc flag + decision-engine expectation
+
+Same change set, agent side. `CloudPcDetector` (V2.Core) re-uses the bootstrap's
+field-verified marker AND — `HKLM\SOFTWARE\Microsoft\Windows365` key **plus**
+installed `CloudManagedDesktopExtension` service (probed via its
+`HKLM\SYSTEM\CurrentControlSet\Services` key; the agent deliberately has no
+`System.ServiceProcess` dependency). SKIP-safe: any error resolves `false`.
+
+Three independent transport rails, never an auth input:
+
+- **Session metadata** — `SessionRegistration.IsCloudPc` →
+  Sessions table (sticky-true OR across re-registrations, like
+  `IsSelfDeployingProfile`) → SessionsIndex full mirror → `SessionSummary` →
+  search filter `isCloudPc` (portal, `/api/search/sessions`, `/api/raw/sessions`,
+  MCP `search_sessions`/`query_raw_sessions`). Agent-reported and unverified —
+  can legitimately disagree with the server-derived `ValidatedBy = CloudPc`
+  (e.g. Cloud PC admitted via a stage that ran earlier).
+- **Distress channel** — `DistressReport.IsCloudPc` (captured once at
+  `DistressReporter` construction, `BackendClientFactory`) rides every pre-auth
+  distress report → `DistressReportEntry.IsCloudPc` → the "Devices Not
+  Registered" report aggregates it **sticky-true** per serial
+  (`GetDeviceNotRegisteredFunction`) and the portal insight renders a Cloud PC
+  badge plus a hint pointing at the Cloud PC validation toggle + the
+  `W365CloudPcValidation` add-on. Same UNVERIFIED contract as all distress
+  fields; rows from older agents read false. Fits the existing 1536-byte
+  payload cap without a bump.
+- **Decision engine** — the marker rides the `EnrollmentFactsObserved` payload
+  (`isCloudPc`), is recorded set-once for BOTH values in
+  `EnrollmentScenarioObservations.CloudPc`, and annotates the scenario profile
+  reason `cloud_pc_first_connect:no_device_esp_expected`. That is the
+  engine-recorded expectation "no Device ESP phase will appear": Device-ESP ran
+  headless at provisioning, the session starts at Account Setup. Deliberately
+  reason+observation only — no completion arm depends on DeviceSetup, `Mode`
+  is still classified by AccountSetup/IME signals (Classic), and `EspConfig`
+  keeps the *configured* FirstSync semantics. The positive marker surfaces as
+  `cloud_pc_marker` in the terminal audit-trail signal census.
+
+# Citations
+
+- `src/Backend/AutopilotMonitor.Functions/Security/CloudPcDeviceValidator.cs`
+- `src/Backend/AutopilotMonitor.Functions/Security/SecurityValidator.cs` — stage 4 chain, `TryGetIntuneDeviceIdFromCertSubject`
+- `src/Shared/AutopilotMonitor.Shared/Models/Graph/GraphFeatureCatalog.cs` — `W365CloudPcValidation`
+- `scripts/CustomerSetup/Grant-AutopilotMonitorAddOn.ps1` — customer-side grant
+- `scripts/Bootstrap/Install-AutopilotMonitor-dev.ps1` — Cloud-PC relax + guard-4 exemption
+- `src/Backend/AutopilotMonitor.Functions.Tests/CloudPcDeviceValidatorTests.cs`, `SecurityValidatorTests.cs`, `GraphFeatureCatalogSyncTests.cs`
+- `src/Agent/AutopilotMonitor.Agent.V2.Core/Security/CloudPcDetector.cs` — agent-side marker AND
+- `src/Shared/AutopilotMonitor.DecisionCore/State/EnrollmentScenarioObservations.cs` — `CloudPc` fact; reason annotation in `EnrollmentScenarioProfileUpdater`

docs/backend/oobe-bootstrap-go-flow.md

@@ -0,0 +1,107 @@
+---
+type: Concept
+title: OOBE Bootstrap go-Code Flow — Always-200 Script Endpoint
+description: The full lifecycle of the bootstrap short-code — created in the portal, typed as `irm go.autopilotmonitor.com/CODE | iex` at Shift+F10, served by GetBootstrapScriptFunction as an always-HTTP-200 PowerShell script — including the two-line injection defense and the rate-limit story behind Front Door.
+resource: src/Backend/AutopilotMonitor.Functions/Functions/Bootstrap/GetBootstrapScriptFunction.cs
+tags:
+  - backend
+  - bootstrap
+  - security
+  - oobe
+timestamp: 2026-07-28T00:00:00+02:00
+---
+
+# OOBE Bootstrap go-Code Flow
+
+Bootstrap Sessions let a technician install the agent **before** Intune
+enrollment: an admin creates a short-lived session in the portal (Settings →
+Bootstrap Sessions), hands the technician a short URL, and the technician types
+`irm https://go.autopilotmonitor.com/CODE | iex` into a Shift+F10 console
+during OOBE. The URL is deliberately short because it is typed by hand on a
+device that has no clipboard.
+
+# Lifecycle
+
+1. **Create** — `POST /api/bootstrap/sessions` (`BootstrapManagerOrGA`).
+   `BootstrapSessionService.CreateAsync` mints an unambiguous-charset short
+   code + a GUID token, validity clamped 1–168 h. The response's `bootstrapUrl`
+   is built from `Constants.BootstrapGoBaseUrl` — the single producer of the
+   absolute URL (pinned by `CreateBootstrapSessionUrlShapeTests`).
+2. **Serve** — `GET /api/bootstrap/go/{code}` (`GetBootstrapScriptFunction`,
+   `PublicAnonymous`). Customers reach it through the Front Door custom domain
+   `go.autopilotmonitor.com`, whose `/*` route rewrites onto the API path.
+   Validation runs in-process (`ValidateCodeAsync` + the tenant's
+   `BootstrapTokenEnabled` gate) — no HTTP hop to the validate endpoint.
+3. **Install** — the generated script downloads the agent ZIP from
+   `Constants.AgentDownloadBaseUrl`, extracts, and runs
+   `--install --no-auth --bootstrap-token … --tenant-id …`. The agent monitors
+   from OOBE start, switches to certificate auth after Intune enrollment, and
+   self-destructs on completion.
+
+The legacy Next.js `/go/[code]` route (SSR on the SWA) stays alive only for
+URLs issued before the migration and is removed with the static-export PR —
+see the transition rule in [URL Registry](../url-registry.md).
+
+# Always-200 contract
+
+Every response — success, invalid format, unknown/expired code, disabled
+feature, rate limit, internal error — is **HTTP 200 `text/plain`**. The
+consumer is `irm | iex`: a non-2xx status would make `irm` throw an opaque
+exception on the OOBE console, while a 200 error script surfaces the actual
+message via `Write-Host 'ERROR: …'`. Consequences:
+
+- Failures are invisible in status-code metrics; the compensating signal is the
+  `LogWarning` per rejection (code + client IP).
+- Error messages are capped at 200 chars **before** quote-escaping and
+  single-quote-doubled — a hostile upstream message cannot break out of the
+  `Write-Host` literal.
+
+A disabled tenant returns the **same generic message** as an unknown code — no
+enumeration oracle for whether a code exists.
+
+# Injection defense (two lines)
+
+The script runs as SYSTEM during OOBE, so interpolation is treated as a
+security boundary:
+
+1. **`BootstrapScriptValueValidator`** — tenantId/token must be exact canonical
+   GUIDs, the download URL must be https on an allow-listed host
+   (`AgentDownloadBaseUrl`/`AgentBlobBaseUrl` hosts) with the strict
+   `/agent/….zip` path shape, expiry must be future and ≤ 14 days. No accepted
+   value can contain `$`, quotes, backticks, spaces, or newlines. Kept even
+   though values are produced in-process — defense-in-depth against tampered
+   table data.
+2. **Single-quoted PS literals** — every interpolated value sits inside
+   single-quoted PowerShell strings, which do not expand `$()`, `$var`, or
+   backticks.
+
+The template is a C# raw string with `__TOKEN__` placeholders substituted via
+`Replace` (never `$`-interpolation — the script is full of PS `$vars`).
+`OobeBootstrapScriptGeneratorTests` pins byte parity with the original
+TypeScript template through a golden file, so the legacy route and the backend
+serve identical scripts during the transition.
+
+# Rate limiting behind Front Door
+
+The endpoint self-limits per client IP (`bootstrap-script:{ip}`, 20/min via
+`ClientIpExtractor.GetRateLimitClientIp`) — anonymous routes are skipped by
+`UserRateLimitMiddleware` and must bring their own limiter. Because traffic
+arrives through Front Door, the rightmost X-Forwarded-For hop resolves to AFD
+egress IPs and buckets would collapse (the shared-bucket 429 incident class);
+the AFD-aware extraction therefore honors `X-Azure-ClientIP` only when
+`X-Azure-FDID` matches the `FrontDoorProfileId` app setting (fail-closed to
+the trusted-hop path otherwise). Verified post-deploy 2026-07-29: real client
+IPs are keyed, not AFD egress.
+
+Front Door route caching is DISABLED for this route: the body inlines the
+bearer token, so a cache hit would replay one requester's token to another.
+`NoStoreCacheMiddleware` covers the `/api/bootstrap/go/` prefix.
+
+# Citations
+
+- `src/Backend/AutopilotMonitor.Functions/Functions/Bootstrap/GetBootstrapScriptFunction.cs`
+- `src/Backend/AutopilotMonitor.Functions/Functions/Bootstrap/OobeBootstrapScriptGenerator.cs`
+- `src/Backend/AutopilotMonitor.Functions/Security/BootstrapScriptValueValidator.cs`
+- `src/Backend/AutopilotMonitor.Functions.Tests/OobeBootstrapScriptGeneratorTests.cs` — golden parity
+- `src/Web/autopilot-monitor-web/app/go/[code]/route.ts` — legacy route (transition only)
+- [URL Registry](../url-registry.md) — go-URL registry entries + transition rule

docs/backend/tenant-activation-welcome-mail.md

@@ -0,0 +1,75 @@
+---
+type: concept
+title: Tenant Activation & the Once-Only Welcome Mail
+description: How a signup becomes an activated tenant (manual approve or auto-approve queue), and how the welcome mail is sent exactly once even though activation and the user-provided address race each other.
+resource: backend
+tags: [activation, auto-approve, welcome-email, preview-whitelist, race]
+timestamp: 2026-08-02
+---
+
+# Schema
+
+## Activation
+
+A tenant is **activated** when the row `PartitionKey={tenantId}, RowKey="approved"` exists
+in the `PreviewWhitelist` table (legacy name kept on purpose). Everything else in the
+portal gates on that row via `PreviewWhitelistService.IsApprovedAsync` (5 min positive /
+30 s negative cache).
+
+Two activation routes, one shared implementation
+(`TenantApprovalService.ApproveWithSideEffectsAsync`):
+
+* **Manual**: Global Admin approves in the admin panel (`POST /api/preview/whitelist/{tenantId}`).
+* **Auto**: signup unconditionally enqueues a `tenant-auto-approve` envelope; the queue
+  worker (`TenantAutoApproveHandler`) re-checks the `AutoApproveNewTenants` flag
+  (uncached, fail-closed), the suspension gate (fresh config read), then approves.
+  Typical latency: ~1 minute after signup.
+
+The whitelist add is a **conditional INSERT** (`AddEntityAsync`, 409 = lost) — storage
+arbitrates concurrent activations; exactly one caller runs the side effects
+(TenantAdmin auto-promote of the signup UPN, welcome mail, `TenantAutoApproved` ops event).
+
+## The welcome-mail race
+
+The welcome mail goes to the **notification email** (`RowKey="notification-email"` in the
+same table) — the only reliable address: it is typed by the user on the activation-pending
+page (`PUT /api/preview/notification-email`). The signup admin UPN may have no mailbox and
+`ContactEmail` is merely seeded from the notification email.
+
+That makes activation and address entry concurrent writers. With auto-approve, activation
+usually wins (observed in production: approve at T+64 s, address saved at T+69 s → the
+approval path found no address and the mail was silently skipped).
+
+**Arbitration — write-then-read on both sides plus a send-once marker:**
+
+* The approval path writes the `approved` row, then reads the address.
+* The save path (`SavePreviewNotificationEmail`) writes the address row, then checks
+  approval **fresh** (`IsApprovedFreshAsync` — the 30 s negative cache would hide the
+  activation for exactly this window).
+* Since both do write-then-read, at least one sees both halves and calls
+  `TenantApprovalService.TrySendWelcomeEmailAsync`.
+* There, a conditional insert of `RowKey="welcome-email-sent"` decides who actually
+  sends: at most one wins. The marker is consumed strictly **after** the address check —
+  consuming it without an address would permanently suppress the mail.
+
+Marker lifecycle: revoke (`RevokeAsync`) deletes it (re-approve = fresh activation =
+fresh mail); the offboarding cascade wipes the whole `PreviewWhitelist` partition anyway.
+The Global-Admin resend endpoint (`POST /api/preview/send-welcome-email/{tenantId}`)
+always sends (explicit intent) and consumes the marker best-effort so the automatic
+paths never duplicate afterwards.
+
+# Examples
+
+* Auto-approve wins the race: approve at T+64 s finds no address → logs "deferred to the
+  notification-email save path"; user saves address at T+69 s → save path sees approved
+  (fresh read), wins the marker, sends. Response carries `welcomeEmailSent: true`.
+* Address saved before manual approve (classic shape): approval path finds the address,
+  wins the marker, sends; a later re-save of the same address does not re-send.
+
+# Citations
+
+* `src/Backend/AutopilotMonitor.Functions/Services/TenantApprovalService.cs` — shared activation + `TrySendWelcomeEmailAsync`
+* `src/Backend/AutopilotMonitor.Functions/Services/Activation/TenantAutoApproveHandler.cs` — queue-side gates
+* `src/Backend/AutopilotMonitor.Functions/Functions/Rules/PreviewWhitelistFunction.cs` — save-path trigger, GA resend
+* `src/Backend/AutopilotMonitor.Functions/DataAccess/TableStorage/TableConfigRepository.cs` — conditional inserts (approved / welcome-email-sent)
+* `src/Backend/AutopilotMonitor.Functions.Tests/TenantApprovalServiceTests.cs` — ordering + dedup pins

docs/index.md

@@ -20,6 +20,7 @@ https://docs.autopilotmonitor.com (separate repository).
 * [V2 Agent](agent/index.md) - How the on-device agent works: [runtime overview](agent/overview.md), [decision engine](agent/decision-engine.md) (reducer, signals, completion arms), [logs & persistence](agent/logs-and-persistence.md) (signal log, snapshot, crash recovery), [Hello wizard un-skip](agent/hello-wizard-unskip.md) (why a single "WHfB disabled" read never decides completion), [Autopilot ZTD diagnostics](agent/autopilot-ztd-diagnostics.md) (event IDs, diagnostic registry, endpoints, error-code map).
 * [Build Counter Blob](agent/build-counter-blob.md) - How agent build numbers are minted: shared counter blob with ETag-CAS so local and CI builds never collide; CI additionally attests build provenance (Sigstore).
 * [Agent Endpoint Migration](agent/endpoint-migration.md) - How the backend re-homes agents to a new API base URL via the config channel (backend move or per-tenant region move): live-fetch-only, allowlist-validated on both sides, one hop, kill wins.
+* [Gather Rule Debug Log](agent/gather-rule-debug-log.md) - EnableGatherRuleDebugLog (ConfigVersion 36): the per-tenant local trace file that explains every gather-rule evaluation decision — scope skips, on_change suppression, empty collector results, logparser position/parse-mode outcomes — for rules that produce no timeline events.
 * [MDM Reboot Coalescing](agent/mdm-reboot-coalescing.md) - Attributing the mid-ESP coalesced reboot ("second sign-in") to the device-assigned policy URIs that forced it: aggregated DM-Enterprise 2800 observations (neutral, flush-time watermark) + the ANALYZE-ESP-005 advisory gated on an actually-observed reboot.
 * [Secure Boot CA-2023 Detection](agent/secureboot-ca2023-detection.md) - Why ANALYZE-SEC-001 v3 reads the UEFI db/KEK variables directly instead of trusting the SecureBoot\Servicing registry, and how the one-sided uefiCa2023FirmwareConfirmed marker plus a not_exists precondition give absence-tolerant suppression across old and new agents.
 * [ESP Policy-Provider Stall Detection](agent/esp-policy-provider-stall.md) - The EnrollmentStatusTracking CSP's no-timeout Setup/Apps wait is keyed to the Intune-registered "Sidecar" provider by NAME: co-management's "ConfigMgr" parks the user ESP at "Apps (Identifying)" for days even with TrackingPoliciesCreated=1 (issue #106); the always-on two-arm esp_policy_provider_stalled tripwire (provider_incomplete | sidecar_provider_missing) and the SOFTWARE\Microsoft\Windows\Autopilot gather-rule allowlist entry that surface it.
@@ -28,22 +29,27 @@ https://docs.autopilotmonitor.com (separate repository).
 
 * [Gather Rule Phase Scoping, One-Shot Triggers & Emit-on-Change](rules/gather-rule-phase-scoping.md) - Restricting gather rules to enrollment phases (activePhases / activeFromPhase sticky latch), one-shot collection at a phase's start/end (phase_change / phase_exit), and emitMode "on_change" result-dedup.
 * [Gather Rule Guardrails](rules/gather-rule-guardrails.md) - Why the allowlists in rules/guardrails.json are enforced on the agent and nowhere else, which hard blocks survive unrestricted mode, and the rule that every collector must call a guard and emit security_warning on refusal.
+* [Rule Authoring Surface](rules/rule-authoring-surface.md) - How customer AIs author rules against the real contract: the baked MCP resources (guide/schemas/guardrails via combine.js), the MCP-local validate_rule pre-flight, and the side-effect-free POST rules/analyze/dryrun whose trace twin shares the production evaluators (parity + side-effect-freedom pinned by tests).
 
 # Backend
 
 * [Business Timestamps](backend/business-timestamps.md) - Why the Azure Tables system Timestamp is never authoritative (migrations reset it), and the OccurredUtc + RowKey-decode compensation for AuditLogs/OpsEvents/Events after the 2026-07-18 migration.
+* [OOBE Bootstrap go-Code Flow](backend/oobe-bootstrap-go-flow.md) - The bootstrap short-code lifecycle (portal-created session → `irm go.autopilotmonitor.com/CODE | iex` at Shift+F10 → GetBootstrapScriptFunction), the always-HTTP-200 text/plain contract, the two-line injection defense (GUID/URL/expiry validator + single-quoted PS literals, golden-pinned against the legacy TS template), and the per-IP rate-limit story behind Front Door.
 * [Device Journeys & First-Time-Right](backend/device-journeys.md) - How a device's terminal enrollment attempts are grouped into journeys (trim+casefold device key with junk-serial exclusion, first-success end, 30-day gap, WhiteGlove = one attempt), the DeviceHistories chain with its tombstone-driven deleted-session pruning, the additive daily FTR aggregates, and the banner/fleet/MCP surfaces.
 * [Enrollment Time Attribution](backend/time-attribution.md) - How a terminal session's authoritative wall clock (DurationSeconds, WhiteGlove pause excluded) is partitioned into named segments with an explicit unattributed remainder, ESP-blocking apps as positive evidence with "up to" what-if bounds, reboot spans from event gaps, and the breakdown/aggregate tables the sweep maintains.
 * [Rule Regression Radar](backend/rule-regression-radar.md) - How analyze-rule hit-rate regressions are detected (7-day window ≥2× the 28-day baseline with disjoint Wilson intervals), which suppressions keep the radar quiet (grace period, edit-in-window, kill switch), how alert episodes live in the ruleregression tracker keyspace with re-arm semantics, and the on-fire dimension correlation with its "correlated, not necessarily causal" wording contract.
+* [Tenant Activation & the Once-Only Welcome Mail](backend/tenant-activation-welcome-mail.md) - How a signup becomes an activated tenant (manual approve or the auto-approve queue), and the write-then-read + conditional-marker arbitration that sends the welcome mail exactly once even though activation and the user-typed notification address race each other.
+* [W365 Cloud PC Device Validation](backend/cloudpc-device-validation.md) - Why Cloud PCs can never pass the Autopilot serial lookup, and the cert-CN-bound CloudPc fallback validator: Subject CN (= Intune device id) matched against the tenant's Graph virtualEndpoint/cloudPCs inventory — admits exactly the service-provisioned Cloud PCs, nothing else.
 * [ServerActions & On-Demand Diagnostics](backend/server-actions-on-demand-diagnostics.md) - The queue-on-session, deliver-on-ingest action channel, the TenantAdminOrOperator tier with in-function per-type re-gating, the portal's Collect Logs flow (quick-config orders rotate_config before request_diagnostics), and the hosted-prefix sweep in the offboarding cascade.
 
 # MCP Server
 
 * [MCP Docs Corpus](mcp/docs-corpus.md) - How the published customer documentation becomes the `search_docs` corpus: CRLF-safe heading chunking, build-time embedding as a third precomputed section, and why a docs edit needs an MCP redeploy.
+* [MCP Tool Telemetry](mcp/tool-telemetry.md) - The three telemetry layers for judging tool quality: backend App Insights via X-MCP-Tool-Name, the per-user usage table, and the MCP_TOOL_LOGGING stderr lines (soft errors, result size vs. cap, zero-hit searches, Zod rejections).
 
 # Web Portal
 
-* [Portal Navigation Prefetch & the SWA Runtime Bottleneck](web/portal-navigation-prefetch.md) - Why every navigation Link sets `prefetch={false}`: the App Router's viewport prefetch fans out one RSC request per visible link against an HTTP/1.1 Static Web Apps runtime, and its latency tail starves the six connections that also serve the document and the route chunks. Includes where browser telemetry actually lives.
+* [Portal Navigation Prefetch & the SWA Runtime Bottleneck](web/portal-navigation-prefetch.md) - Why every navigation Link sets `prefetch={false}`: the App Router's viewport prefetch fans out one RSC request per visible link and the Static Web Apps SSR runtime queues them server-side into a multi-minute tail. Records the follow-up measurement (the Standard plan changed nothing; the prefetch storm was an accidental keep-alive), where browser telemetry actually lives, and why this curl build cannot be trusted for HTTP versions.
 
 # Security & Identity
 

docs/log.md

@@ -1,8 +1,51 @@
 # Log
 
+## 2026-08-07 (later)
+
+* **Update**: `backend/cloudpc-device-validation.md` — third `IsCloudPc` transport rail: the pre-auth distress channel. `DistressReport.IsCloudPc` (CloudPcDetector verdict captured at `DistressReporter` construction) → `DistressReportEntry`/table column → "Devices Not Registered" aggregation (sticky-true per serial, same OR semantics as the Sessions merge) → portal Cloud PC badge + actionable hint ("enable Windows 365 Cloud PC Validation + W365CloudPcValidation add-on"). Motivated by the first W365 field run: the rejected Cloud PC showed up as anonymous "Microsoft Corporation / Virtual Machine" with no clue that the fix is the Cloud PC validator, not Autopilot registration. UNVERIFIED like all distress fields; ≤18 bytes, fits the 1536-byte cap.
+
+## 2026-08-07
+
+* **Update**: `backend/cloudpc-device-validation.md` — the "deliberately out of scope" follow-up landed in the same PR: agent-side `IsCloudPc` flag (`CloudPcDetector`, bootstrap-verified marker AND: Windows365 key + CloudManagedDesktopExtension service key, SKIP-safe) rides two rails — `SessionRegistration` → Sessions/Index (sticky-true) → `SessionSummary` + `isCloudPc` search filter (portal/raw/MCP), and the `EnrollmentFactsObserved` payload → `EnrollmentScenarioObservations.CloudPc` (set-once, both values) with profile reason `cloud_pc_first_connect:no_device_esp_expected` + `cloud_pc_marker` in the audit-trail census. Reason+observation only: no completion arm depends on DeviceSetup, Mode stays AccountSetup/IME-classified, EspConfig keeps configured-FirstSync semantics. Never an auth input.
+
+## 2026-08-06
+
+* **Creation**: Added `backend/cloudpc-device-validation.md` — the CloudPc fallback validator (`ValidatorType.CloudPc = 5`, tenant flag `ValidateCloudPcDevice`): W365 Cloud PCs are structurally never Autopilot-registered, so stage 4 gains a third stage that binds the chain-validated MDM cert's Subject CN (= Intune device id, field-verified on a real Cloud PC) to the tenant's `virtualEndpoint/cloudPCs` inventory — admits exactly the service-provisioned Cloud PCs, no device-type routing, local W365 markers never consulted for auth. New optional Graph add-on `W365CloudPcValidation` → `CloudPC.Read.All` (catalog + grant script now pinned by `GraphFeatureCatalogSyncTests`; Graph 403 = definitive "grant missing", not transient). Bootstrap dev script v2.3-dev.3 exempts guard 4 (uptime) while the Cloud-PC relax is active — the fresh-profile window is the time anchor at first connect, not boot uptime. Follow-up deliberately out of scope: agent-side `IsCloudPc` classification + decision-engine "no Device ESP" expectation.
+
+## 2026-08-05 (later)
+
+* **Update**: `rules/rule-authoring-surface.md` — new section `POST /api/rules/gather/test-pattern`: the logparser pattern tester (agent-exact .NET matching: no IgnoreCase, first-match-per-line, cmtrace vs text mode, verbatim format=text hint), motivated by a field incident where a PHP-verified regex behaved differently under .NET. `CmTraceLogParser` moved Agent → `AutopilotMonitor.Shared.Logging` so agent and backend share the ONE parsing implementation (timestamp caveat: AssumeLocal = server TZ on backend, endpoint reports no timestamps). MCP: new `test_log_pattern` tool, logparser lint in `validate_rule`, guide gains the case-sensitivity/engine-mismatch pitfalls.
+
+## 2026-08-05
+
+* **Creation**: Added `mcp/tool-telemetry.md` — the three MCP tool-telemetry layers (App Insights `McpToolName`, per-user usage table, `MCP_TOOL_LOGGING` stderr lines) and the new quality signals: soft-error capture (`toolError` returns instead of throwing, so backend telemetry counted those calls as successes), `resultChars`/`overCap` vs. the inline-size hint, bounded args summaries, caller scope, `search_zero_hit` on the three search tools (unmet-demand signal), and `tool_call_rejected` for JSON-RPC-level Zod/unknown-tool rejections sniffed at the `/mcp` route (previously invisible everywhere). Bicep default for `toolLoggingEnabled` flipped to `true` (documented desired state; live flag set via `az containerapp update`).
+* **Creation**: Added `rules/rule-authoring-surface.md` — the AI-assisted rule-authoring stack: three deterministic MCP resources (`rule_authoring_guide` hand-written, `rule_schemas` + `rule_guardrails` generated into `rule-authoring.generated.ts` by a new combine.js emitter, drift-guarded twice), the MCP-local `validate_rule` (ajv 2020-12 against the single-rule $defs, guardrail pre-flight mirroring GatherRuleGuards matching semantics incl. hard blocks, semantic lint for schema-valid-but-dead rules), and the side-effect-free `POST /api/rules/analyze/dryrun` (TenantAdminOrGlobalReader; `RuleEngine.DryRun.cs` trace twin sharing the production evaluators, all-conditions trace with per-condition evidence + matchingEventCount, parity and side-effect-freedom pinned by RuleEngineDryRunTests). MCP `test_analyze_rule` wraps the endpoint with `{{token}}`-interpolated previews; `author-rule` prompt drives the draft → validate → dry-run loop. Deliberately absent: gather-rule remote execution, rule writes via MCP.
+
+## 2026-08-04
+
+* **Update**: `rules/gather-rule-phase-scoping.md` — new section "Which phase feeds the triggers": `GatherRuleExecutorHost` now drives `phase_change`/`phase_exit`/`on_event` gather triggers (and the phase-scope gates) from the post-reduce `TimelineEventStream` (every emitted event's `(eventType, phase)` published by `EventTimelineEmitter`) instead of the pre-reduce `SignalIngress.SignalPosted` payloads. Trigger: session `32312a32` (RealmJoin tenant rsneuffen.de) — a Phase-Start rule on FinalizingSetup fired at the raw ESP-exit `EspPhaseChanged(FinalizingSetup)` signal, 7 minutes before the engine's RealmJoin-gated `phase_transition(FinalizingSetup)`, reading `HKLM\SOFTWARE\RealmJoin\Custom\BIOS` before the RealmJoin package created it. Phase triggers now fire exactly when the timeline shows the phase; `on_event` additionally sees engine-emitted event types (`enrollment_complete`, `realmjoin_resolved`, …) for the first time in V2, restoring V1 semantics and the documented end-of-enrollment pattern. Other raw-signal hosts (DeviceInfo, keep-awake, PPKG) deliberately unchanged.
+
+## 2026-08-02
+
+* **Creation**: Added `backend/tenant-activation-welcome-mail.md` — triggered by the first production auto-approve (activation at signup+64 s, notification address saved at +69 s → welcome mail silently skipped, since the approval path is the only sender and reads the address once). Fix documented in the doc: the notification-email save path now also triggers the send (`PUT /api/preview/notification-email` → fresh approval check `IsApprovedFreshAsync`, bypassing the 30 s negative cache), and a conditional-insert `welcome-email-sent` marker in `PreviewWhitelist` makes the send once-only across both racing paths (marker consumed strictly after the address check; revoke clears it, offboarding wipes the partition, the GA resend endpoint sends unconditionally and consumes it best-effort).
+
+## 2026-07-29
+
+* **Update**: `agent/gather-rule-debug-log.md` — three trace enrichments: (1) new `phase` stage writing an enrollment-phase transition marker (`phase change: Old -> New`, ruleId `-`) so every rule-level line reads against the current phase; (2) logparser now writes one line per regex match — line number, matched text, capture groups — capped at 10 per file per run (the per-file summary keeps the full count); (3) the invalid-regex `error` line includes the offending pattern string.
+
+* **Update**: `url-registry.md` (+ `web/portal-navigation-prefetch.md` context) — the portal is now a **full static export** (`output: 'export'`, `trailingSlash: true`): the SWA serves plain files, the managed SSR runtime — the portal's last cold-start source ("Backend call failure" > 45 s) — no longer exists. Detail routes moved from path params to query strings (`/sessions?id=`, `/sessions/inspector?id=`, `/diagnosis?id=`, `/apps/detail?name=`, `/admin/backups/detail?id=`, `/admin/customs-archive/detail?tenantId=&rowKey=`) with all 21 link sites going through the new single-definition builders in `lib/routes.ts`; the 9 `[section]` families prerender via `generateStaticParams` server shells (37 pages, `dynamicParams=false`), server `redirect()` index pages became `ClientRedirect` shells. Legacy PATH-shaped deep links (sent Teams/Slack/webhook notifications hold `/sessions/{id}` forever) are preserved permanently: SWA wildcard rewrites serve the family page and the globally mounted `LegacyPathRedirect` rewrites to the canonical query URL (hash + query preserved; mapping pinned by `lib/__tests__/legacyPathRedirect.test.ts`). `middleware.ts` host routing became the client-side `HostRoutingGuard` (prefix list moved to `lib/hostRouting.ts`); the legacy `/go/[code]` route + `bootstrapValidation.ts` are deleted (BootstrapSessions table verified free of pre-cutover active sessions). `staticwebapp.config.json` now carries the 19 docs/marketing redirects (order-sensitive), the legacy rewrites, `404.html` override and ALL security headers incl. the literalized prod CSP — guarded by the new `swaConfig.guard.test.ts`; maintenance mode changed from whole-file swap to a first-routes-entry insert (README rewritten). Backend notification deep links go through the new `Constants.PortalSessionUrl` (query shape, pinned). Deploy: `deploy-web.yml` uploads `out/` with `is_static_export: true`.
+
+* **Creation**: Added `backend/oobe-bootstrap-go-flow.md` (and a `Bootstrap go-URL` section + web-registry update in `url-registry.md`) — the OOBE bootstrap script endpoint moved from the portal's Next.js `/go/[code]` SSR route into the Function App (`GET /api/bootstrap/go/{code}`, `GetBootstrapScriptFunction`), unblocking the portal's static export; the customer URL became **`go.autopilotmonitor.com/{code}`** (Front Door custom domain, `/*` route with origin-path rewrite, caching disabled — the script inlines the bearer token). New `Constants.BootstrapGoBaseUrl` (single producer via `CreateBootstrapSessionFunction`) + web `BOOTSTRAP_GO_URL` (display only); both guard host lists extended. Security invariants ported to C#: `BootstrapScriptValueValidator` (exact-GUID tenantId/token, https + host-allowlist + `/agent/….zip` path, expiry ≤ 14 d) and `OobeBootstrapScriptGenerator` (Replace-token raw-string template, single-quoted PS literals, 200-char error cap before quote-doubling; always-HTTP-200 text/plain contract for `irm | iex`). Endpoint is `PublicAnonymous` in the catalog, `NoStoreCacheMiddleware`-covered, self-rate-limited `bootstrap-script:{ip}` 20/min (rate-limit reply is also a 200 error script). Tests: golden byte-parity against the TS template, validator invariants incl. hostile-URL cases, format-gate table, and the previously missing BootstrapUrl shape pin. Transition: the legacy www route + `middleware.ts` `/go` prefix stay alive for pre-migration URLs (validity ≤ 168 h) and are removed in the static-export PR no earlier than 168 h after the last www URL was issued. Customer docs `network-endpoints.md` gained the `go.` host (device-facing, Bootstrap-Sessions-only).
+
+* **Update**: `agent/autopilot-ztd-diagnostics.md` — presentation layer for the startup error backfill (customer feedback: an unannounced wall of pre-agent Error events with a single identical timestamp read like a live failure). Agent: the backfill scan now buffers the capped record set, emits an Info summary event first (`modern_deployment_log`, `backfillSummary: true` + `replayedCount`/`droppedOverCap`/`lookbackMinutes`), then replays oldest-first so the timeline sequence follows event-log chronology. Web: `EventTimeline.tsx` badges `backfilled: true` events („⟲ Backfilled", tooltip) and renders the original `timeCreated` as the row time with a "(reported …)" suffix plus a `Recorded` metadata line — works retroactively for already-stored events. Severity is deliberately not downgraded.
+
+* **Creation**: Added `agent/gather-rule-debug-log.md` — the new per-tenant setting `EnableGatherRuleDebugLog` (ConfigVersion 35 → 36, portal toggle under Settings → Agent, `EnableImeMatchLog`-style bool→path projection in `RemoteConfigMerger`). When enabled, the agent writes `%ProgramData%\AutopilotMonitor\Logs\gather_rules_debug.log`: one pipe-delimited line per evaluation decision across ten previously silent "produced nothing" exits — disabled rules, `interval` without `intervalSeconds` (never runs), the first-tick-after-one-full-interval window, phase-scope skips incl. `currentPhase=Unknown`, per-(rule, phase) dedup, empty collector results (`emitOnlyIfExists`), `on_change` hash suppression (hash prefix + streak), guard blocks, logparser per-file outcomes (position skips, parse failures with a `format=text` hint when every line fails CMTrace parsing, `maxLines`/wildcard caps), and full exception stacks that the agent log drops. 10 MB cap + one `.old` generation; no hot-reload (per-enrollment lifecycle); flag survives the offline config cache; `--run-gather-rules` always traces and echoes under `--console`; zero-rules delivery leaves a one-line file instead of nothing. Side fix: `GatherRuleExecutorHost` now passes the logger into `InformationalEventPost`, so gather-event emissions appear in the agent DEBUG log.
+
+* **Correction + Update**: `web/portal-navigation-prefetch.md`. The HTTP/1.1 claim in the 2026-07-27 entry below is **wrong** and has been struck from the document: `portal.autopilotmonitor.com` negotiates **h2**, verified by `openssl s_client -alpn h2,http/1.1` and a .NET `HttpClient` returning `HTTP/2.0`. The false reading came from the Windows/Schannel curl build in this environment, which has no HTTP/2 support and therefore always reports `1.1` — do not use it to determine HTTP versions. There is no six-connection cap in play; the queue is server-side in the SWA SSR runtime, which does not change the fix or the evidence, only the mechanism. Added an `Outcome` section with 20 h of post-change telemetry: the Free → Standard plan change (16:02:44 UTC) produced **no measurable latency gain** once stratified by the gap to the previous request (p50 Free → Standard: `<10s` 85 → 95 ms, `5-30min` 429 → 441 ms; tail rates 1.64 %/0.374 % over 2 s/10 s vs 6 and 1 events at n = 258 against 4.2 and 1.0 expected; `browserTimings` Mann-Whitney z = −0.24, p = 0.81). The freezes were removed by `prefetch={false}` (16:34:13 UTC): worst `browserTimings.totalDuration` 225,277 → 4,856 ms. The prefetch storm was also an **accidental keep-alive** — requests under 10 s apart fell from 85 % to 46 %, and on the identical never-cacheable `/sessions/{id}` route the median rose 87 → 211 ms and p90 465 → 1,480 ms, with one 11,441 ms abandoned request (`resultCode 0`) after 517 minutes idle. Synthetic bursts warm the runtime and must not be used to benchmark this (round 1 p50 288 ms vs rounds 4–25 p50 113 ms).
+
 ## 2026-07-27
 
-* **Creation**: Added `web/portal-navigation-prefetch.md` (and a `Web Portal` section to the index) — root cause of the minute-long portal freezes. `GlobalSidebar` and `Navbar` render the whole navigation on every page, so the App Router's default viewport prefetch issued one `?_rsc=` request per visible link against `portal.autopilotmonitor.com` (~10,400 in 14 days). That origin serves the document, the route chunks and the RSC payloads over **HTTP/1.1**, so the six-connection-per-origin cap applies; when the Static Web Apps managed runtime queued the prefetches (p50 91 ms, p95 896 ms, but max 234 s / 21 samples over 30 s), the in-flight prefetches held every socket and the navigation the user wanted could not get one. Measured on the 2026-07-27 17:25 CEST incident: `/admin/presence?_rsc=` 151 s, three siblings finishing within 340 ms of each other at ~37.5 s, all `200`, while the backend API answered in 1.6–2.2 s and `browserTimings` showed `networkDuration` 16 ms against `processingDuration` 225 s. Every navigation Link now sets `prefetch={false}` — these routes are client components behind `ProtectedRoute` that fetch their own data, so the prefetched RSC payload carried no benefit. The doc also records that browser telemetry lives in a **separate** App Insights resource (`AUTOPILOT_MONITOR_WEB_APPINSIGHTS_ID`) that the MCP `query_backend_logs` tool cannot reach, which is why the freezes left no trace in the backend logs.
+* **Creation**: Added `web/portal-navigation-prefetch.md` (and a `Web Portal` section to the index) — root cause of the minute-long portal freezes. `GlobalSidebar` and `Navbar` render the whole navigation on every page, so the App Router's default viewport prefetch issued one `?_rsc=` request per visible link against `portal.autopilotmonitor.com` (~10,400 in 14 days). *(The original entry attributed the freeze to HTTP/1.1 and a six-connection-per-origin cap — see the 2026-07-28 correction; the queue is server-side.)* When the Static Web Apps managed runtime queued the prefetches (p50 91 ms, p95 896 ms, but max 234 s / 21 samples over 30 s), the navigation the user wanted was stuck behind that queue. Measured on the 2026-07-27 17:25 CEST incident: `/admin/presence?_rsc=` 151 s, three siblings finishing within 340 ms of each other at ~37.5 s, all `200`, while the backend API answered in 1.6–2.2 s and `browserTimings` showed `networkDuration` 16 ms against `processingDuration` 225 s. Every navigation Link now sets `prefetch={false}` — these routes are client components behind `ProtectedRoute` that fetch their own data, so the prefetched RSC payload carried no benefit. The doc also records that browser telemetry lives in a **separate** App Insights resource (`AUTOPILOT_MONITOR_WEB_APPINSIGHTS_ID`) that the MCP `query_backend_logs` tool cannot reach, which is why the freezes left no trace in the backend logs.
 
 * **Creation**: Added `backend/rule-regression-radar.md` — F3 regression radar (analyze rules only; gather rules wait for their per-batch stats dedup fix): per (tenant, rule) daily hit rate from `RuleStats`, firing only when the trailing 7-day window has ≥5 hit sessions and ≥20 evaluated sessions, the rate is ≥2× the prior 28-day baseline AND the Wilson 95 % intervals are disjoint (deterministic `MetricsMath` primitive with hand-computed test vectors). Suppressed for deleted rules, rules younger than baseline+window (`CreatedAt` grace), rules edited inside the window (`UpdatedAt`), empty baselines, and the `RuleRegressionRadarDisabled` app-setting kill switch. Alert episodes live as `ruleregression|{ruleId}` tracker rows (one bell + one `RuleFrequencyRegression` ops event per episode; numbers refreshed while active; re-armed under 1.5× baseline, on fire-stop, or by the 30-day tracker retention). On-fire dimension correlation over osBuild/model/agentVersion/imeVersion with the "correlated, not necessarily causal" wording contract. Surfaces: `regressions[]` in the rule-stats response (MCP inherits), the analyze-rules page's 30-day sparkline and regression badge.
 

docs/mcp/tool-telemetry.md

@@ -0,0 +1,81 @@
+---
+type: concept
+title: MCP Tool Telemetry
+description: The three telemetry layers for judging MCP tool quality — backend App Insights via X-MCP-Tool-Name, the per-user usage table, and the MCP_TOOL_LOGGING stderr lines that carry the signals the backend cannot see (soft errors, result size vs. cap, zero-hit searches, Zod rejections).
+resource: src/McpServer/autopilot-monitor-mcp/src/telemetry.ts
+tags: [mcp, telemetry, observability, tool-quality]
+timestamp: 2026-08-05
+---
+
+# Schema
+
+Three layers answer "are the MCP tools doing their job, and are tools missing?":
+
+1. **Backend App Insights** — every tool handler runs inside `withToolTelemetry`
+   (`src/telemetry.ts`), which propagates the tool name via AsyncLocalStorage so
+   `apiFetch` stamps `X-MCP-Tool-Name` on each backend request.
+   `RequestTelemetryMiddleware` copies it into the request telemetry as
+   `McpToolName`: per-tool call volume, latency percentiles and HTTP failure
+   rates by KQL. Blind spot: tools that never call the backend, and handler-level
+   soft errors (see layer 3).
+2. **Usage table** — `McpQuotaEnforcementMiddleware.TrackUsage` counts per
+   user/day under the key `toolname:endpoint`; surfaced by the `get_api_usage`
+   tool. Counts only, every call counts as success.
+3. **stderr JSON lines** (`MCP_TOOL_LOGGING=true`, queryable via Container App
+   Logs) — the layer that carries what the other two structurally cannot:
+   - `tool_call`: duration, `isError` **including soft errors** (handlers never
+     throw — `toolError` *returns* `isError: true`, so backend-only telemetry
+     records those calls as successes), `resultChars` + `overCap` (result
+     exceeds the tool's `anthropic/maxResultSizeChars` hint → the host truncates
+     it; a frequently-overCap tool needs tighter defaults or projections), a
+     size-bounded args summary, and the caller scope (ga/delegated/tenant).
+     This is the ONLY telemetry for backend-free tools: `search_docs`,
+     `validate_rule`, `get_resource`, the local ranking of `search_knowledge`.
+   - `search_zero_hit`: query text (capped) whenever `search_events` /
+     `search_knowledge` / `search_docs` return zero results — the most direct
+     "missing docs / missing knowledge / missing tool?" demand signal.
+   - `tool_call_rejected`: rejections the SDK answers *before* any handler runs
+     (Zod argument validation, unknown/disabled tool). Two non-obvious facts,
+     both found by live verification: SDK 1.30 wraps these McpErrors as a
+     *successful* JSON-RPC response whose result is `{ isError: true, text:
+     "MCP error <code>: …" }` — a JSON-RPC error envelope never exists for
+     them — and the Hono bridge (`getRequestListener`) may stream the body as
+     `res.write` chunks with a bare `res.end()`. The sniffer in the `/mcp`
+     route therefore wraps both `write` and `end`, reassembles up to 10 KB and
+     matches both shapes (`attachToolCallRejectionSniffer` in `telemetry.ts`).
+     Handler soft errors never carry the `MCP error` prefix, so they are not
+     double-logged. This is the strongest "the schema or description confuses
+     the model" signal and was previously invisible everywhere.
+
+The env flag defaults to `true` in `infra/mcp-server.bicep` (documented desired
+state — the template is not routinely deployed; the live flag is set with
+`az containerapp update --set-env-vars MCP_TOOL_LOGGING=true`).
+
+# Examples
+
+Count zero-hit queries to find unmet demand (Log Analytics):
+
+```kusto
+ContainerAppConsoleLogs_CL
+| where Log_s has '"type":"search_zero_hit"'
+| extend d = parse_json(Log_s)
+| summarize count() by tostring(d.tool), tostring(d.query)
+```
+
+Per-tool soft-error and truncation rates:
+
+```kusto
+ContainerAppConsoleLogs_CL
+| where Log_s has '"type":"tool_call"'
+| extend d = parse_json(Log_s)
+| summarize calls = count(), errors = countif(d.isError == true),
+            overCap = countif(d.overCap == true), p95ms = percentile(tolong(d.durationMs), 95)
+  by tool = tostring(d.tool)
+```
+
+# Citations
+
+- `src/McpServer/autopilot-monitor-mcp/src/telemetry.ts` — wrapper + log emitters
+- `src/McpServer/autopilot-monitor-mcp/src/index.ts` — `/mcp` rejection sniffer
+- `src/Backend/AutopilotMonitor.Functions/Middleware/RequestTelemetryMiddleware.cs` — `McpToolName` stamping
+- `src/Backend/AutopilotMonitor.Functions/Middleware/McpQuotaEnforcementMiddleware.cs` — usage-table counting

docs/rules/gather-rule-phase-scoping.md

@@ -8,7 +8,7 @@ tags:
   - backend
   - gather-rules
   - config
-timestamp: 2026-07-20T00:00:00+02:00
+timestamp: 2026-08-04T00:00:00+02:00
 ---
 
 # Problem
@@ -64,6 +64,35 @@ enter-rule and an exit-rule on the same phase never cannibalise each other's slo
 * Old agents do not know the trigger value and simply never fire the rule (silent no-op) —
   which is why `phase_exit` needs no ConfigVersion bump: no new field is transported.
 
+# Which "phase" feeds the triggers — the emitted timeline, not raw signals
+
+The phase the executor sees is fed by `GatherRuleExecutorHost` from the **post-reduce
+`TimelineEventStream`**: `EventTimelineEmitter` publishes every emitted event's
+`(eventType, phase)` after the decision engine reduced the originating signal. Phase triggers
+therefore fire exactly when the UI timeline shows the phase — by construction.
+
+This replaced the original V2 wiring (`SignalIngress.SignalPosted`), which fires at enqueue
+time with the **raw** collector payload. The raw phase can run minutes ahead of the
+engine-declared one: in session `32312a32` (RealmJoin tenant) the Shell-Core ESP-exit
+synthesized `EspPhaseChanged(FinalizingSetup)` at 12:18, while the engine — holding the
+transition behind the RealmJoin completion gate until the first deployment resolved — declared
+`phase_transition(FinalizingSetup)` at 12:25. A `phase_change` rule on `FinalizingSetup`
+reading `HKLM\SOFTWARE\RealmJoin\Custom\BIOS` fired 7 minutes early and read the key before
+the RealmJoin package wrote it (`exists=false`).
+
+Consequences of the emitted-event feed:
+
+* `phase_change` / `phase_exit` / phase **scope** gates all follow the engine-reduced phase
+  (single feed, consistent with the portal's "collects once when the enrollment reaches …").
+* `on_event` now sees **every emitted event type**, including engine-emitted ones
+  (`enrollment_complete`, `phase_transition`, `realmjoin_resolved`, …) that never existed on
+  the raw signal stream — the documented "On Event with `enrollment_complete`" end-of-enrollment
+  pattern only works because of this. This restores V1 semantics (V1 fired triggers from every
+  emitted `EnrollmentEvent`).
+* Other hosts (`DeviceInfoHost`, `UserEspKeepAwakeHost`, `ProvisioningPackageHost`) still key
+  off the raw signal stream deliberately — their collections are about OS state at the raw
+  boundary (ESP exit, keep-awake), not about timeline agreement.
+
 # Scope semantics (agent, `GatherRuleExecutor`)
 
 * Scope applies to **all trigger types**:
@@ -130,7 +159,9 @@ enter-rule and an exit-rule on the same phase never cannibalise each other's slo
 # Citations
 
 * `src/Agent/AutopilotMonitor.Agent.V2.Core/Monitoring/Telemetry/Gather/GatherRuleExecutor.cs` — scope gates, latch, canonical hash
+* `src/Agent/AutopilotMonitor.Agent.V2.Core/Orchestration/Hosts/GatherRuleExecutorHost.cs` — timeline-event trigger feed
+* `src/Agent/AutopilotMonitor.Agent.V2.Core/Orchestration/TimelineEventStream.cs` — post-reduce observer surface
 * `src/Backend/AutopilotMonitor.Functions/Functions/Rules/GatherRulesFunction.cs` — `ValidateScopeAndEmitMode`
 * `src/Backend/AutopilotMonitor.Functions/Services/GatherRuleService.cs` — partial-PUT merge, `ContentEquivalent`
 * `src/Shared/AutopilotMonitor.Shared/Models/Rules/GatherRule.cs` — field contracts
-* Tests: `GatherRuleExecutorPhaseScopeTests`, `GatherRuleExecutorEmitModeTests` (agent); `GatherRuleUpdatePartialMergeTests`, `GatherRuleScopeFieldsTests` (backend)
+* Tests: `GatherRuleExecutorPhaseScopeTests`, `GatherRuleExecutorEmitModeTests`, `GatherRuleExecutorHostTimelineFeedTests` (agent); `GatherRuleUpdatePartialMergeTests`, `GatherRuleScopeFieldsTests` (backend)

docs/rules/rule-authoring-surface.md

@@ -0,0 +1,152 @@
+---
+type: Concept
+title: Rule Authoring Surface — MCP Resources, validate_rule, and the Analyze Dry-Run
+description: >-
+  How customer AIs author gather/analyze rules against the real contract: the baked
+  authoring resources (guide, schemas, guardrails) generated by combine.js, the
+  MCP-local validate_rule pre-flight, and the side-effect-free backend dry-run that
+  traces a draft analyze rule against one session's events.
+resource: src/McpServer/autopilot-monitor-mcp/src/tools/rules.ts
+tags: [rules, mcp, analyze-rules, gather-rules, dry-run, authoring]
+timestamp: 2026-08-05
+---
+
+# Concept
+
+Customers author rules with an AI connected to the MCP server. Retrieval
+(`search_docs`) is deliberately NOT the knowledge source for authoring: chunked
+top-K retrieval can silently omit an operator, a guardrail prefix, or an enum,
+and the AI then produces a plausible-but-dead rule. The authoring surface is
+therefore **deterministic**: three `get_resource` entries carry the complete
+contract, a local validator rejects what production would reject or silently
+ignore, and a backend dry-run evaluates a draft against real session events with
+a full trace.
+
+The intended loop: draft → `validate_rule` → `test_analyze_rule` against a real
+session (one that should fire, one that should not) → iterate → create in the
+portal. The `author-rule` MCP prompt walks a client through exactly this order.
+
+# Schema
+
+## Resources (deterministic authoring context)
+
+| Resource | Content | Source |
+| --- | --- | --- |
+| `rule_authoring_guide` | Hand-written complete authoring knowledge: collector types, triggers, condition sources, operators, confidence model incl. the exact factor DSL, `{{token}}` interpolation order, guardrail matching semantics, pitfalls | `src/rule-authoring-guide.ts` |
+| `rule_schemas` | Both JSON Schemas (2020-12) verbatim | generated |
+| `rule_guardrails` | `rules/guardrails.json` verbatim | generated |
+
+Generation: `node rules/scripts/combine.js` bakes schemas + guardrails into
+`src/McpServer/autopilot-monitor-mcp/src/rule-authoring.generated.ts` (same
+pattern as the web's `utils/guardrails.generated.ts`; the tsconfig `rootDir` and
+the Docker build's exclusion of `rules/schema` rule out importing the JSON
+directly). Drift is closed twice: CI's `guardrails-in-sync` job re-runs
+combine.js and fails on any diff, and `rule-authoring-drift.test.ts` pins
+generated == repo source plus guide enums == schema enums.
+
+## validate_rule (MCP-local)
+
+`src/rule-validation.ts`, no backend call. Three layers:
+
+1. **Schema** — ajv (draft 2020-12) against the baked schemas, validating the
+   single-rule `$defs` entry directly (the top-level oneOf wrapper would double
+   every error).
+2. **Guardrails** — mirrors the AGENT's matching semantics from
+   `GatherRuleGuards.cs` (see [gather-rule-guardrails.md](gather-rule-guardrails.md)):
+   hive-stripped segment-bounded registry/file prefixes, whitespace-bounded WMI
+   prefixes, EXACT command matching, `/`-bounded event-log channels, and the
+   code-enforced hard blocks (`Security` etc. channels, `C:\Users`,
+   `C:\Windows\System32\config`).
+3. **Semantic lint** — schema-valid-but-dead rules: unreachable
+   confidenceThreshold, factor conditions outside the three parseable shapes
+   (`exists`, `count >= N`, `phase_duration > N`), unknown event types (warning;
+   `gather_*` softened to info), unanchored `not_regex` allow-lists,
+   unresolvable `{{token}}`s, trigger cross-fields, outputEventType
+   convention/collision checks.
+
+The validator is advisory pre-flight only — the agent re-enforces guardrails
+on-device and the backend re-validates structure. It must never be stricter
+than production.
+
+## POST /api/rules/analyze/dryrun (backend)
+
+`DryRunAnalyzeRuleFunction` → `RuleEngine.DryRunRuleAsync`. Body
+`{ sessionId, rule }` (draft `AnalyzeRule`, 1 MB cap). Policy tier
+`TenantAdminOrGlobalReader` — a POST by shape but a pure read in effect, so the
+read-only Global Reader is admitted; platform-scope callers reach any tenant's
+session via `FindSessionTenantIdAsync` (same pattern as `GetRuleResultsFunction`).
+
+`RuleEngine.DryRun.cs` is a partial-class trace twin of `EvaluateRule`: it
+shares the exact evaluators (`EvaluatePrecondition` / `EvaluateCondition` /
+`EvaluateConfidenceFactor`) but evaluates **all** conditions instead of breaking
+on the first failed required one — the full picture is the point of a dry run.
+Verdicts: `fired`, `skipped_by_precondition`, `required_condition_not_met`,
+`no_conditions_matched`, `below_confidence_threshold`, `no_events`. Each
+condition entry carries `matched`, the production evidence dictionary (or the
+evaluator's reason string) and `matchingEventCount` — how many session events
+even have that eventType, the first thing to check on an unexpected miss.
+
+Invariants, pinned by `RuleEngineDryRunTests`:
+
+* **Parity**: verdict `fired` ⇔ `EvaluateRule` produces a result, with identical
+  confidence and evidence keys. Factor evaluation stays sequential against the
+  accumulating `matchedConditions` (a factor can observe earlier `factor_*`
+  entries) — reordering would change results.
+* **Side-effect freedom**: exactly one strict event read; never a RuleResult
+  write, never `TryMarkSessionFailedFromRuleAsync`, never a notification.
+  `wouldMarkSessionAsFailed` is reported, not acted on.
+
+`test_analyze_rule` (MCP) wraps the endpoint and adds the interpolated
+explanation/remediation preview via the existing `interpolate-rule-template.ts`
+against the returned `matchedConditions`.
+
+## POST /api/rules/gather/test-pattern (backend)
+
+The logparser counterpart to the analyze dry-run, added after a field incident:
+a customer verified a logparser regex with a PHP tester and the agent's .NET
+engine matched differently. `TestLogPatternFunction` evaluates a pattern against
+pasted sample lines with the AGENT's exact matching semantics:
+
+* Regex construction identical to `LogParserCollector`: `Compiled`, 1 s timeout,
+  **no IgnoreCase** — logparser matching is case-sensitive (unlike analyze-rule
+  regex conditions, which run IgnoreCase).
+* `format` behaves exactly like the rule parameter: `cmtrace` (default) parses
+  each line via the shared `CmTraceLogParser` and matches against the parsed
+  MESSAGE only; `text` matches the raw line. First match per line
+  (`Regex.Match`), group `"0"` excluded, unsuccessful groups omitted — the
+  returned `groups` are exactly the event-data fields the device would emit.
+* Mirrors the agent's diagnostics: per-line outcomes
+  (`matched | no_match | parse_failed | regex_timeout`), the all-lines-parse-fail
+  hint ("set parameter format=text") verbatim, and a case-sensitivity note on
+  zero matches.
+* Pure compute on the request body — no tenant data touched. Same policy tier
+  as the dry-run (`TenantAdminOrGlobalReader`); caps: 200 lines, 8 KB/line,
+  1 MB body.
+
+Parity is structural, not duplicated: `CmTraceLogParser` moved from the agent
+(`Monitoring/Enrollment/Ime`) to **Shared** (`AutopilotMonitor.Shared.Logging`)
+so agent and backend run the SAME parsing implementation. Timestamp caveat:
+bias-less CMTrace lines parse with `AssumeLocal`, which on the backend is the
+server's timezone — the endpoint therefore reports match/parse results, never
+timestamps. `test_log_pattern` (MCP) wraps the endpoint; `validate_rule`
+additionally lints logparser parameters (missing/non-compiling pattern, unknown
+format value) and its `nextStep` routes logparser drafts to `test_log_pattern`.
+
+## What is deliberately absent
+
+* **No gather-rule remote execution** — gather rules run as SYSTEM on devices;
+  session dry-run is analyze-only. Logparser authors get the pattern tester
+  above; all gather authors get guardrail pre-flight plus the on-device debug
+  log ([gather-rule-debug-log](../agent/gather-rule-debug-log.md)).
+* **No rule write/deploy via MCP** — creating rules stays in the portal.
+
+# Citations
+
+* `src/Backend/AutopilotMonitor.Functions/Functions/Rules/TestLogPatternFunction.cs` — logparser pattern tester
+* `src/Shared/AutopilotMonitor.Shared/Logging/CmTraceLogParser.cs` — shared CMTrace parser (agent + backend)
+* `src/Backend/AutopilotMonitor.Functions/Services/RuleEngine.DryRun.cs` — trace twin + DTOs
+* `src/Backend/AutopilotMonitor.Functions/Functions/Rules/DryRunAnalyzeRuleFunction.cs` — endpoint + draft validation
+* `src/McpServer/autopilot-monitor-mcp/src/rule-validation.ts` — validator
+* `src/McpServer/autopilot-monitor-mcp/src/tools/rules.ts` — validate_rule / test_analyze_rule
+* `src/McpServer/autopilot-monitor-mcp/src/rule-authoring-guide.ts` — guide resource
+* `rules/scripts/combine.js` — MCP module generation

docs/url-registry.md

@@ -21,7 +21,7 @@ literal appears nowhere else.
 | Component | Registry | Guard test |
 |---|---|---|
 | C# (Shared/Backend/Agent) | `AutopilotMonitor.Shared.Constants` (`*BaseUrl`) | `HardcodedUrlGuardTests` |
-| Web | `utils/config.ts` (`DOCS_URL`, `SITE_URL`, `PORTAL_URL`, `ENTRA_LOGIN_URL`, `API_URL_PROD`, `BLOB_URL_PROD`, `AGENT_DOWNLOAD_HOSTNAMES`) | `utils/__tests__/hardcodedUrls.guard.test.ts` |
+| Web | `utils/config.ts` (`DOCS_URL`, `SITE_URL`, `PORTAL_URL`, `BOOTSTRAP_GO_URL`, `ENTRA_LOGIN_URL`, `API_URL_PROD`, `BLOB_URL_PROD`, `AGENT_DOWNLOAD_HOSTNAMES`) | `utils/__tests__/hardcodedUrls.guard.test.ts` |
 | MCP | `src/config.ts` (`API_BASE_URL`, `ENTRA_LOGIN_BASE_URL`, `DOCS_BASE_URL`) | `src/__tests__/hardcoded-urls.guard.test.ts` |
 
 Derived registries build on these instead of repeating hosts:
@@ -76,6 +76,42 @@ Deliberately still on the legacy account: the `HealthCheckService` /
 `build-agent.yml` — they exist precisely to keep already-deployed customer
 bootstrap scripts working until the customer migration completes.
 
+# Bootstrap go-URL (2026-07-28)
+
+The OOBE bootstrap short-URL moved from `www.autopilotmonitor.com/go/{code}`
+(Next.js route, SSR) to **`go.autopilotmonitor.com/{code}`** — a Front Door
+custom domain whose `/*` route rewrites onto `/api/bootstrap/go/{code}` on the
+Function App (`GetBootstrapScriptFunction`). Registry entries:
+`Constants.BootstrapGoBaseUrl` (C#, the single producer via
+`CreateBootstrapSessionFunction`) and `BOOTSTRAP_GO_URL` (web, display-only in
+the sessions list); `go.autopilotmonitor.com` is on both guards' enforced-host
+lists. `CreateBootstrapSessionUrlShapeTests` pins the produced URL as an
+independent oracle — before this, no test guarded the bootstrap URL shape at
+all.
+
+Front Door route caching for `bootstrap-go` is DISABLED — same hazard class as
+the `/agent/*` route above, sharpened: the script body inlines the bearer
+token, so a cache hit would replay one requester's token to another.
+`NoStoreCacheMiddleware` additionally stamps `no-store` via the
+`/api/bootstrap/go/` prefix.
+
+Transition COMPLETED with the static-export PR (2026-07-29): the legacy
+Next.js `/go/[code]` route, `utils/bootstrapValidation.ts`, and
+`middleware.ts` are deleted — verified safe because the BootstrapSessions
+table held zero active sessions predating the URL cutover (all expired
+2026-03). The backend is now the only script producer;
+`OobeBootstrapScriptGeneratorTests`' golden file remains as the pin of the
+shipped template.
+
+Portal detail routes are query-string based since the same PR
+(`/sessions?id=…` etc., builders in `lib/routes.ts`, notification producer
+`Constants.PortalSessionUrl`). Legacy PATH-shaped links in sent
+Teams/Slack/webhook notifications are rewritten forever by SWA wildcard
+rewrites + `components/LegacyPathRedirect.tsx`; `staticwebapp.config.json`
+carries the production redirects/headers and is guarded by
+`utils/__tests__/swaConfig.guard.test.ts` (registry-backed hosts, no
+unsafe-eval, route order).
+
 # Citations
 
 - `src/Shared/AutopilotMonitor.Shared/Constants.cs` — C# registry

docs/web/portal-navigation-prefetch.md

@@ -1,7 +1,7 @@
 ---
 type: Concept
 title: Portal Navigation Prefetch & the SWA Runtime Bottleneck
-description: Why every navigation Link in the portal sets prefetch={false} — the App Router's viewport prefetch fires one RSC request per visible link against an HTTP/1.1 Static Web Apps runtime, and its latency tail starves the connection pool that serves the document and the route chunks.
+description: Why every navigation Link in the portal sets prefetch={false} — the App Router's viewport prefetch fires one RSC request per visible link, and the Static Web Apps SSR runtime queues them server-side into a multi-minute latency tail. Also records what the follow-up measurement showed about the Standard SKU and the keep-alive side effect.
 resource: src/Web/autopilot-monitor-web/components/GlobalSidebar.tsx
 tags:
   - web
@@ -25,21 +25,26 @@ it enters the viewport.
 
 # Mechanism
 
-Three properties combine into a portal-wide freeze:
+Two properties combine into a portal-wide freeze:
 
 1. **Fan-out.** The navigation is fully rendered on each page load, so a single navigation issues one
    RSC request per visible link — measured at ~10,400 requests over 14 days.
-2. **Shared origin over HTTP/1.1.** `portal.autopilotmonitor.com` serves the document, the JS route
-   chunks *and* the RSC payloads, and it negotiates HTTP/1.1 — not HTTP/2. Browsers cap concurrent
-   connections per origin at six.
-3. **A heavy latency tail on the SSR runtime.** RSC responses are prerendered and edge-cached
+2. **A heavy latency tail on the SSR runtime.** RSC responses are prerendered and edge-cached
    (`x-nextjs-cache: HIT`, `s-maxage=31536000`), so the median is fast. On a cache miss or cold start
-   the Static Web Apps managed runtime queues them.
+   the Static Web Apps managed runtime queues them **server-side**, and the queue drains all at once.
 
-When the tail hits, the in-flight prefetches hold all six connections. The document request and the
-route chunks of the page the user actually wants then have no socket available, and the tab shows a
-loading spinner or a blank page until the queue drains. Nothing fails — the requests eventually
-return `200`, which is why the failure leaves no error trace anywhere.
+The navigation the user wants is then stuck behind that queue and the tab shows a loading spinner or a
+blank page until it drains. Nothing fails — the requests eventually return `200`, which is why the
+failure leaves no error trace anywhere.
+
+> **Correction (2026-07-28).** The original version of this document named a third property: that
+> `portal.autopilotmonitor.com` negotiates HTTP/1.1 and the prefetches exhaust the six-connection
+> browser cap. **That is wrong.** It came from `curl -w '%{http_version}'` on a Windows build of curl
+> whose Schannel backend has no HTTP/2 support, so it can only ever report `1.1`. ALPN says otherwise:
+> `openssl s_client -alpn h2,http/1.1` negotiates **h2** on the portal host, confirmed by a .NET
+> `HttpClient` request returning `HTTP/2.0`. There is no six-connection cap and connection starvation
+> was never the mechanism — the queue is server-side. Verify HTTP versions with `openssl s_client
+> -alpn` or `HttpClient`, never with this curl build.
 
 # Evidence
 
@@ -62,6 +67,39 @@ document immediately and the browser then waited nearly four minutes for the `lo
 Fourteen-day distribution of RSC prefetches: n = 10,428, p50 = 91 ms, p95 = 896 ms, max = 234,230 ms,
 38 over 10 s, 21 over 30 s.
 
+# Outcome, measured 2026-07-28
+
+Two changes landed within half an hour of each other on 2026-07-27: the SWA plan went Free → Standard
+at 16:02:44 UTC, and `prefetch={false}` went live at 16:34:13 UTC. Twenty hours of production
+telemetry separate their effects.
+
+**The Standard plan produced no measurable latency gain.** Latency is governed almost entirely by the
+gap to the previous request — the SSR runtime cools down — so raw percentiles only measure the traffic
+mix. Stratified by that gap, the two eras are indistinguishable (p50, Free → Standard): `<10s`
+85 → 95 ms · `10-60s` 100 → 117 ms · `1-5min` 295 → 310 ms · `5-30min` 429 → 441 ms. Tail rates match
+too: Free ran 1.64 % over 2 s and 0.374 % over 10 s (n = 10,163); Standard produced 6 and 1 events at
+n = 258 against 4.2 and 1.0 expected. `browserTimings.totalDuration` by Mann-Whitney: n = 436 vs 48,
+z = −0.24, **p = 0.81**.
+
+**The prefetch fix is what removed the freezes** — worst `browserTimings.totalDuration` fell from
+225,277 ms to 4,856 ms, and the 30-second events stopped.
+
+**It also removed an accidental keep-alive.** The prefetch storm kept the SSR runtime warm: 85 % of
+requests used to arrive less than 10 s apart, now 46 % do. On an identical never-cacheable route
+(`/sessions/{id}`) the median rose from 87 ms to 211 ms and p90 from 465 ms to 1,480 ms. After 517
+minutes idle, one request took 11,441 ms and was abandoned (`resultCode 0`). The trade — minute-long
+freezes gone, ~150 ms added to a cold navigation — is worth it, but it is a trade.
+
+Do not benchmark this with a synthetic burst. Firing requests in quick succession warms the runtime
+and measures the best case: in a 25-round `curl --parallel-max 6` run, round 1 came in at p50 288 ms
+and rounds 4–25 at p50 113 ms.
+
+> **Endgame (2026-07-29).** The cold-start class was eliminated at the root: the portal became a
+> full static export (`output: 'export'`) — the SWA-managed SSR runtime no longer exists, so there
+> is nothing left to cool down. One escalation drove this: on 2026-07-28 a cold start exceeded the
+> SWA's 45-second function limit and the landing page served a hard "Backend call failure" 500.
+> The availability test that bridged the gap as a keep-alive stays as plain uptime monitoring.
+
 # Diagnosing this class of problem
 
 The backend Application Insights resource is the wrong place to look — a freeze appears there as an

infra/mcp-server.bicep

@@ -60,8 +60,8 @@ param apiUrl string = 'https://autopilotmonitor-api-eu.azurewebsites.net'
 @description('Container image tag')
 param imageTag string = 'latest'
 
-@description('Entra ID app registration client_id used for the OAuth proxy. Public value (appears in JWT aud claim); not a secret.')
-param entraClientId string = '1a400946-62c1-4ab4-aa37-f730ac89704d'
+@description('Entra ID app registration client_id used for the OAuth proxy. Public value (appears in JWT aud claim); not a secret. Since the C4A8 app-reg move this is the NEW app (the old 1a400946-… app remains valid at the backend for legacy-homed tenants).')
+param entraClientId string = '886ab5e2-6144-442c-80cc-9b28e0667731'
 
 @secure()
 @description('Entra ID client secret for OAuth token exchange')
@@ -80,8 +80,8 @@ param mcpPublicUrl string = ''
 @description('Base64-encoded HMAC key (>=32 bytes after decode) for signing the OAuth proxy state. Naming and format match the backend\'s PaginationTokenSigningKey for consistency. Empty = generate per-instance random key on startup (acceptable for single-replica deployments since state has 10 min lifetime). Generate with PowerShell: [Convert]::ToBase64String([Security.Cryptography.RandomNumberGenerator]::GetBytes(32))')
 param oAuthStateSigningKey string = ''
 
-@description('Enable structured tool-call logging to stderr (queryable via Container App Logs)')
-param toolLoggingEnabled bool = false
+@description('Enable structured tool-call logging to stderr (queryable via Container App Logs). Volume is one small JSON line per tool call - negligible at current usage.')
+param toolLoggingEnabled bool = true
 
 // --- Azure Container Registry ---
 

rules/analyze/ANALYZE-SEC-008.json

@@ -0,0 +1,78 @@
+{
+  "$schema": "../schema/analyze-rule.schema.json",
+  "ruleId": "ANALYZE-SEC-008",
+  "title": "Secure Boot is disabled",
+  "description": "Detects devices enrolling with Secure Boot turned off. Secure Boot is a firmware-level protection against boot-time malware and is a prerequisite for several Windows security features (VBS/Credential Guard, device health attestation) and common Intune compliance policies. Devices that support Secure Boot but have it disabled should be flagged during enrollment. Legacy BIOS devices (no Secure Boot capability) are excluded — the agent marks those with a note field when the SecureBoot registry state key is absent.",
+  "severity": "warning",
+  "category": "security",
+  "version": "1.0.0",
+  "author": "Autopilot Monitor",
+  "enabled": true,
+  "trigger": "single",
+  "baseConfidence": 70,
+  "preconditions": [
+    {
+      "source": "event_data",
+      "eventType": "secureboot_status",
+      "dataField": "note",
+      "operator": "not_exists",
+      "value": "",
+      "description": "Skip when the agent could not find the SecureBoot state registry key (note field set) — that indicates a legacy BIOS / non-UEFI device where Secure Boot is unsupported rather than disabled, so a warning would not be actionable."
+    }
+  ],
+  "conditions": [
+    {
+      "signal": "secureboot_disabled",
+      "source": "event_data",
+      "eventType": "secureboot_status",
+      "dataField": "uefiSecureBootEnabled",
+      "operator": "equals",
+      "value": "false",
+      "required": true
+    },
+    {
+      "signal": "physical_device",
+      "source": "event_data",
+      "eventType": "hardware_spec",
+      "dataField": "isVirtualMachine",
+      "operator": "equals",
+      "value": "false",
+      "required": false
+    }
+  ],
+  "confidenceFactors": [
+    { "signal": "physical_device", "condition": "exists", "weight": 20 }
+  ],
+  "confidenceThreshold": 60,
+  "explanation": "This device enrolled with **Secure Boot disabled**.\n\nThe firmware reports UEFI mode, but Secure Boot is turned off (`HKLM\\SYSTEM\\CurrentControlSet\\Control\\SecureBoot\\State\\UEFISecureBootEnabled = 0`). Without Secure Boot the boot chain is not verified, which:\n\n- Leaves the device exposed to bootkits and unsigned boot-time code\n- Blocks or weakens Virtualization-based Security (VBS), Credential Guard and Device Health Attestation\n- Typically makes the device **non-compliant** if an Intune compliance policy requires Secure Boot — Conditional Access may then block the user right after enrollment\n\nSecure Boot is usually disabled deliberately in firmware setup (e.g. for imaging, dual-boot or legacy CSM mode) and simply never re-enabled before the device was handed to Autopilot.",
+  "remediation": [
+    {
+      "title": "Enable Secure Boot in UEFI firmware",
+      "steps": [
+        "Reboot into the UEFI firmware setup (typically F2/F10/F12/Del during boot, or Shift+Restart -> Troubleshoot -> UEFI Firmware Settings)",
+        "Disable Legacy/CSM boot mode if it is active — Secure Boot requires native UEFI boot",
+        "Enable Secure Boot and ensure the Microsoft UEFI CA keys are selected (factory default key set)",
+        "Save, reboot and verify in Windows: msinfo32 -> 'Secure Boot State' = On, or PowerShell Confirm-SecureBootUEFI returns True",
+        "For Hyper-V test VMs: use a Generation 2 VM and enable Secure Boot in the VM's Security settings (template 'Microsoft Windows')"
+      ]
+    },
+    {
+      "title": "Check compliance impact",
+      "steps": [
+        "Review Intune compliance policies assigned to this device for a 'Require Secure Boot' setting",
+        "If the device stays non-compliant, Conditional Access policies may block sign-in — fix firmware settings before user handover"
+      ]
+    }
+  ],
+  "relatedDocs": [
+    {
+      "title": "Microsoft Learn: Secure Boot",
+      "url": "https://learn.microsoft.com/en-us/windows-hardware/design/device-experiences/oem-secure-boot"
+    },
+    {
+      "title": "Microsoft Learn: Re-enable Secure Boot",
+      "url": "https://learn.microsoft.com/en-us/windows-hardware/manufacture/desktop/disabling-secure-boot"
+    }
+  ],
+  "tags": ["security", "secureboot", "firmware", "uefi", "compliance"]
+}

rules/dist/analyze-rules.json

@@ -2687,6 +2687,93 @@
         "truncated",
         "coverage"
       ]
+    },
+    {
+      "ruleId": "ANALYZE-SEC-008",
+      "title": "Secure Boot is disabled",
+      "description": "Detects devices enrolling with Secure Boot turned off. Secure Boot is a firmware-level protection against boot-time malware and is a prerequisite for several Windows security features (VBS/Credential Guard, device health attestation) and common Intune compliance policies. Devices that support Secure Boot but have it disabled should be flagged during enrollment. Legacy BIOS devices (no Secure Boot capability) are excluded — the agent marks those with a note field when the SecureBoot registry state key is absent.",
+      "severity": "warning",
+      "category": "security",
+      "version": "1.0.0",
+      "author": "Autopilot Monitor",
+      "enabled": true,
+      "trigger": "single",
+      "baseConfidence": 70,
+      "preconditions": [
+        {
+          "source": "event_data",
+          "eventType": "secureboot_status",
+          "dataField": "note",
+          "operator": "not_exists",
+          "value": "",
+          "description": "Skip when the agent could not find the SecureBoot state registry key (note field set) — that indicates a legacy BIOS / non-UEFI device where Secure Boot is unsupported rather than disabled, so a warning would not be actionable."
+        }
+      ],
+      "conditions": [
+        {
+          "signal": "secureboot_disabled",
+          "source": "event_data",
+          "eventType": "secureboot_status",
+          "dataField": "uefiSecureBootEnabled",
+          "operator": "equals",
+          "value": "false",
+          "required": true
+        },
+        {
+          "signal": "physical_device",
+          "source": "event_data",
+          "eventType": "hardware_spec",
+          "dataField": "isVirtualMachine",
+          "operator": "equals",
+          "value": "false",
+          "required": false
+        }
+      ],
+      "confidenceFactors": [
+        {
+          "signal": "physical_device",
+          "condition": "exists",
+          "weight": 20
+        }
+      ],
+      "confidenceThreshold": 60,
+      "explanation": "This device enrolled with **Secure Boot disabled**.\n\nThe firmware reports UEFI mode, but Secure Boot is turned off (`HKLM\\SYSTEM\\CurrentControlSet\\Control\\SecureBoot\\State\\UEFISecureBootEnabled = 0`). Without Secure Boot the boot chain is not verified, which:\n\n- Leaves the device exposed to bootkits and unsigned boot-time code\n- Blocks or weakens Virtualization-based Security (VBS), Credential Guard and Device Health Attestation\n- Typically makes the device **non-compliant** if an Intune compliance policy requires Secure Boot — Conditional Access may then block the user right after enrollment\n\nSecure Boot is usually disabled deliberately in firmware setup (e.g. for imaging, dual-boot or legacy CSM mode) and simply never re-enabled before the device was handed to Autopilot.",
+      "remediation": [
+        {
+          "title": "Enable Secure Boot in UEFI firmware",
+          "steps": [
+            "Reboot into the UEFI firmware setup (typically F2/F10/F12/Del during boot, or Shift+Restart -> Troubleshoot -> UEFI Firmware Settings)",
+            "Disable Legacy/CSM boot mode if it is active — Secure Boot requires native UEFI boot",
+            "Enable Secure Boot and ensure the Microsoft UEFI CA keys are selected (factory default key set)",
+            "Save, reboot and verify in Windows: msinfo32 -> 'Secure Boot State' = On, or PowerShell Confirm-SecureBootUEFI returns True",
+            "For Hyper-V test VMs: use a Generation 2 VM and enable Secure Boot in the VM's Security settings (template 'Microsoft Windows')"
+          ]
+        },
+        {
+          "title": "Check compliance impact",
+          "steps": [
+            "Review Intune compliance policies assigned to this device for a 'Require Secure Boot' setting",
+            "If the device stays non-compliant, Conditional Access policies may block sign-in — fix firmware settings before user handover"
+          ]
+        }
+      ],
+      "relatedDocs": [
+        {
+          "title": "Microsoft Learn: Secure Boot",
+          "url": "https://learn.microsoft.com/en-us/windows-hardware/design/device-experiences/oem-secure-boot"
+        },
+        {
+          "title": "Microsoft Learn: Re-enable Secure Boot",
+          "url": "https://learn.microsoft.com/en-us/windows-hardware/manufacture/desktop/disabling-secure-boot"
+        }
+      ],
+      "tags": [
+        "security",
+        "secureboot",
+        "firmware",
+        "uefi",
+        "compliance"
+      ]
     }
   ]
 }

rules/scripts/combine.js

@@ -161,3 +161,45 @@ ${flatArray(guardrails.blockedEventLogChannels)}
 } else {
   console.warn('guardrails.json not found — skipping guardrails generation');
 }
+
+// ── MCP rule-authoring module generation ────────────────────────────────────
+// The MCP server exposes the rule schemas + guardrails as get_resource content
+// so a customer's AI can author rules against the real contract instead of
+// retrieval fragments. The server's tsconfig (rootDir: src, no resolveJsonModule)
+// and the Docker build (rules/schema not copied) rule out importing the JSON
+// directly — so we bake it into a TS module, exactly like the web mirror above.
+// CI's guardrails-in-sync job re-runs this script and fails on any diff, which
+// makes drift between rules/* and this generated module impossible to merge.
+
+const mcpAuthoringOutput = path.resolve(
+  rulesRoot, '..', 'src', 'McpServer', 'autopilot-monitor-mcp', 'src', 'rule-authoring.generated.ts'
+);
+
+{
+  const guardrails = JSON.parse(fs.readFileSync(guardrailsPath, 'utf8'));
+  const gatherSchema = JSON.parse(fs.readFileSync(path.join(rulesRoot, 'schema', 'gather-rule.schema.json'), 'utf8'));
+  const analyzeSchema = JSON.parse(fs.readFileSync(path.join(rulesRoot, 'schema', 'analyze-rule.schema.json'), 'utf8'));
+
+  const ts = `/**
+ * AUTO-GENERATED from rules/guardrails.json + rules/schema/*.schema.json — DO NOT EDIT.
+ * Run: node rules/scripts/combine.js
+ *
+ * Consumed by the MCP server's rule-authoring surface (get_resource +
+ * validate_rule): the JSON Schemas are the validation contract, the guardrails
+ * are the agent-side collection allowlists. Single source of truth is rules/;
+ * the CI guardrails-in-sync job guards this file against drift.
+ */
+
+/** JSON Schema (2020-12) for gather rules — rules/schema/gather-rule.schema.json verbatim. */
+export const GATHER_RULE_SCHEMA: Record<string, unknown> = ${JSON.stringify(gatherSchema, null, 2)};
+
+/** JSON Schema (2020-12) for analyze rules — rules/schema/analyze-rule.schema.json verbatim. */
+export const ANALYZE_RULE_SCHEMA: Record<string, unknown> = ${JSON.stringify(analyzeSchema, null, 2)};
+
+/** Gather-rule collection guardrails — rules/guardrails.json verbatim. */
+export const RULE_GUARDRAILS = ${JSON.stringify(guardrails, null, 2)} as const;
+`;
+
+  fs.writeFileSync(mcpAuthoringOutput, ts, 'utf8');
+  console.log('rule-authoring.generated.ts: schemas + guardrails baked for MCP server');
+}

scripts/Bootstrap/Install-AutopilotMonitor-dev.Tests.ps1

@@ -0,0 +1,307 @@
+# Pester tests (Pester 5+) for the bootstrap guard/relax logic in
+# Install-AutopilotMonitor-dev.ps1 (v2.3-dev).
+#
+# The script under test is dot-sourced; its entry guard prevents the bootstrap
+# from executing, so loading it here is side-effect free. External state (WMI,
+# registry, filesystem, WinRT) is mocked; profile directories are real folders
+# under Pester's $TestDrive with a manipulated CreationTimeUtc.
+#
+# Run under Windows PowerShell 5.1 to match the IME runtime:
+#   powershell.exe -NoProfile -Command "& { $c = New-PesterConfiguration; $c.Run.Path = 'scripts\Bootstrap'; $c.Output.Verbosity = 'Detailed'; Invoke-Pester -Configuration $c }"
+#
+# This file MUST remain pure ASCII (PS 5.1 reads BOM-less files as ANSI).
+
+BeforeAll {
+    . (Join-Path $PSScriptRoot 'Install-AutopilotMonitor-dev.ps1')
+
+    function New-FakeProfile {
+        param([string]$Name, [double]$AgeMinutes)
+        $p = Join-Path $TestDrive $Name
+        New-Item -ItemType Directory -Path $p -Force | Out-Null
+        (Get-Item $p).CreationTimeUtc = (Get-Date).ToUniversalTime().AddMinutes(-$AgeMinutes)
+        return $p
+    }
+}
+
+Describe 'Test-IsCloudPc' {
+    # Marker set captured 2026-08-06 from a real W365 Enterprise Cloud PC: local WMI
+    # is generic ('Virtual Machine'), so detection rests on the Windows365 registry
+    # key AND the CloudManagedDesktopExtension service (both required).
+    BeforeEach {
+        Mock Write-Log { }
+        Mock Get-CimInstance { [pscustomobject]@{ Manufacturer = 'Microsoft Corporation'; Model = 'Virtual Machine' } }
+    }
+
+    It 'detects a Cloud PC when both markers are present' {
+        Mock Test-Path { $true } -ParameterFilter { $Path -eq 'HKLM:\SOFTWARE\Microsoft\Windows365' }
+        Mock Get-Service { [pscustomobject]@{ Name = 'CloudManagedDesktopExtension'; Status = 'Running' } }
+        Test-IsCloudPc | Should -BeTrue
+    }
+
+    It 'does not detect with the registry key alone (e.g. W365-Boot physical client)' {
+        Mock Test-Path { $true } -ParameterFilter { $Path -eq 'HKLM:\SOFTWARE\Microsoft\Windows365' }
+        Mock Get-Service { $null }
+        Test-IsCloudPc | Should -BeFalse
+    }
+
+    It 'does not detect with the service alone' {
+        Mock Test-Path { $false } -ParameterFilter { $Path -eq 'HKLM:\SOFTWARE\Microsoft\Windows365' }
+        Mock Get-Service { [pscustomobject]@{ Name = 'CloudManagedDesktopExtension'; Status = 'Running' } }
+        Test-IsCloudPc | Should -BeFalse
+    }
+
+    It 'does not detect a plain device (no markers)' {
+        Mock Test-Path { $false } -ParameterFilter { $Path -eq 'HKLM:\SOFTWARE\Microsoft\Windows365' }
+        Mock Get-Service { $null }
+        Test-IsCloudPc | Should -BeFalse
+    }
+
+    It 'still evaluates markers when the WMI identity query fails' {
+        Mock Get-CimInstance { throw 'RPC server unavailable' }
+        Mock Test-Path { $true } -ParameterFilter { $Path -eq 'HKLM:\SOFTWARE\Microsoft\Windows365' }
+        Mock Get-Service { [pscustomobject]@{ Name = 'CloudManagedDesktopExtension'; Status = 'Running' } }
+        Test-IsCloudPc | Should -BeTrue
+    }
+}
+
+Describe 'Get-OobeState' {
+    It 'returns a non-empty state string and never throws' {
+        Get-OobeState | Should -Not -BeNullOrEmpty
+    }
+}
+
+Describe 'Get-RealUserProfilePaths' {
+    BeforeEach {
+        Mock Write-Log { }
+    }
+
+    It 'merges WMI and filesystem views, drops special/system profiles, dedupes' {
+        Mock Get-CimInstance {
+            @(
+                [pscustomobject]@{ Special = $false; LocalPath = 'C:\Users\LeonGottschalk' }
+                [pscustomobject]@{ Special = $true; LocalPath = 'C:\Users\systemprofile' }
+                [pscustomobject]@{ Special = $false; LocalPath = 'D:\Profiles\Elsewhere' }
+            )
+        }
+        Mock Get-ChildItem {
+            @(
+                [pscustomobject]@{ FullName = 'C:\Users\LeonGottschalk' }
+                [pscustomobject]@{ FullName = 'C:\Users\Public' }
+                [pscustomobject]@{ FullName = 'C:\Users\defaultuser0' }
+                [pscustomobject]@{ FullName = 'C:\Users\WDAGUtilityAccount' }
+            )
+        }
+        $result = @(Get-RealUserProfilePaths)
+        $result | Should -Be @('C:\Users\LeonGottschalk')
+    }
+
+    It 'falls back to the filesystem view when the WMI query fails' {
+        Mock Get-CimInstance { throw 'WMI broken' }
+        Mock Get-ChildItem {
+            @(
+                [pscustomobject]@{ FullName = 'C:\Users\SomeUser' }
+                [pscustomobject]@{ FullName = 'C:\Users\Default' }
+            )
+        }
+        $result = @(Get-RealUserProfilePaths)
+        $result | Should -Be @('C:\Users\SomeUser')
+    }
+
+    It 'returns an empty result when only special/system profiles exist' {
+        Mock Get-CimInstance { @() }
+        Mock Get-ChildItem {
+            @(
+                [pscustomobject]@{ FullName = 'C:\Users\Public' }
+                [pscustomobject]@{ FullName = 'C:\Users\defaultuser1' }
+            )
+        }
+        @(Get-RealUserProfilePaths).Count | Should -Be 0
+    }
+}
+
+Describe 'Get-RelaxDecision' {
+    BeforeEach {
+        Mock Write-Log { }
+        # Defaults: physical device, OOBE long done. Individual tests override.
+        Mock Get-OobeState { 'Completed' }
+        Mock Test-IsCloudPc { $false }
+    }
+
+    Context 'Windows 365 Cloud PC' {
+        BeforeEach {
+            Mock Test-IsCloudPc { $true }
+        }
+
+        It 'relaxes for a single fresh profile although OOBE is Completed (W365 field case)' {
+            $p = New-FakeProfile 'LeonGottschalk' 0.6
+            $d = Get-RelaxDecision -ProfilePaths @($p) -OobeProfileMaxAgeMinutes 15
+            $d.Active | Should -BeTrue
+            $d.IsCloudPc | Should -BeTrue
+        }
+
+        It 'does not relax for an old profile (productive Cloud PC)' {
+            $p = New-FakeProfile 'LeonGottschalk' 30
+            (Get-RelaxDecision -ProfilePaths @($p) -OobeProfileMaxAgeMinutes 15).Active | Should -BeFalse
+        }
+
+        It 'does not relax for two profiles' {
+            $p1 = New-FakeProfile 'UserA' 2
+            $p2 = New-FakeProfile 'UserB' 400
+            (Get-RelaxDecision -ProfilePaths @($p1, $p2) -OobeProfileMaxAgeMinutes 15).Active | Should -BeFalse
+        }
+
+        It 'relaxes even when the WinRT OOBE API is unavailable (old build)' {
+            Mock Get-OobeState { 'Unavailable' }
+            $p = New-FakeProfile 'CpcUser' 1
+            (Get-RelaxDecision -ProfilePaths @($p) -OobeProfileMaxAgeMinutes 15).Active | Should -BeTrue
+        }
+
+        It 'does not relax for a profile with a future creation time (clock skew)' {
+            $p = New-FakeProfile 'SkewUser' -10
+            (Get-RelaxDecision -ProfilePaths @($p) -OobeProfileMaxAgeMinutes 15).Active | Should -BeFalse
+        }
+    }
+
+    Context 'OOBE InProgress (Windows Backup for Organizations, v2.2 behaviour)' {
+        It 'relaxes for a single fresh profile during OOBE' {
+            Mock Get-OobeState { 'InProgress' }
+            $p = New-FakeProfile 'RestoreUser' 3
+            $d = Get-RelaxDecision -ProfilePaths @($p) -OobeProfileMaxAgeMinutes 15
+            $d.Active | Should -BeTrue
+        }
+    }
+
+    Context 'no trigger' {
+        It 'does not relax on a physical device with a fresh profile and OOBE Completed' {
+            $p = New-FakeProfile 'SomeUser' 2
+            (Get-RelaxDecision -ProfilePaths @($p) -OobeProfileMaxAgeMinutes 15).Active | Should -BeFalse
+        }
+
+        It 'stays inactive with no profiles at all' {
+            (Get-RelaxDecision -ProfilePaths @() -OobeProfileMaxAgeMinutes 15).Active | Should -BeFalse
+        }
+    }
+}
+
+Describe 'Get-BootstrapDecision' {
+    BeforeEach {
+        Mock Write-Log { }
+        # Baseline: clean device during Device ESP -- no marker, no profiles, no
+        # logged-on user, 1h uptime, agent not installed. Tests override selectively.
+        Mock Get-ItemProperty { $null }
+        Mock Get-RealUserProfilePaths { @() }
+        Mock Get-OobeState { 'Completed' }
+        Mock Test-IsCloudPc { $false }
+        Mock Get-CimInstance { [pscustomobject]@{ LastBootUpTime = (Get-Date).AddHours(-1) } } -ParameterFilter { $ClassName -eq 'Win32_OperatingSystem' }
+        $script:cleanAgentBin = Join-Path $TestDrive 'AgentBin'
+    }
+
+    It 'installs on a clean ESP device' {
+        $d = Get-BootstrapDecision -MaxBootstrapWindowHours 12 -OobeProfileMaxAgeMinutes 15 -AgentBinPath $script:cleanAgentBin
+        $d.Install | Should -BeTrue
+        $d.ReasonCode | Should -BeNullOrEmpty
+        $d.RelaxActive | Should -BeFalse
+    }
+
+    It 'skips when the Deployed marker exists (guard 1)' {
+        Mock Get-ItemProperty { [pscustomobject]@{ Deployed = '2026-08-01T10:00:00Z' } } -ParameterFilter { $Path -eq 'HKLM:\SOFTWARE\AutopilotMonitor' }
+        $d = Get-BootstrapDecision -MaxBootstrapWindowHours 12 -OobeProfileMaxAgeMinutes 15 -AgentBinPath $script:cleanAgentBin
+        $d.Install | Should -BeFalse
+        $d.ReasonCode | Should -Be 'AlreadyDeployed'
+    }
+
+    It 'skips a productive device with an old profile (guard 2)' {
+        $script:fakeProfile = New-FakeProfile 'OldUser' 5000
+        Mock Get-RealUserProfilePaths { @($script:fakeProfile) }
+        $d = Get-BootstrapDecision -MaxBootstrapWindowHours 12 -OobeProfileMaxAgeMinutes 15 -AgentBinPath $script:cleanAgentBin
+        $d.Install | Should -BeFalse
+        $d.ReasonCode | Should -Be 'ProfilesFound'
+    }
+
+    It 'installs on a freshly provisioned Cloud PC with one fresh profile (W365 field case)' {
+        $script:fakeProfile = New-FakeProfile 'LeonGottschalk' 0.6
+        Mock Get-RealUserProfilePaths { @($script:fakeProfile) }
+        Mock Test-IsCloudPc { $true }
+        # First-connect user is already visible in LogonUI on W365 -- must not block either.
+        Mock Get-ItemProperty { [pscustomobject]@{ LastLoggedOnUser = 'AzureAD\LeonGottschalk' } } -ParameterFilter { $Path -like '*LogonUI*' }
+        $d = Get-BootstrapDecision -MaxBootstrapWindowHours 12 -OobeProfileMaxAgeMinutes 15 -AgentBinPath $script:cleanAgentBin
+        $d.Install | Should -BeTrue
+        $d.RelaxActive | Should -BeTrue
+    }
+
+    It 'skips when a real user has logged on and no relax applies (guard 3)' {
+        Mock Get-ItemProperty { [pscustomobject]@{ LastLoggedOnUser = 'AzureAD\SomeUser' } } -ParameterFilter { $Path -like '*LogonUI*' }
+        $d = Get-BootstrapDecision -MaxBootstrapWindowHours 12 -OobeProfileMaxAgeMinutes 15 -AgentBinPath $script:cleanAgentBin
+        $d.Install | Should -BeFalse
+        $d.ReasonCode | Should -Be 'LastLoggedOnUser'
+    }
+
+    It 'does not skip for the defaultuser0 OOBE account (guard 3)' {
+        Mock Get-ItemProperty { [pscustomobject]@{ LastLoggedOnUser = 'defaultuser0' } } -ParameterFilter { $Path -like '*LogonUI*' }
+        (Get-BootstrapDecision -MaxBootstrapWindowHours 12 -OobeProfileMaxAgeMinutes 15 -AgentBinPath $script:cleanAgentBin).Install | Should -BeTrue
+    }
+
+    It 'skips when uptime exceeds the bootstrap window (guard 4)' {
+        Mock Get-CimInstance { [pscustomobject]@{ LastBootUpTime = (Get-Date).AddHours(-20) } } -ParameterFilter { $ClassName -eq 'Win32_OperatingSystem' }
+        $d = Get-BootstrapDecision -MaxBootstrapWindowHours 12 -OobeProfileMaxAgeMinutes 15 -AgentBinPath $script:cleanAgentBin
+        $d.Install | Should -BeFalse
+        $d.ReasonCode | Should -Be 'UptimeExceeded'
+    }
+
+    It 'installs on a Cloud PC despite uptime over the window when the relax is active (guard 4 exemption, v2.3-dev.3)' {
+        # W365 reality: provisioned days ago, running headless ever since; the user's
+        # first connect just created the profile. Uptime is meaningless here.
+        $script:fakeProfile = New-FakeProfile 'FirstConnectUser' 0.6
+        Mock Get-RealUserProfilePaths { @($script:fakeProfile) }
+        Mock Test-IsCloudPc { $true }
+        Mock Get-CimInstance { [pscustomobject]@{ LastBootUpTime = (Get-Date).AddHours(-90) } } -ParameterFilter { $ClassName -eq 'Win32_OperatingSystem' }
+        $d = Get-BootstrapDecision -MaxBootstrapWindowHours 12 -OobeProfileMaxAgeMinutes 15 -AgentBinPath $script:cleanAgentBin
+        $d.Install | Should -BeTrue
+        $d.RelaxActive | Should -BeTrue
+    }
+
+    It 'still skips an over-uptime Cloud PC when the relax is NOT active (no fresh profile)' {
+        Mock Test-IsCloudPc { $true }
+        Mock Get-CimInstance { [pscustomobject]@{ LastBootUpTime = (Get-Date).AddHours(-90) } } -ParameterFilter { $ClassName -eq 'Win32_OperatingSystem' }
+        $d = Get-BootstrapDecision -MaxBootstrapWindowHours 12 -OobeProfileMaxAgeMinutes 15 -AgentBinPath $script:cleanAgentBin
+        $d.Install | Should -BeFalse
+        $d.ReasonCode | Should -Be 'UptimeExceeded'
+    }
+
+    It 'keeps guard 4 for the OOBE-restore relax (physical device, uptime is meaningful)' {
+        $script:fakeProfile = New-FakeProfile 'RestoreUser' 3
+        Mock Get-RealUserProfilePaths { @($script:fakeProfile) }
+        Mock Get-OobeState { 'InProgress' }
+        Mock Get-CimInstance { [pscustomobject]@{ LastBootUpTime = (Get-Date).AddHours(-20) } } -ParameterFilter { $ClassName -eq 'Win32_OperatingSystem' }
+        $d = Get-BootstrapDecision -MaxBootstrapWindowHours 12 -OobeProfileMaxAgeMinutes 15 -AgentBinPath $script:cleanAgentBin
+        $d.Install | Should -BeFalse
+        $d.ReasonCode | Should -Be 'UptimeExceeded'
+    }
+
+    It 'skips when the agent binary is already present (guard 5)' {
+        $binPath = Join-Path $TestDrive 'AgentBinExisting'
+        New-Item -ItemType Directory -Path $binPath -Force | Out-Null
+        Set-Content -Path (Join-Path $binPath 'AutopilotMonitor.Agent.exe') -Value 'stub'
+        $d = Get-BootstrapDecision -MaxBootstrapWindowHours 12 -OobeProfileMaxAgeMinutes 15 -AgentBinPath $binPath
+        $d.Install | Should -BeFalse
+        $d.ReasonCode | Should -Be 'AgentPresent'
+    }
+}
+
+Describe 'logging purity' {
+    # Regression guard: Write-Log runs inside functions that RETURN decision
+    # objects. If it ever emits to the output stream again (Write-Output), the
+    # log lines leak into the return values and turn them into arrays. This
+    # test deliberately does NOT mock Write-Log.
+    It 'Get-BootstrapDecision returns exactly one object with real logging' {
+        Mock Get-ItemProperty { [pscustomobject]@{ Deployed = '2026-08-01T10:00:00Z' } } -ParameterFilter { $Path -eq 'HKLM:\SOFTWARE\AutopilotMonitor' }
+        # Plain local assignment: PowerShell's dynamic scoping makes Write-Log
+        # (called from Get-BootstrapDecision) resolve this $LogFile instead of
+        # the ProgramData path defined by the dot-sourced script.
+        $LogFile = Join-Path $TestDrive 'bootstrap_test.log'
+        $d = @(Get-BootstrapDecision -MaxBootstrapWindowHours 12 -OobeProfileMaxAgeMinutes 15 -AgentBinPath (Join-Path $TestDrive 'NoAgent'))
+        $d.Count | Should -Be 1
+        $d[0].ReasonCode | Should -Be 'AlreadyDeployed'
+        Get-Content $LogFile -Raw | Should -Match 'SKIP: Agent was previously deployed'
+    }
+}

scripts/Bootstrap/Install-AutopilotMonitor-dev.ps1

@@ -1,13 +1,24 @@
 <#
 .SYNOPSIS
-    Bootstrap script to deploy and start the Autopilot Monitor agent. (DEV)
+    DEV bootstrap script (v2.3-dev) to deploy and start the Autopilot Monitor agent.
 
 .DESCRIPTION
+    DEV VARIANT of Install-AutopilotMonitor.ps1 for validating the v2.3 Cloud-PC-relax
+    on Windows 365 before promoting it to the production script. Differences to v2.2:
+      - Cloud-PC-relax (see below) as a second trigger for the guard 2+3 exemption
+      - Raw OutOfBoxExperienceState value is logged (diagnosis)
+      - Logs to bootstrap_agent_dev.log so runs never interleave with the prod script
+      - Testable structure: guard/relax logic lives in functions; the script only
+        executes when run directly. Dot-sourcing it (as the Pester suite in
+        Install-AutopilotMonitor-dev.Tests.ps1 does) loads the functions without
+        side effects.
+
     Designed to be deployed via Intune as a PowerShell Script during Autopilot.
     Runs very early in the enrollment process (first Intune action) and:
       1. Runs pre-flight guards to skip productive devices and ghost re-installs.
-         An OOBE-relax exemption allows install when a single freshly-created profile
-         appears DURING OOBE (the "Windows Backup for Organizations" restore case).
+         A relax exemption allows install when a single freshly-created profile
+         appears DURING OOBE (Windows Backup for Organizations restore) or on a
+         freshly provisioned Windows 365 Cloud PC.
       2. Downloads the monitoring agent ZIP from Azure Blob Storage
       3. Verifies integrity via SHA-256 hash from the version manifest (mandatory)
       4. Extracts the agent into %ProgramData%\AutopilotMonitor\Agent
@@ -15,18 +26,36 @@
       6. Verifies the runtime process actually launched
     Agent self-destructs when enrollment completes.
 
-    OOBE-relax flow (guards 2+3): a real user profile (or a real LastLoggedOnUser)
-    normally means "productive -> skip". Windows Backup for Organizations breaks that
-    by restoring settings and creating ONE profile while still in OOBE. We relax guards
-    2+3 ONLY when all three positives hold, and nothing else:
-      (a) the OS positively reports OOBE InProgress (Test-OobeInProgress), AND
-      (b) there is exactly ONE real user profile, AND
-      (c) that profile was created within $OobeProfileMaxAgeMinutes minutes.
+    Relax flow (guards 2+3): a real user profile (or a real LastLoggedOnUser)
+    normally means "productive -> skip". Two legitimate flows break that assumption:
+
+    (1) Windows Backup for Organizations: one user signs in + restores DURING OOBE.
+        Trigger: the OS positively reports OOBE InProgress (Test via WinRT
+        SystemSetupInfo.OutOfBoxExperienceState).
+
+    (2) Windows 365 Cloud PC: W365 provisions headless -- OOBE and Intune enrollment
+        complete before any user ever connects, so OutOfBoxExperienceState is NEVER
+        InProgress when this script runs. The assigned user's profile is created at
+        first connect, typically seconds before IME pulls this script. Trigger: the
+        device positively identifies as a Cloud PC via TWO local markers (both
+        required; captured from a real Cloud PC -- local WMI reports only the
+        generic 'Virtual Machine' model): HKLM\SOFTWARE\Microsoft\Windows365
+        registry key AND the CloudManagedDesktopExtension service.
+
+    Either trigger relaxes guards 2+3 ONLY when additionally:
+      (a) there is exactly ONE real user profile, AND
+      (b) that profile was created within $OobeProfileMaxAgeMinutes minutes.
+    The Cloud PC trigger additionally exempts guard 4 (uptime window) -- see
+    .PARAMETER MaxBootstrapWindowHours for why boot uptime is meaningless there.
     Any miss keeps the original skip (SKIP-safe: we never install on uncertainty).
+    On productive devices the profile is old, so (b) keeps skipping correctly.
+    Known accepted edge: a W365 Frontline shared-mode device can legitimately show a
+    single fresh profile while productive; a mis-install there is one-time (agent
+    finds enrollment complete and self-destructs; Deployed marker prevents repeats).
 
 .PARAMETER AgentDownloadUrl
-    URL to download the agent ZIP from. Defaults to the production blob; override only
-    for parallel lab/dev assignments that point at a separate pre-release ZIP.
+    URL to download the agent ZIP from. Defaults to the production download endpoint;
+    override only for parallel lab/dev assignments that point at a separate pre-release ZIP.
 
 .PARAMETER VersionJsonName
     Filename of the integrity manifest in the same blob container as the agent ZIP.
@@ -36,11 +65,16 @@
     Maximum device uptime (hours) within which the bootstrap is still considered
     valid. Devices booted more than this many hours ago are skipped because we no
     longer trust their OOBE state. Default: 12.
+    Cloud PC note: NOT applied when the Cloud-PC relax is active. A Cloud PC runs
+    headless for days between provisioning and the user's first connect, and the
+    phase worth monitoring (Account Setup) only starts at that first connect --
+    there the fresh-profile window (OobeProfileMaxAgeMinutes) is the time anchor,
+    not boot uptime.
 
 .PARAMETER OobeProfileMaxAgeMinutes
-    Maximum age (minutes) of the single profile that may appear during OOBE for the
-    OOBE-relax exemption to apply. The restore->bootstrap gap is always minutes; an
-    older profile is treated as a productive device. Default: 15.
+    Maximum age (minutes) of the single profile that may appear for the relax
+    exemption to apply. The restore/first-connect -> bootstrap gap is always
+    minutes; an older profile is treated as a productive device. Default: 15.
 
 .NOTES
     - Agent is temporary and auto-removes after enrollment.
@@ -50,12 +84,34 @@
     - Scheduled Task survives reboots during enrollment.
     - OOBE detection uses Windows.System.Profile.SystemSetupInfo.OutOfBoxExperienceState.
       Requires Windows 10, version 1809 (introduced in 10.0.17763.0). Older builds lack
-      the class -> Test-OobeInProgress returns $false -> original (skip) behaviour. Docs:
+      the class -> state reads as 'Unavailable' -> original (skip) behaviour. Docs:
       https://learn.microsoft.com/en-us/uwp/api/windows.system.profile.systemsetupinfo
     - This script MUST remain pure ASCII (no Unicode/UTF-8 special chars).
       PowerShell 5.1 (IME) reads scripts without BOM as ANSI, corrupting multi-byte chars.
 
 .CHANGELOG
+    2026-08-06  v2.3-dev.3  Guard 4 (uptime window) exempted while the Cloud-PC relax is
+                      active: Cloud PCs run headless for days before the user's first
+                      connect, so boot uptime says nothing about enrollment freshness --
+                      the single-fresh-profile window (< OobeProfileMaxAgeMinutes) already
+                      anchors the relax in time. OOBE-restore keeps the uptime guard.
+    2026-08-06  v2.3-dev.2  Cloud PC detection rebuilt on captured evidence: first field
+                      test proved local WMI reports only Manufacturer='Microsoft
+                      Corporation' + Model='Virtual Machine' (the 'Cloud PC ...' model
+                      string exists only in Intune/Graph). Detection now requires the
+                      HKLM\SOFTWARE\Microsoft\Windows365 registry key AND the
+                      CloudManagedDesktopExtension service (both verified present on a
+                      real Cloud PC); raw identity + marker states are always logged.
+    2026-08-05  v2.3-dev  DEV variant (-dev.ps1, own log file bootstrap_agent_dev.log)
+                      to validate on Windows 365 before promotion to v2.3:
+                      Cloud-PC-relax -- a positively identified Cloud PC
+                      (Win32_ComputerSystem Manufacturer 'Microsoft Corporation' +
+                      Model 'Cloud PC*') now triggers the guard 2+3 relax alongside
+                      OOBE InProgress; the single-fresh-profile conditions are
+                      unchanged. Raw OutOfBoxExperienceState is now logged.
+                      Refactored into functions with a dot-source entry guard so the
+                      Pester suite (*.Tests.ps1) can load the logic without executing
+                      the bootstrap; behaviour when run directly is unchanged.
     2026-07-20  v2.2  Switched default download endpoint from the legacy blob
                       (autopilotmonitor.blob.core.windows.net) to the Front Door alias
                       https://download.autopilotmonitor.com/agent/ (route /agent/*).
@@ -69,16 +125,7 @@
     2026-05-09  v2.0  Generic bootstrap: agent owns its own defaults (e.g. 600 s
                       TenantId-wait), so the script only calls `--install` plain.
                       Hardened post-install with a 10 s runtime-process verify.
-    2026-04-09  v1.1  Introduced explicit script version, logged on startup.
-    2026-03-31        Replaced OS age + MDM pre-flight checks with multi-signal guard
-                      (registry deployment marker, WMI/filesystem user profile, last
-                      logged-on user, 12 h bootstrap window).
-    2026-03-30        Fixed non-ASCII characters that broke parsing under PowerShell 5.1.
-    2026-03-29        Hardened integrity check: SHA-256 verification via version.json.
-    2026-02-13        Simplified bootstrapper, introduced --install parameter for agent.
-    2026-02-12        Robust download with integrity check (Content-MD5), boot time support,
-                      pre-flight check to skip if agent already installed.
-    2026-02-05        Initial version.
+    (older entries: see Install-AutopilotMonitor.ps1)
 #>
 
 [CmdletBinding()]
@@ -97,97 +144,167 @@ param(
 )
 
 # Script version (bump on meaningful changes; see .CHANGELOG above)
-$ScriptVersion = "2.2"
+$ScriptVersion = "2.3-dev.3"
 
 # Configuration - Everything in ProgramData for easy cleanup
 $AgentBasePath = "$env:ProgramData\AutopilotMonitor"
 $AgentBinPath = "$AgentBasePath\Agent"
 $AgentLogPath = "$AgentBasePath\Logs"
-$LogFile = "$AgentLogPath\bootstrap_agent.log"
-
-New-Item -Path $AgentBasePath -ItemType Directory -Force -ErrorAction SilentlyContinue | Out-Null
-New-Item -Path $AgentBinPath -ItemType Directory -Force -ErrorAction SilentlyContinue | Out-Null
-New-Item -Path $AgentLogPath -ItemType Directory -Force -ErrorAction SilentlyContinue | Out-Null
+$LogFile = "$AgentLogPath\bootstrap_agent_dev.log"
 
+# Write-Host (NOT Write-Output): log calls happen inside functions that return
+# decision objects; Write-Output would leak every log line into those return
+# values and turn them into arrays. Write-Host goes to the console host only.
 function Write-Log {
     param([string]$Message)
     $timestamp = Get-Date -Format "yyyy-MM-dd HH:mm:ss"
     $logMessage = "[$timestamp] $Message"
-    Write-Output $logMessage
+    Write-Host $logMessage
     Add-Content -Path $LogFile -Value $logMessage -ErrorAction SilentlyContinue
 }
 
-# Positive OOBE check via the documented WinRT API
+# Raw OOBE state via the documented WinRT API
 # Windows.System.Profile.SystemSetupInfo.OutOfBoxExperienceState.
-# Returns $true ONLY when the OS reports InProgress. Any other state (Completed/NotStarted),
-# an older OS without the class (< Win10 1809 / 10.0.17763.0), or any error returns $false
+# Returns the state string (InProgress/Completed/NotStarted). An older OS without the
+# class (< Win10 1809 / 10.0.17763.0) or any error returns 'Unavailable'
 # -> SKIP-safe (we never relax a guard on uncertainty).
 # Docs: https://learn.microsoft.com/en-us/uwp/api/windows.system.profile.systemsetupinfo
-function Test-OobeInProgress {
+function Get-OobeState {
     try {
         $null = [Windows.System.Profile.SystemSetupInfo, Windows.System.Profile, ContentType = WindowsRuntime]
-        return ([Windows.System.Profile.SystemSetupInfo]::OutOfBoxExperienceState).ToString() -eq 'InProgress'
+        return ([Windows.System.Profile.SystemSetupInfo]::OutOfBoxExperienceState).ToString()
     }
     catch {
+        return 'Unavailable'
+    }
+}
+
+# Positive Windows 365 Cloud PC detection.
+# Evidence captured 2026-08-06 on a real, freshly provisioned W365 Enterprise Cloud PC:
+#   - Win32_ComputerSystem is GENERIC there: Manufacturer='Microsoft Corporation',
+#     Model='Virtual Machine'. The 'Cloud PC Enterprise ...' model string exists only
+#     in the Intune/Graph inventory, NOT in local WMI/SMBIOS -- it cannot be used here.
+#   - HKLM:\SOFTWARE\Microsoft\Windows365 exists.
+#   - Service 'CloudManagedDesktopExtension' (Microsoft Cloud Managed Desktop
+#     Extension, the W365 management agent that runs ON Cloud PCs) is installed.
+# BOTH markers are required (AND): each alone has plausible look-alikes (W365-Boot
+# physical clients may carry Windows365 policy state; the MCMD agent family also
+# served other managed-desktop offerings). Raw identity and both marker states are
+# always logged for field diagnosis; any error returns $false (SKIP-safe).
+function Test-IsCloudPc {
+    try {
+        $cs = Get-CimInstance Win32_ComputerSystem -ErrorAction Stop
+        Write-Log "Computer identity: Manufacturer='$($cs.Manufacturer)' Model='$($cs.Model)'."
+    }
+    catch { Write-Log "INFO: computer identity query failed: $($_.Exception.Message)" }
+
+    try {
+        $regMarker = Test-Path 'HKLM:\SOFTWARE\Microsoft\Windows365'
+        $svcMarker = $null -ne (Get-Service -Name 'CloudManagedDesktopExtension' -ErrorAction SilentlyContinue)
+        Write-Log "Cloud PC markers: Windows365 registry key=$regMarker; CloudManagedDesktopExtension service=$svcMarker."
+        return ($regMarker -and $svcMarker)
+    }
+    catch {
+        Write-Log "INFO: Cloud PC marker check failed: $($_.Exception.Message)"
         return $false
     }
 }
 
-try {
-    Write-Log "===== Autopilot Monitor Bootstrap Started ====="
-    Write-Log "Bootstrap script version: v$ScriptVersion"
+# Collects real (non-special) user profiles as full paths (WMI Special flag + filesystem).
+# NOTE: callers MUST wrap the result in @(...). PowerShell unrolls function output, so an
+# empty result returns $null and a single path returns a scalar string, whose [0] indexer
+# would yield its first char ('C') instead of the full path.
+function Get-RealUserProfilePaths {
+    $excludePattern = '^(defaultuser\d*|Public|Default( User)?|All Users|WDAGUtilityAccount)$'
+    @(
+        try {
+            Get-CimInstance Win32_UserProfile -ErrorAction Stop |
+                Where-Object { -not $_.Special -and $_.LocalPath -like 'C:\Users\*' } |
+                ForEach-Object { $_.LocalPath }
+        } catch { Write-Log "INFO: WMI profile query failed, continuing with filesystem check." }
+
+        (Get-ChildItem 'C:\Users' -Directory -ErrorAction SilentlyContinue).FullName
+    ) | Where-Object { $_ -and (Split-Path $_ -Leaf) -notmatch $excludePattern } |
+        Select-Object -Unique
+}
+
+# Relax: the ONLY exemption to guards 2+3. Two triggers (see .DESCRIPTION):
+#   (1) OOBE InProgress          -> Windows Backup for Organizations restore
+#   (2) Cloud PC identity        -> Windows 365 (headless OOBE, profile at first connect)
+# Either trigger additionally requires: exactly one real profile AND that profile
+# created < $OobeProfileMaxAgeMinutes minutes ago. Any miss keeps the original skip.
+# Returns an object with: Active (bool), OobeState (string), IsCloudPc (bool).
+function Get-RelaxDecision {
+    param(
+        [string[]]$ProfilePaths,
+        [int]$OobeProfileMaxAgeMinutes
+    )
+    if ($null -eq $ProfilePaths) { $ProfilePaths = @() }
+
+    $relaxActive = $false
+    $oobeState = Get-OobeState
+    $oobeInProgress = ($oobeState -eq 'InProgress')
+    $isCloudPc = Test-IsCloudPc
+    if ($isCloudPc) {
+        Write-Log "Cloud PC detected (OOBE state: $oobeState)."
+    }
+
+    $relaxTrigger = $null
+    if ($oobeInProgress) {
+        $relaxTrigger = "OOBE InProgress (Windows Backup restore case)"
+    } elseif ($isCloudPc) {
+        $relaxTrigger = "Cloud PC (headless provisioning, OOBE state: $oobeState)"
+    }
+
+    if ($ProfilePaths.Count -eq 1 -and $relaxTrigger) {
+        try {
+            $created = (Get-Item -LiteralPath $ProfilePaths[0] -Force -ErrorAction Stop).CreationTimeUtc
+            $ageMin = ((Get-Date).ToUniversalTime() - $created).TotalMinutes
+            if ($ageMin -ge 0 -and $ageMin -lt $OobeProfileMaxAgeMinutes) {
+                $relaxActive = $true
+                Write-Log ("Relax active: {0} + single profile created {1:N1}min ago (< {2}min). Guards 2+3 relaxed." -f $relaxTrigger, $ageMin, $OobeProfileMaxAgeMinutes)
+            } else {
+                Write-Log ("Relax NOT applied: {0} + single profile '{1}', but profile created {2:N1}min ago (created {3:u}) is outside the [0, {4})min window." -f $relaxTrigger, (Split-Path $ProfilePaths[0] -Leaf), $ageMin, $created, $OobeProfileMaxAgeMinutes)
+            }
+        } catch { Write-Log "INFO: profile age check failed; relax not applied. $($_.Exception.Message)" }
+    } elseif ($ProfilePaths.Count -eq 1) {
+        Write-Log "Relax NOT applied: single profile present but neither OOBE InProgress nor Cloud PC (OOBE state: $oobeState)."
+    } elseif ($ProfilePaths.Count -gt 1) {
+        Write-Log ("Relax NOT applied: {0} real profiles present (relax requires exactly one). OOBE state: {1}; CloudPC: {2}." -f $ProfilePaths.Count, $oobeState, $isCloudPc)
+    }
+
+    return [pscustomobject]@{
+        Active    = $relaxActive
+        OobeState = $oobeState
+        IsCloudPc = $isCloudPc
+    }
+}
+
+# Runs pre-flight guards 1-5 and returns the install decision WITHOUT side effects
+# beyond logging. Returns an object with:
+#   Install (bool), ReasonCode (null | AlreadyDeployed | ProfilesFound |
+#   LastLoggedOnUser | UptimeExceeded | AgentPresent), RelaxActive (bool).
+function Get-BootstrapDecision {
+    param(
+        [int]$MaxBootstrapWindowHours,
+        [int]$OobeProfileMaxAgeMinutes,
+        [string]$AgentBinPath
+    )
 
     # Guard 1: Agent was already deployed on this device (registry marker survives self-destruct)
     $deployed = (Get-ItemProperty -Path 'HKLM:\SOFTWARE\AutopilotMonitor' -Name 'Deployed' -ErrorAction SilentlyContinue).Deployed
     if ($deployed) {
         Write-Log "SKIP: Agent was previously deployed at $deployed."
-        exit 0
+        return [pscustomobject]@{ Install = $false; ReasonCode = 'AlreadyDeployed'; RelaxActive = $false }
     }
 
-    # Collect real (non-special) user profiles as full paths (WMI Special flag + filesystem).
-    $excludePattern = '^(defaultuser\d*|Public|Default( User)?|All Users|WDAGUtilityAccount)$'
-
-    # NOTE: the outer @() is required. Without it the trailing Where/Select pipeline
-    # unwraps a single result back to a scalar string, so $profilePaths[0] would index
-    # into the string and return its first char ('C') instead of the full path.
-    $profilePaths = @(
-        @(
-            try {
-                Get-CimInstance Win32_UserProfile -ErrorAction Stop |
-                    Where-Object { -not $_.Special -and $_.LocalPath -like 'C:\Users\*' } |
-                    ForEach-Object { $_.LocalPath }
-            } catch { Write-Log "INFO: WMI profile query failed, continuing with filesystem check." }
-
-            (Get-ChildItem 'C:\Users' -Directory -ErrorAction SilentlyContinue).FullName
-        ) | Where-Object { $_ -and (Split-Path $_ -Leaf) -notmatch $excludePattern } |
-            Select-Object -Unique
-    )
-
-    # OOBE-relax: the ONLY exemption to guards 2+3. Matches exactly the Windows Backup for
-    # Organizations restore (one user signs in + restores DURING OOBE). All three must hold:
-    #   OOBE InProgress  AND  exactly one profile  AND  that profile created < N minutes ago.
-    $oobeRelax = $false
-    $oobeInProgress = Test-OobeInProgress
-    if ($profilePaths.Count -eq 1 -and $oobeInProgress) {
-        try {
-            $created = (Get-Item -LiteralPath $profilePaths[0] -Force -ErrorAction Stop).CreationTimeUtc
-            $ageMin = ((Get-Date).ToUniversalTime() - $created).TotalMinutes
-            if ($ageMin -ge 0 -and $ageMin -lt $OobeProfileMaxAgeMinutes) {
-                $oobeRelax = $true
-                Write-Log ("OOBE-relax active: OOBE InProgress + single profile created {0:N1}min ago (< {1}min). Guards 2+3 relaxed (Windows Backup restore case)." -f $ageMin, $OobeProfileMaxAgeMinutes)
-            } else {
-                Write-Log ("OOBE-relax NOT applied: OOBE InProgress + single profile '{0}', but profile created {1:N1}min ago (created {2:u}) is outside the [0, {3})min window." -f (Split-Path $profilePaths[0] -Leaf), $ageMin, $created, $OobeProfileMaxAgeMinutes)
-            }
-        } catch { Write-Log "INFO: profile age check failed; OOBE-relax not applied. $($_.Exception.Message)" }
-    } elseif ($profilePaths.Count -eq 1 -and -not $oobeInProgress) {
-        Write-Log "OOBE-relax NOT applied: single profile present but OutOfBoxExperienceState != InProgress (OOBE already finished / not detectable)."
-    } elseif ($profilePaths.Count -gt 1) {
-        Write-Log ("OOBE-relax NOT applied: {0} real profiles present (relax requires exactly one)." -f $profilePaths.Count)
-    }
+    # The @() wrap is required, see NOTE on Get-RealUserProfilePaths.
+    $profilePaths = @(Get-RealUserProfilePaths)
+    $relax = Get-RelaxDecision -ProfilePaths $profilePaths -OobeProfileMaxAgeMinutes $OobeProfileMaxAgeMinutes
 
     # Guard 2: No real user profile should exist yet (primary productive-device guard),
-    # unless the OOBE-relax signature holds.
-    if ($profilePaths.Count -gt 0 -and -not $oobeRelax) {
+    # unless the relax signature holds.
+    if ($profilePaths.Count -gt 0 -and -not $relax.Active) {
         $details = (($profilePaths | ForEach-Object {
             $leaf = Split-Path $_ -Leaf
             try {
@@ -195,26 +312,36 @@ try {
                 "{0} (created {1:u}, {2:N1}min ago)" -f $leaf, $c, ((Get-Date).ToUniversalTime() - $c).TotalMinutes
             } catch { "$leaf (age unknown)" }
         }) | Select-Object -First 3) -join '; '
-        Write-Log "SKIP: Real user profile(s) found ($details). OOBE InProgress=$oobeInProgress. Device appears productive."
-        exit 0
+        Write-Log "SKIP: Real user profile(s) found ($details). OOBE state: $($relax.OobeState). CloudPC: $($relax.IsCloudPc). Device appears productive."
+        return [pscustomobject]@{ Install = $false; ReasonCode = 'ProfilesFound'; RelaxActive = $false }
     }
 
     # Guard 3: LastLoggedOnUser - during Device ESP no real user has logged on yet
-    # (same OOBE-relax exemption: the restoring user signs in during OOBE).
+    # (same relax exemption: the restoring/first-connect user signs in legitimately).
     $lastLoggedOnUser = (Get-ItemProperty -Path 'HKLM:\SOFTWARE\Microsoft\Windows\CurrentVersion\Authentication\LogonUI' -Name 'LastLoggedOnUser' -EA SilentlyContinue).LastLoggedOnUser
-    if ($lastLoggedOnUser -and $lastLoggedOnUser -notmatch 'defaultuser\d*' -and -not $oobeRelax) {
+    if ($lastLoggedOnUser -and $lastLoggedOnUser -notmatch 'defaultuser\d*' -and -not $relax.Active) {
         Write-Log "SKIP: LastLoggedOnUser found ($lastLoggedOnUser). Device appears productive."
-        exit 0
+        return [pscustomobject]@{ Install = $false; ReasonCode = 'LastLoggedOnUser'; RelaxActive = $false }
     }
 
     # Guard 4: Bootstrap window check - device uptime must be within accepted OOBE window.
     # Sleep/standby does not reset uptime, only real boot/restart does.
+    # Cloud PC exemption (v2.3-dev.3): a Cloud PC runs headless from provisioning until the
+    # user's first connect -- often days -- and the phase worth monitoring (Account Setup)
+    # only STARTS at that first connect. Boot uptime is therefore meaningless there; the
+    # single-fresh-profile window of the relax (< $OobeProfileMaxAgeMinutes min) is the time
+    # anchor instead. The OOBE-restore trigger keeps the original uptime guard (physical
+    # device, uptime is meaningful).
     $lastBoot = (Get-CimInstance Win32_OperatingSystem).LastBootUpTime
     $uptimeHours = ((Get-Date) - $lastBoot).TotalHours
     Write-Log "Device uptime: $([int]$uptimeHours)h (last boot: $lastBoot)"
     if ($uptimeHours -gt $MaxBootstrapWindowHours) {
-        Write-Log "SKIP: Device uptime is $([int]$uptimeHours)h. OOBE state is older than accepted bootstrap window of ${MaxBootstrapWindowHours}h."
-        exit 0
+        if ($relax.Active -and $relax.IsCloudPc) {
+            Write-Log "Uptime $([int]$uptimeHours)h exceeds the ${MaxBootstrapWindowHours}h window, but the Cloud PC relax is active (fresh first-connect profile is the time anchor). Continuing."
+        } else {
+            Write-Log "SKIP: Device uptime is $([int]$uptimeHours)h. OOBE state is older than accepted bootstrap window of ${MaxBootstrapWindowHours}h."
+            return [pscustomobject]@{ Install = $false; ReasonCode = 'UptimeExceeded'; RelaxActive = $relax.Active }
+        }
     }
 
     # Guard 5: Is the agent already installed? (leftover from previous run)
@@ -222,148 +349,175 @@ try {
         $existingAgent = Get-ChildItem -Path $AgentBinPath -Filter "AutopilotMonitor.Agent.exe" -ErrorAction SilentlyContinue
         if ($existingAgent) {
             Write-Log "SKIP: Agent already installed at $($existingAgent.FullName)."
+            return [pscustomobject]@{ Install = $false; ReasonCode = 'AgentPresent'; RelaxActive = $relax.Active }
+        }
+    }
+
+    return [pscustomobject]@{ Install = $true; ReasonCode = $null; RelaxActive = $relax.Active }
+}
+
+# Main bootstrap flow. Only invoked when the script is run directly (see entry guard
+# at the bottom); never on dot-source.
+function Invoke-Bootstrap {
+    try {
+        New-Item -Path $AgentBasePath -ItemType Directory -Force -ErrorAction SilentlyContinue | Out-Null
+        New-Item -Path $AgentBinPath -ItemType Directory -Force -ErrorAction SilentlyContinue | Out-Null
+        New-Item -Path $AgentLogPath -ItemType Directory -Force -ErrorAction SilentlyContinue | Out-Null
+
+        Write-Log "===== Autopilot Monitor Bootstrap Started ====="
+        Write-Log "Bootstrap script version: v$ScriptVersion"
+
+        $decision = Get-BootstrapDecision -MaxBootstrapWindowHours $MaxBootstrapWindowHours -OobeProfileMaxAgeMinutes $OobeProfileMaxAgeMinutes -AgentBinPath $AgentBinPath
+        if (-not $decision.Install) {
             exit 0
         }
-    }
 
-    Write-Log "Pre-flight checks passed -- no prior deployment, no productive-device signals, within bootstrap window (oobeRelax=$oobeRelax)"
+        Write-Log "Pre-flight checks passed -- no prior deployment, no productive-device signals, within bootstrap window (relaxActive=$($decision.RelaxActive))"
 
-    # Download and extract agent binaries
-    $agentExePath = Join-Path $AgentBinPath "AutopilotMonitor.Agent.exe"
+        # Download and extract agent binaries
+        $agentExePath = Join-Path $AgentBinPath "AutopilotMonitor.Agent.exe"
 
-    if (Test-Path $agentExePath) {
-        Write-Log "Agent already installed at $agentExePath"
-    }
-    else {
-        Write-Log "Downloading agent from $AgentDownloadUrl..."
-
-        try {
-            # Derive manifest URL from the agent download URL (same blob container)
-            $versionJsonUrl = $AgentDownloadUrl -replace '[^/]+$', $VersionJsonName
-            $expectedSha256 = $null
-            $manifestAttempts = 3
-            $manifestDelays = @(1, 2)   # short backoff between attempts; do not block enrollment
-
-            for ($attempt = 1; $attempt -le $manifestAttempts; $attempt++) {
-                try {
-                    Write-Log "Fetching $VersionJsonName (attempt ${attempt}/${manifestAttempts}) from $versionJsonUrl for integrity verification..."
-                    $versionJsonResponse = Invoke-RestMethod -Uri $versionJsonUrl -UseBasicParsing -TimeoutSec 5 -ErrorAction Stop
-                    if ($versionJsonResponse.sha256) {
-                        $expectedSha256 = $versionJsonResponse.sha256.ToLowerInvariant()
-                        Write-Log "SHA-256 hash from manifest: $expectedSha256 (version: $($versionJsonResponse.version))"
-                    } else {
-                        Write-Log "WARNING: Manifest has no sha256 field - integrity cannot be verified."
-                    }
-                    break   # manifest reached (with or without hash); retrying would not help
-                }
-                catch {
-                    Write-Log "WARNING: Could not fetch integrity manifest (attempt $attempt): $($_.Exception.Message)"
-                    if ($attempt -lt $manifestAttempts) {
-                        Start-Sleep -Seconds $manifestDelays[$attempt - 1]
-                    }
-                }
-            }
-
-            $zipPath = Join-Path $env:TEMP "AutopilotMonitor-Agent.zip"
-            $maxDownloadAttempts = 3
-            $downloadAttempt = 0
-
-            do {
-                $downloadAttempt++
-                try {
-                    Write-Log "Download attempt ${downloadAttempt}/${maxDownloadAttempts}"
-                    $downloadStopwatch = [System.Diagnostics.Stopwatch]::StartNew()
-                    Invoke-WebRequest `
-                        -Uri $AgentDownloadUrl `
-                        -OutFile $zipPath `
-                        -UseBasicParsing `
-                        -TimeoutSec 30 `
-                        -ErrorAction Stop
-                    $downloadStopwatch.Stop()
-                    $downloadSeconds = [math]::Round($downloadStopwatch.Elapsed.TotalSeconds, 1)
-                    Write-Log "Downloaded agent to $zipPath (took ${downloadSeconds}s)"
-                    break
-                }
-                catch {
-                    if ($downloadAttempt -ge $maxDownloadAttempts) {
-                        throw
-                    }
-
-                    $retryDelaysInSeconds = @(2, 4, 8)
-                    $retryDelaySeconds = $retryDelaysInSeconds[$downloadAttempt - 1]
-                    Write-Log "Download failed (attempt $downloadAttempt): $($_.Exception.Message). Retrying in ${retryDelaySeconds}s..."
-                    Start-Sleep -Seconds $retryDelaySeconds
-                }
-            } while ($downloadAttempt -lt $maxDownloadAttempts)
-
-            # SHA-256 from the version manifest is the only accepted integrity proof.
-            # No hash -> refuse to install an unverified ZIP (SKIP-safe security posture).
-            if (-not $expectedSha256) {
-                throw "No SHA-256 hash available from manifest - refusing to install unverified agent ZIP."
-            }
-            $actualSha256 = (Get-FileHash $zipPath -Algorithm SHA256).Hash.ToLowerInvariant()
-            Write-Log "Validating SHA-256 hash against manifest"
-            if ($actualSha256 -ne $expectedSha256) {
-                throw "SHA-256 integrity check FAILED. Expected='$expectedSha256', Actual='$actualSha256'. Download may be tampered or corrupted."
-            }
-            Write-Log "SHA-256 integrity check passed"
-
-            Expand-Archive -Path $zipPath -DestinationPath $AgentBinPath -Force
-            Write-Log "Extracted agent to $AgentBinPath"
-
-            Remove-Item $zipPath -Force -ErrorAction SilentlyContinue
-            Write-Log "Cleaned up temporary files"
-
-            if (-not (Test-Path $agentExePath)) {
-                throw "Agent executable not found after extraction at $agentExePath"
-            }
-
-            Write-Log "Agent installation completed successfully"
+        if (Test-Path $agentExePath) {
+            Write-Log "Agent already installed at $agentExePath"
         }
-        catch {
-            Write-Log "ERROR downloading/extracting agent: $($_.Exception.Message)"
-            throw
+        else {
+            Write-Log "Downloading agent from $AgentDownloadUrl..."
+
+            try {
+                # Derive manifest URL from the agent download URL (same blob container)
+                $versionJsonUrl = $AgentDownloadUrl -replace '[^/]+$', $VersionJsonName
+                $expectedSha256 = $null
+                $manifestAttempts = 3
+                $manifestDelays = @(1, 2)   # short backoff between attempts; do not block enrollment
+
+                for ($attempt = 1; $attempt -le $manifestAttempts; $attempt++) {
+                    try {
+                        Write-Log "Fetching $VersionJsonName (attempt ${attempt}/${manifestAttempts}) from $versionJsonUrl for integrity verification..."
+                        $versionJsonResponse = Invoke-RestMethod -Uri $versionJsonUrl -UseBasicParsing -TimeoutSec 5 -ErrorAction Stop
+                        if ($versionJsonResponse.sha256) {
+                            $expectedSha256 = $versionJsonResponse.sha256.ToLowerInvariant()
+                            Write-Log "SHA-256 hash from manifest: $expectedSha256 (version: $($versionJsonResponse.version))"
+                        } else {
+                            Write-Log "WARNING: Manifest has no sha256 field - integrity cannot be verified."
+                        }
+                        break   # manifest reached (with or without hash); retrying would not help
+                    }
+                    catch {
+                        Write-Log "WARNING: Could not fetch integrity manifest (attempt $attempt): $($_.Exception.Message)"
+                        if ($attempt -lt $manifestAttempts) {
+                            Start-Sleep -Seconds $manifestDelays[$attempt - 1]
+                        }
+                    }
+                }
+
+                $zipPath = Join-Path $env:TEMP "AutopilotMonitor-Agent.zip"
+                $maxDownloadAttempts = 3
+                $downloadAttempt = 0
+
+                do {
+                    $downloadAttempt++
+                    try {
+                        Write-Log "Download attempt ${downloadAttempt}/${maxDownloadAttempts}"
+                        $downloadStopwatch = [System.Diagnostics.Stopwatch]::StartNew()
+                        Invoke-WebRequest `
+                            -Uri $AgentDownloadUrl `
+                            -OutFile $zipPath `
+                            -UseBasicParsing `
+                            -TimeoutSec 30 `
+                            -ErrorAction Stop
+                        $downloadStopwatch.Stop()
+                        $downloadSeconds = [math]::Round($downloadStopwatch.Elapsed.TotalSeconds, 1)
+                        Write-Log "Downloaded agent to $zipPath (took ${downloadSeconds}s)"
+                        break
+                    }
+                    catch {
+                        if ($downloadAttempt -ge $maxDownloadAttempts) {
+                            throw
+                        }
+
+                        $retryDelaysInSeconds = @(2, 4, 8)
+                        $retryDelaySeconds = $retryDelaysInSeconds[$downloadAttempt - 1]
+                        Write-Log "Download failed (attempt $downloadAttempt): $($_.Exception.Message). Retrying in ${retryDelaySeconds}s..."
+                        Start-Sleep -Seconds $retryDelaySeconds
+                    }
+                } while ($downloadAttempt -lt $maxDownloadAttempts)
+
+                # SHA-256 from the version manifest is the only accepted integrity proof.
+                # No hash -> refuse to install an unverified ZIP (SKIP-safe security posture).
+                if (-not $expectedSha256) {
+                    throw "No SHA-256 hash available from manifest - refusing to install unverified agent ZIP."
+                }
+                $actualSha256 = (Get-FileHash $zipPath -Algorithm SHA256).Hash.ToLowerInvariant()
+                Write-Log "Validating SHA-256 hash against manifest"
+                if ($actualSha256 -ne $expectedSha256) {
+                    throw "SHA-256 integrity check FAILED. Expected='$expectedSha256', Actual='$actualSha256'. Download may be tampered or corrupted."
+                }
+                Write-Log "SHA-256 integrity check passed"
+
+                Expand-Archive -Path $zipPath -DestinationPath $AgentBinPath -Force
+                Write-Log "Extracted agent to $AgentBinPath"
+
+                Remove-Item $zipPath -Force -ErrorAction SilentlyContinue
+                Write-Log "Cleaned up temporary files"
+
+                if (-not (Test-Path $agentExePath)) {
+                    throw "Agent executable not found after extraction at $agentExePath"
+                }
+
+                Write-Log "Agent installation completed successfully"
+            }
+            catch {
+                Write-Log "ERROR downloading/extracting agent: $($_.Exception.Message)"
+                throw
+            }
         }
-    }
 
-    Write-Log "Calling agent install mode (--install)..."
-    & $agentExePath --install
-    $installExitCode = $LASTEXITCODE
-    if ($installExitCode -ne 0) {
-        throw "Agent install failed with exit code $installExitCode"
-    }
-    Write-Log "Agent install mode completed successfully"
+        Write-Log "Calling agent install mode (--install)..."
+        & $agentExePath --install
+        $installExitCode = $LASTEXITCODE
+        if ($installExitCode -ne 0) {
+            throw "Agent install failed with exit code $installExitCode"
+        }
+        Write-Log "Agent install mode completed successfully"
 
-    $runtimeProcessName = 'AutopilotMonitor.Agent'
-    $verifyTimeoutSec = 10
-    $verifyDeadline = (Get-Date).AddSeconds($verifyTimeoutSec)
-    $runtimeProc = $null
-    while ((Get-Date) -lt $verifyDeadline) {
-        $runtimeProc = Get-Process -Name $runtimeProcessName -ErrorAction SilentlyContinue | Select-Object -First 1
-        if ($null -ne $runtimeProc) { break }
-        Start-Sleep -Milliseconds 500
-    }
-    if ($null -ne $runtimeProc) {
-        $startedUtc = 'unavailable'
-        try { $startedUtc = $runtimeProc.StartTime.ToUniversalTime().ToString('o') } catch { }
-        Write-Log ("Runtime process verified: name={0}.exe pid={1} startedUtc={2}" -f $runtimeProcessName, $runtimeProc.Id, $startedUtc)
-    } else {
-        Write-Log ("WARNING: Runtime process verification FAILED. Agent --install reported success but no '{0}.exe' process appeared within {1}s. Likely silent block (AV/EDR, AppLocker/WDAC) of the runtime launch. Agent should still come up at next boot via the BootTrigger task. Check Event Viewer > Microsoft > Windows > TaskScheduler/Operational and AV/EDR logs for '{0}.exe'." -f $runtimeProcessName, $verifyTimeoutSec)
-    }
+        $runtimeProcessName = 'AutopilotMonitor.Agent'
+        $verifyTimeoutSec = 10
+        $verifyDeadline = (Get-Date).AddSeconds($verifyTimeoutSec)
+        $runtimeProc = $null
+        while ((Get-Date) -lt $verifyDeadline) {
+            $runtimeProc = Get-Process -Name $runtimeProcessName -ErrorAction SilentlyContinue | Select-Object -First 1
+            if ($null -ne $runtimeProc) { break }
+            Start-Sleep -Milliseconds 500
+        }
+        if ($null -ne $runtimeProc) {
+            $startedUtc = 'unavailable'
+            try { $startedUtc = $runtimeProc.StartTime.ToUniversalTime().ToString('o') } catch { }
+            Write-Log ("Runtime process verified: name={0}.exe pid={1} startedUtc={2}" -f $runtimeProcessName, $runtimeProc.Id, $startedUtc)
+        } else {
+            Write-Log ("WARNING: Runtime process verification FAILED. Agent --install reported success but no '{0}.exe' process appeared within {1}s. Likely silent block (AV/EDR, AppLocker/WDAC) of the runtime launch. Agent should still come up at next boot via the BootTrigger task. Check Event Viewer > Microsoft > Windows > TaskScheduler/Operational and AV/EDR logs for '{0}.exe'." -f $runtimeProcessName, $verifyTimeoutSec)
+        }
 
-    Write-Log "===== Bootstrap Completed Successfully ====="
+        Write-Log "===== Bootstrap Completed Successfully ====="
 
-    exit 0
+        exit 0
+    }
+    catch {
+        Write-Log "===== Bootstrap FAILED ====="
+        Write-Log "ERROR: $($_.Exception.Message)"
+        Write-Log "Stack trace: $($_.ScriptStackTrace)"
+        Write-Log "Please check log file: $LogFile"
+
+        $errMsg = "AutopilotMonitor bootstrap failed: $($_.Exception.Message)"
+        if ($errMsg.Length -gt 2048) { $errMsg = $errMsg.Substring(0, 1045) + '...' }
+        [Console]::Error.WriteLine($errMsg)
+
+        exit 1
+    }
 }
-catch {
-    Write-Log "===== Bootstrap FAILED ====="
-    Write-Log "ERROR: $($_.Exception.Message)"
-    Write-Log "Stack trace: $($_.ScriptStackTrace)"
-    Write-Log "Please check log file: $LogFile"
 
-    $errMsg = "AutopilotMonitor bootstrap failed: $($_.Exception.Message)"
-    if ($errMsg.Length -gt 2048) { $errMsg = $errMsg.Substring(0, 1045) + '...' }
-    [Console]::Error.WriteLine($errMsg)
-
-    exit 1
+# Entry guard: execute only when run as a script (IME, console). Dot-sourcing
+# (". .\Install-AutopilotMonitor-dev.ps1", as the Pester suite does) only loads
+# the functions above and MUST stay side-effect free.
+if ($MyInvocation.InvocationName -ne '.') {
+    Invoke-Bootstrap
 }

scripts/Bootstrap/Install-AutopilotMonitor.ps1

@@ -5,18 +5,28 @@
 .DESCRIPTION
     Designed to be deployed via Intune as a PowerShell Script during Autopilot.
     Runs very early in the enrollment process (first Intune action) and:
-      1. Runs five pre-flight guards to skip productive devices and ghost re-installs
+      1. Runs pre-flight guards to skip productive devices and ghost re-installs.
+         An OOBE-relax exemption allows install when a single freshly-created profile
+         appears DURING OOBE (the "Windows Backup for Organizations" restore case).
       2. Downloads the monitoring agent ZIP from Azure Blob Storage
-      3. Verifies integrity via SHA-256 hash from the version manifest
-         (legacy fallback: Content-MD5 header from the blob response)
+      3. Verifies integrity via SHA-256 hash from the version manifest (mandatory)
       4. Extracts the agent into %ProgramData%\AutopilotMonitor\Agent
       5. Runs the agent in --install mode (registers Scheduled Task, spawns the runtime)
       6. Verifies the runtime process actually launched
     Agent self-destructs when enrollment completes.
 
+    OOBE-relax flow (guards 2+3): a real user profile (or a real LastLoggedOnUser)
+    normally means "productive -> skip". Windows Backup for Organizations breaks that
+    by restoring settings and creating ONE profile while still in OOBE. We relax guards
+    2+3 ONLY when all three positives hold, and nothing else:
+      (a) the OS positively reports OOBE InProgress (Test-OobeInProgress), AND
+      (b) there is exactly ONE real user profile, AND
+      (c) that profile was created within $OobeProfileMaxAgeMinutes minutes.
+    Any miss keeps the original skip (SKIP-safe: we never install on uncertainty).
+
 .PARAMETER AgentDownloadUrl
-    URL to download the agent ZIP from. Defaults to the production blob; override only
-    for parallel lab/dev assignments that point at a separate pre-release ZIP.
+    URL to download the agent ZIP from. Defaults to the production download endpoint;
+    override only for parallel lab/dev assignments that point at a separate pre-release ZIP.
 
 .PARAMETER VersionJsonName
     Filename of the integrity manifest in the same blob container as the agent ZIP.
@@ -27,16 +37,35 @@
     valid. Devices booted more than this many hours ago are skipped because we no
     longer trust their OOBE state. Default: 12.
 
+.PARAMETER OobeProfileMaxAgeMinutes
+    Maximum age (minutes) of the single profile that may appear during OOBE for the
+    OOBE-relax exemption to apply. The restore->bootstrap gap is always minutes; an
+    older profile is treated as a productive device. Default: 15.
+
 .NOTES
     - Agent is temporary and auto-removes after enrollment.
     - All files live under C:\ProgramData\AutopilotMonitor (easy cleanup).
     - One registry key remains after removal: HKLM\SOFTWARE\AutopilotMonitor\Deployed
       (prevents ghost re-installs on re-Autopilot of the same device).
     - Scheduled Task survives reboots during enrollment.
+    - OOBE detection uses Windows.System.Profile.SystemSetupInfo.OutOfBoxExperienceState.
+      Requires Windows 10, version 1809 (introduced in 10.0.17763.0). Older builds lack
+      the class -> Test-OobeInProgress returns $false -> original (skip) behaviour. Docs:
+      https://learn.microsoft.com/en-us/uwp/api/windows.system.profile.systemsetupinfo
     - This script MUST remain pure ASCII (no Unicode/UTF-8 special chars).
       PowerShell 5.1 (IME) reads scripts without BOM as ANSI, corrupting multi-byte chars.
 
 .CHANGELOG
+    2026-07-20  v2.2  Switched default download endpoint from the legacy blob
+                      (autopilotmonitor.blob.core.windows.net) to the Front Door alias
+                      https://download.autopilotmonitor.com/agent/ (route /agent/*).
+                      version.json is still derived from the same container.
+    2026-06-25  v2.1  OOBE-relax: detect genuine OOBE via WinRT
+                      SystemSetupInfo.OutOfBoxExperienceState and exempt guards 2+3 when a
+                      single freshly-created profile appears in OOBE (Windows Backup for
+                      Organizations). SKIP-safe when the API is absent (< 1809).
+                      Removed legacy Content-MD5 fallback; SHA-256 manifest verification is
+                      now mandatory (no hash -> bootstrap aborts, no unverified install).
     2026-05-09  v2.0  Generic bootstrap: agent owns its own defaults (e.g. 600 s
                       TenantId-wait), so the script only calls `--install` plain.
                       Hardened post-install with a 10 s runtime-process verify.
@@ -55,17 +84,20 @@
 [CmdletBinding()]
 param(
     [Parameter(Mandatory = $false)]
-    [string]$AgentDownloadUrl = "https://autopilotmonitor.blob.core.windows.net/agent/AutopilotMonitor-Agent.zip",
+    [string]$AgentDownloadUrl = "https://download.autopilotmonitor.com/agent/AutopilotMonitor-Agent.zip",
 
     [Parameter(Mandatory = $false)]
     [string]$VersionJsonName = "version.json",
 
     [Parameter(Mandatory = $false)]
-    [int]$MaxBootstrapWindowHours = 12
+    [int]$MaxBootstrapWindowHours = 12,
+
+    [Parameter(Mandatory = $false)]
+    [int]$OobeProfileMaxAgeMinutes = 15
 )
 
 # Script version (bump on meaningful changes; see .CHANGELOG above)
-$ScriptVersion = "2.0"
+$ScriptVersion = "2.2"
 
 # Configuration - Everything in ProgramData for easy cleanup
 $AgentBasePath = "$env:ProgramData\AutopilotMonitor"
@@ -85,26 +117,19 @@ function Write-Log {
     Add-Content -Path $LogFile -Value $logMessage -ErrorAction SilentlyContinue
 }
 
-function Get-FileMd5Base64 {
-    param(
-        [Parameter(Mandatory = $true)]
-        [string]$Path
-    )
-
-    $md5 = [System.Security.Cryptography.MD5]::Create()
+# Positive OOBE check via the documented WinRT API
+# Windows.System.Profile.SystemSetupInfo.OutOfBoxExperienceState.
+# Returns $true ONLY when the OS reports InProgress. Any other state (Completed/NotStarted),
+# an older OS without the class (< Win10 1809 / 10.0.17763.0), or any error returns $false
+# -> SKIP-safe (we never relax a guard on uncertainty).
+# Docs: https://learn.microsoft.com/en-us/uwp/api/windows.system.profile.systemsetupinfo
+function Test-OobeInProgress {
     try {
-        $stream = [System.IO.File]::OpenRead($Path)
-        try {
-            $hashBytes = $md5.ComputeHash($stream)
-        }
-        finally {
-            $stream.Dispose()
-        }
-
-        return [Convert]::ToBase64String($hashBytes)
+        $null = [Windows.System.Profile.SystemSetupInfo, Windows.System.Profile, ContentType = WindowsRuntime]
+        return ([Windows.System.Profile.SystemSetupInfo]::OutOfBoxExperienceState).ToString() -eq 'InProgress'
     }
-    finally {
-        $md5.Dispose()
+    catch {
+        return $false
     }
 }
 
@@ -119,30 +144,65 @@ try {
         exit 0
     }
 
-    # Guard 2: No real user profile should exist yet (primary productive-device guard).
-    # Combines WMI (Win32_UserProfile.Special flag) and filesystem for maximum reliability.
-    $excludePattern = '^(defaultuser\d*|Public|Default( User)?|All Users)$'
+    # Collect real (non-special) user profiles as full paths (WMI Special flag + filesystem).
+    $excludePattern = '^(defaultuser\d*|Public|Default( User)?|All Users|WDAGUtilityAccount)$'
 
-    $profileNames = @(
+    # NOTE: the outer @() is required. Without it the trailing Where/Select pipeline
+    # unwraps a single result back to a scalar string, so $profilePaths[0] would index
+    # into the string and return its first char ('C') instead of the full path.
+    $profilePaths = @(
+        @(
+            try {
+                Get-CimInstance Win32_UserProfile -ErrorAction Stop |
+                    Where-Object { -not $_.Special -and $_.LocalPath -like 'C:\Users\*' } |
+                    ForEach-Object { $_.LocalPath }
+            } catch { Write-Log "INFO: WMI profile query failed, continuing with filesystem check." }
+
+            (Get-ChildItem 'C:\Users' -Directory -ErrorAction SilentlyContinue).FullName
+        ) | Where-Object { $_ -and (Split-Path $_ -Leaf) -notmatch $excludePattern } |
+            Select-Object -Unique
+    )
+
+    # OOBE-relax: the ONLY exemption to guards 2+3. Matches exactly the Windows Backup for
+    # Organizations restore (one user signs in + restores DURING OOBE). All three must hold:
+    #   OOBE InProgress  AND  exactly one profile  AND  that profile created < N minutes ago.
+    $oobeRelax = $false
+    $oobeInProgress = Test-OobeInProgress
+    if ($profilePaths.Count -eq 1 -and $oobeInProgress) {
         try {
-            Get-CimInstance Win32_UserProfile -ErrorAction Stop |
-                Where-Object { -not $_.Special -and $_.LocalPath -like 'C:\Users\*' } |
-                ForEach-Object { Split-Path $_.LocalPath -Leaf }
-        } catch { Write-Log "INFO: WMI profile query failed, continuing with filesystem check." }
+            $created = (Get-Item -LiteralPath $profilePaths[0] -Force -ErrorAction Stop).CreationTimeUtc
+            $ageMin = ((Get-Date).ToUniversalTime() - $created).TotalMinutes
+            if ($ageMin -ge 0 -and $ageMin -lt $OobeProfileMaxAgeMinutes) {
+                $oobeRelax = $true
+                Write-Log ("OOBE-relax active: OOBE InProgress + single profile created {0:N1}min ago (< {1}min). Guards 2+3 relaxed (Windows Backup restore case)." -f $ageMin, $OobeProfileMaxAgeMinutes)
+            } else {
+                Write-Log ("OOBE-relax NOT applied: OOBE InProgress + single profile '{0}', but profile created {1:N1}min ago (created {2:u}) is outside the [0, {3})min window." -f (Split-Path $profilePaths[0] -Leaf), $ageMin, $created, $OobeProfileMaxAgeMinutes)
+            }
+        } catch { Write-Log "INFO: profile age check failed; OOBE-relax not applied. $($_.Exception.Message)" }
+    } elseif ($profilePaths.Count -eq 1 -and -not $oobeInProgress) {
+        Write-Log "OOBE-relax NOT applied: single profile present but OutOfBoxExperienceState != InProgress (OOBE already finished / not detectable)."
+    } elseif ($profilePaths.Count -gt 1) {
+        Write-Log ("OOBE-relax NOT applied: {0} real profiles present (relax requires exactly one)." -f $profilePaths.Count)
+    }
 
-        (Get-ChildItem 'C:\Users' -Directory -ErrorAction SilentlyContinue).Name
-    ) | Where-Object { $_ -and $_ -notmatch $excludePattern } |
-        Select-Object -Unique
-
-    if ($profileNames) {
-        $names = ($profileNames | Select-Object -First 3) -join ', '
-        Write-Log "SKIP: Real user profile(s) found ($names). Device appears productive."
+    # Guard 2: No real user profile should exist yet (primary productive-device guard),
+    # unless the OOBE-relax signature holds.
+    if ($profilePaths.Count -gt 0 -and -not $oobeRelax) {
+        $details = (($profilePaths | ForEach-Object {
+            $leaf = Split-Path $_ -Leaf
+            try {
+                $c = (Get-Item -LiteralPath $_ -Force -ErrorAction Stop).CreationTimeUtc
+                "{0} (created {1:u}, {2:N1}min ago)" -f $leaf, $c, ((Get-Date).ToUniversalTime() - $c).TotalMinutes
+            } catch { "$leaf (age unknown)" }
+        }) | Select-Object -First 3) -join '; '
+        Write-Log "SKIP: Real user profile(s) found ($details). OOBE InProgress=$oobeInProgress. Device appears productive."
         exit 0
     }
 
-    # Guard 3: LastLoggedOnUser - during Device ESP no real user has logged on yet.
+    # Guard 3: LastLoggedOnUser - during Device ESP no real user has logged on yet
+    # (same OOBE-relax exemption: the restoring user signs in during OOBE).
     $lastLoggedOnUser = (Get-ItemProperty -Path 'HKLM:\SOFTWARE\Microsoft\Windows\CurrentVersion\Authentication\LogonUI' -Name 'LastLoggedOnUser' -EA SilentlyContinue).LastLoggedOnUser
-    if ($lastLoggedOnUser -and $lastLoggedOnUser -notmatch 'defaultuser\d*') {
+    if ($lastLoggedOnUser -and $lastLoggedOnUser -notmatch 'defaultuser\d*' -and -not $oobeRelax) {
         Write-Log "SKIP: LastLoggedOnUser found ($lastLoggedOnUser). Device appears productive."
         exit 0
     }
@@ -166,7 +226,7 @@ try {
         }
     }
 
-    Write-Log "Pre-flight checks passed -- no prior deployment, no real user profiles, no logged-on user, within bootstrap window"
+    Write-Log "Pre-flight checks passed -- no prior deployment, no productive-device signals, within bootstrap window (oobeRelax=$oobeRelax)"
 
     # Download and extract agent binaries
     $agentExePath = Join-Path $AgentBinPath "AutopilotMonitor.Agent.exe"
@@ -181,38 +241,47 @@ try {
             # Derive manifest URL from the agent download URL (same blob container)
             $versionJsonUrl = $AgentDownloadUrl -replace '[^/]+$', $VersionJsonName
             $expectedSha256 = $null
+            $manifestAttempts = 3
+            $manifestDelays = @(1, 2)   # short backoff between attempts; do not block enrollment
 
-            try {
-                Write-Log "Fetching $VersionJsonName from $versionJsonUrl for integrity verification..."
-                $versionJsonResponse = Invoke-RestMethod -Uri $versionJsonUrl -UseBasicParsing -TimeoutSec 5 -ErrorAction Stop
-                if ($versionJsonResponse.sha256) {
-                    $expectedSha256 = $versionJsonResponse.sha256.ToLowerInvariant()
-                    Write-Log "SHA-256 hash from manifest: $expectedSha256 (version: $($versionJsonResponse.version))"
-                } else {
-                    Write-Log "Manifest has no sha256 field - falling back to legacy MD5 check (older build)"
+            for ($attempt = 1; $attempt -le $manifestAttempts; $attempt++) {
+                try {
+                    Write-Log "Fetching $VersionJsonName (attempt ${attempt}/${manifestAttempts}) from $versionJsonUrl for integrity verification..."
+                    $versionJsonResponse = Invoke-RestMethod -Uri $versionJsonUrl -UseBasicParsing -TimeoutSec 5 -ErrorAction Stop
+                    if ($versionJsonResponse.sha256) {
+                        $expectedSha256 = $versionJsonResponse.sha256.ToLowerInvariant()
+                        Write-Log "SHA-256 hash from manifest: $expectedSha256 (version: $($versionJsonResponse.version))"
+                    } else {
+                        Write-Log "WARNING: Manifest has no sha256 field - integrity cannot be verified."
+                    }
+                    break   # manifest reached (with or without hash); retrying would not help
+                }
+                catch {
+                    Write-Log "WARNING: Could not fetch integrity manifest (attempt $attempt): $($_.Exception.Message)"
+                    if ($attempt -lt $manifestAttempts) {
+                        Start-Sleep -Seconds $manifestDelays[$attempt - 1]
+                    }
                 }
-            }
-            catch {
-                Write-Log "WARNING: Could not fetch manifest - falling back to legacy MD5 check: $($_.Exception.Message)"
             }
 
             $zipPath = Join-Path $env:TEMP "AutopilotMonitor-Agent.zip"
             $maxDownloadAttempts = 3
             $downloadAttempt = 0
-            $downloadResponse = $null
 
             do {
                 $downloadAttempt++
                 try {
                     Write-Log "Download attempt ${downloadAttempt}/${maxDownloadAttempts}"
-                    $downloadResponse = Invoke-WebRequest `
+                    $downloadStopwatch = [System.Diagnostics.Stopwatch]::StartNew()
+                    Invoke-WebRequest `
                         -Uri $AgentDownloadUrl `
                         -OutFile $zipPath `
                         -UseBasicParsing `
                         -TimeoutSec 30 `
-                        -ErrorAction Stop `
-                        -PassThru
-                    Write-Log "Downloaded agent to $zipPath"
+                        -ErrorAction Stop
+                    $downloadStopwatch.Stop()
+                    $downloadSeconds = [math]::Round($downloadStopwatch.Elapsed.TotalSeconds, 1)
+                    Write-Log "Downloaded agent to $zipPath (took ${downloadSeconds}s)"
                     break
                 }
                 catch {
@@ -227,29 +296,17 @@ try {
                 }
             } while ($downloadAttempt -lt $maxDownloadAttempts)
 
-            if ($expectedSha256) {
-                $actualSha256 = (Get-FileHash $zipPath -Algorithm SHA256).Hash.ToLowerInvariant()
-                Write-Log "Validating SHA-256 hash against manifest"
-                if ($actualSha256 -ne $expectedSha256) {
-                    throw "SHA-256 integrity check FAILED. Expected='$expectedSha256', Actual='$actualSha256'. Download may be tampered or corrupted."
-                }
-                Write-Log "SHA-256 integrity check passed"
+            # SHA-256 from the version manifest is the only accepted integrity proof.
+            # No hash -> refuse to install an unverified ZIP (SKIP-safe security posture).
+            if (-not $expectedSha256) {
+                throw "No SHA-256 hash available from manifest - refusing to install unverified agent ZIP."
             }
-            else {
-                $expectedMd5Header = $downloadResponse.Headers["Content-MD5"]
-                $expectedMd5 = if ($expectedMd5Header -is [System.Array]) { "$($expectedMd5Header[0])".Trim() } else { "$expectedMd5Header".Trim() }
-                if ($expectedMd5 -notmatch '\S') {
-                    Write-Log "WARNING: No SHA-256 and no Content-MD5 header - skipping integrity validation"
-                }
-                else {
-                    $actualMd5 = Get-FileMd5Base64 -Path $zipPath
-                    Write-Log "Validating Content-MD5 header against downloaded ZIP"
-                    if ($actualMd5 -ne $expectedMd5) {
-                        throw "MD5 integrity check failed. Expected (Content-MD5)='$expectedMd5', Actual='$actualMd5'"
-                    }
-                    Write-Log "MD5 integrity check passed"
-                }
+            $actualSha256 = (Get-FileHash $zipPath -Algorithm SHA256).Hash.ToLowerInvariant()
+            Write-Log "Validating SHA-256 hash against manifest"
+            if ($actualSha256 -ne $expectedSha256) {
+                throw "SHA-256 integrity check FAILED. Expected='$expectedSha256', Actual='$actualSha256'. Download may be tampered or corrupted."
             }
+            Write-Log "SHA-256 integrity check passed"
 
             Expand-Archive -Path $zipPath -DestinationPath $AgentBinPath -Force
             Write-Log "Extracted agent to $AgentBinPath"

scripts/Bootstrap/Test-ShouldBootstrapAgent-dev.ps1

@@ -1,213 +0,0 @@
-# Autopilot Monitor Bootstrap Guard Test (DEV)
-# Dry-run only: does not exit, does not install, only reports what WOULD happen.
-# Mirrors Install-AutopilotMonitor-dev.ps1 incl. the OOBE-relax exemption for the
-# "Windows Backup for Organizations" restore case (guards 2+3).
-
-param(
-    [string]$AgentBinPath = 'C:\ProgramData\AutopilotMonitor\Agent',
-    [int]$OobeProfileMaxAgeMinutes = 15
-)
-
-$ErrorActionPreference = 'SilentlyContinue'
-
-function Write-Step {
-    param(
-        [string]$Status,
-        [string]$Message
-    )
-
-    $prefix = switch ($Status) {
-        'PASS' { '[PASS]' }
-        'SKIP' { '[SKIP]' }
-        'WARN' { '[WARN]' }
-        'INFO' { '[INFO]' }
-        default { '[....]' }
-    }
-
-    Write-Host "$prefix $Message"
-}
-
-function Get-RegistryValueSafe {
-    param(
-        [string]$Path,
-        [string]$Name
-    )
-
-    try {
-        return (Get-ItemProperty -Path $Path -Name $Name -ErrorAction Stop).$Name
-    }
-    catch {
-        return $null
-    }
-}
-
-# Positive OOBE check via WinRT Windows.System.Profile.SystemSetupInfo.OutOfBoxExperienceState.
-# Requires Windows 10, version 1809 (10.0.17763.0). Older builds / errors -> $false (SKIP-safe).
-# Docs: https://learn.microsoft.com/en-us/uwp/api/windows.system.profile.systemsetupinfo
-function Test-OobeInProgress {
-    try {
-        $null = [Windows.System.Profile.SystemSetupInfo, Windows.System.Profile, ContentType = WindowsRuntime]
-        return ([Windows.System.Profile.SystemSetupInfo]::OutOfBoxExperienceState).ToString() -eq 'InProgress'
-    }
-    catch {
-        return $false
-    }
-}
-
-$AgentExePath = Join-Path $AgentBinPath 'AutopilotMonitor.Agent.exe'
-$MaxBootstrapWindowHours = 12
-
-$wouldInstall = $true
-$reasons = New-Object System.Collections.Generic.List[string]
-
-Write-Host ''
-Write-Host '=== Autopilot Monitor Bootstrap Guard Test (Dry Run, DEV) ==='
-Write-Host ''
-
-# Guard 1: Agent was already deployed on this device (survives self-destruct)
-$deployed = Get-RegistryValueSafe -Path 'HKLM:\SOFTWARE\AutopilotMonitor' -Name 'Deployed'
-if ($deployed) {
-    Write-Step -Status 'SKIP' -Message "Guard 1: Agent was previously deployed at '$deployed'."
-    $wouldInstall = $false
-    $reasons.Add("Previously deployed marker exists: $deployed")
-} else {
-    Write-Step -Status 'PASS' -Message 'Guard 1: No previous deployment marker found.'
-}
-
-# Collect real (non-special) user profiles as full paths (combined WMI/filesystem view).
-$excludePattern = '^(defaultuser\d*|Public|Default( User)?|All Users|WDAGUtilityAccount)$'
-$wmiProfileQueryFailed = $false
-
-# NOTE: the outer @() is required. Without it the trailing Where/Select pipeline
-# unwraps a single result back to a scalar string, so $profilePaths[0] would index
-# into the string and return its first char ('C') instead of the full path.
-$profilePaths = @(
-    @(
-        try {
-            Get-CimInstance Win32_UserProfile -ErrorAction Stop |
-                Where-Object { -not $_.Special -and $_.LocalPath -like 'C:\Users\*' } |
-                ForEach-Object { $_.LocalPath }
-        }
-        catch {
-            $wmiProfileQueryFailed = $true
-        }
-
-        (Get-ChildItem 'C:\Users' -Directory -ErrorAction SilentlyContinue).FullName
-    ) |
-    Where-Object { $_ -and (Split-Path $_ -Leaf) -notmatch $excludePattern } |
-    Select-Object -Unique
-)
-
-if ($wmiProfileQueryFailed) {
-    Write-Step -Status 'WARN' -Message 'Profiles: WMI query failed, filesystem check still applied.'
-}
-
-$profileNames = $profilePaths | ForEach-Object { Split-Path $_ -Leaf }
-
-# OOBE-relax: the ONLY exemption to guards 2+3. Matches exactly the Windows Backup for
-# Organizations restore: OOBE InProgress AND exactly one profile AND that profile fresh.
-$oobeInProgress = Test-OobeInProgress
-$profileAgeMin = $null
-$oobeRelax = $false
-if ($profilePaths.Count -eq 1) {
-    try {
-        $created = (Get-Item -LiteralPath $profilePaths[0] -Force -ErrorAction Stop).CreationTimeUtc
-        $profileAgeMin = [math]::Round(((Get-Date).ToUniversalTime() - $created).TotalMinutes, 1)
-    } catch { }
-    if ($oobeInProgress -and $null -ne $profileAgeMin -and $profileAgeMin -ge 0 -and $profileAgeMin -lt $OobeProfileMaxAgeMinutes) {
-        $oobeRelax = $true
-    }
-}
-
-Write-Step -Status 'INFO' -Message "OOBE: OutOfBoxExperienceState InProgress = $oobeInProgress ; profileCount = $($profilePaths.Count) ; singleProfileAgeMin = $profileAgeMin ; OOBE-relax = $oobeRelax"
-
-# Guard 2: No real user profile should exist yet (unless OOBE-relax holds)
-if ($profilePaths.Count -gt 0 -and -not $oobeRelax) {
-    $names = ($profileNames | Select-Object -First 3) -join ', '
-    Write-Step -Status 'SKIP' -Message "Guard 2: Real user profile(s) found ($names). Device appears productive."
-    $wouldInstall = $false
-    $reasons.Add("Real user profile(s) found: $names")
-} elseif ($profilePaths.Count -gt 0 -and $oobeRelax) {
-    $names = ($profileNames | Select-Object -First 3) -join ', '
-    Write-Step -Status 'PASS' -Message "Guard 2: Profile ($names) present but OOBE-relax active (single fresh profile in OOBE) -- not blocking."
-} else {
-    Write-Step -Status 'PASS' -Message 'Guard 2: No real user profiles found (combined WMI/filesystem view).'
-}
-
-# Guard 3: LastLoggedOnUser (unless OOBE-relax holds)
-$lastLoggedOnUser = (Get-ItemProperty -Path 'HKLM:\SOFTWARE\Microsoft\Windows\CurrentVersion\Authentication\LogonUI' -Name 'LastLoggedOnUser' -EA SilentlyContinue).LastLoggedOnUser
-if ($lastLoggedOnUser -and $lastLoggedOnUser -notmatch 'defaultuser\d*' -and -not $oobeRelax) {
-    Write-Step -Status 'SKIP' -Message "Guard 3: LastLoggedOnUser found ($lastLoggedOnUser). Device appears productive."
-    $wouldInstall = $false
-    $reasons.Add("LastLoggedOnUser found: $lastLoggedOnUser")
-} elseif ($lastLoggedOnUser -and $lastLoggedOnUser -notmatch 'defaultuser\d*' -and $oobeRelax) {
-    Write-Step -Status 'PASS' -Message "Guard 3: LastLoggedOnUser ($lastLoggedOnUser) present but OOBE-relax active -- not blocking."
-} else {
-    Write-Step -Status 'PASS' -Message "Guard 3: No real LastLoggedOnUser (value: '$lastLoggedOnUser')."
-}
-
-# Guard 4: Bootstrap window check (sleep/standby does NOT reset uptime, only real boot does)
-$lastBoot = $null
-$uptimeHours = $null
-
-try {
-    $lastBoot = (Get-CimInstance Win32_OperatingSystem -ErrorAction Stop).LastBootUpTime
-    $uptimeHours = ((Get-Date) - $lastBoot).TotalHours
-
-    if ($uptimeHours -gt $MaxBootstrapWindowHours) {
-        Write-Step -Status 'SKIP' -Message "Guard 4: Device uptime is $([int]$uptimeHours)h. Older than accepted bootstrap window of ${MaxBootstrapWindowHours}h."
-        $wouldInstall = $false
-        $reasons.Add("Uptime exceeds bootstrap window: $([int]$uptimeHours)h > ${MaxBootstrapWindowHours}h")
-    } else {
-        Write-Step -Status 'PASS' -Message "Guard 4: Device uptime is $([int]$uptimeHours)h and within bootstrap window of ${MaxBootstrapWindowHours}h."
-    }
-}
-catch {
-    Write-Step -Status 'WARN' -Message 'Guard 4: Could not determine LastBootUpTime / uptime.'
-}
-
-# Guard 5: Agent binary already present
-if (Test-Path $AgentExePath) {
-    Write-Step -Status 'SKIP' -Message "Guard 5: Agent already installed at '$AgentExePath'."
-    $wouldInstall = $false
-    $reasons.Add("Agent binary already present: $AgentExePath")
-} else {
-    Write-Step -Status 'PASS' -Message "Guard 5: Agent binary not present at '$AgentExePath'."
-}
-
-Write-Host ''
-Write-Host '=== Result ==='
-Write-Host ''
-
-if ($wouldInstall) {
-    Write-Host '[DECISION] WOULD INSTALL agent on this device.'
-} else {
-    Write-Host '[DECISION] WOULD SKIP agent installation on this device.'
-}
-
-Write-Host ''
-Write-Host '=== Summary ==='
-
-if ($reasons.Count -eq 0) {
-    Write-Host 'No blocking reasons found.'
-} else {
-    foreach ($reason in $reasons) {
-        Write-Host " - $reason"
-    }
-}
-
-Write-Host ''
-Write-Host '=== Raw Values ==='
-Write-Host "Deployed marker           : $deployed"
-Write-Host "DetectedProfileNames      : $($profileNames -join ', ')"
-Write-Host "ProfileCount              : $($profilePaths.Count)"
-Write-Host "OobeInProgress (WinRT)    : $oobeInProgress"
-Write-Host "SingleProfileAgeMinutes   : $profileAgeMin"
-Write-Host "OobeProfileMaxAgeMinutes  : $OobeProfileMaxAgeMinutes"
-Write-Host "OobeRelaxActive           : $oobeRelax"
-Write-Host "LastLoggedOnUser          : $lastLoggedOnUser"
-Write-Host "MaxBootstrapWindowHours   : $MaxBootstrapWindowHours"
-Write-Host "LastBootUpTime            : $lastBoot"
-Write-Host "UptimeHours               : $([string]$uptimeHours)"
-Write-Host "AgentExePath              : $AgentExePath"
-Write-Host ''

scripts/Bootstrap/Test-ShouldBootstrapAgent.ps1

@@ -1,8 +1,11 @@
 # Autopilot Monitor Bootstrap Guard Test
 # Dry-run only: does not exit, does not install, only reports what WOULD happen.
+# Mirrors Install-AutopilotMonitor.ps1 incl. the OOBE-relax exemption for the
+# "Windows Backup for Organizations" restore case (guards 2+3).
 
 param(
-    [string]$AgentBinPath = 'C:\ProgramData\AutopilotMonitor\Agent'
+    [string]$AgentBinPath = 'C:\ProgramData\AutopilotMonitor\Agent',
+    [int]$OobeProfileMaxAgeMinutes = 15
 )
 
 $ErrorActionPreference = 'SilentlyContinue'
@@ -38,6 +41,19 @@ function Get-RegistryValueSafe {
     }
 }
 
+# Positive OOBE check via WinRT Windows.System.Profile.SystemSetupInfo.OutOfBoxExperienceState.
+# Requires Windows 10, version 1809 (10.0.17763.0). Older builds / errors -> $false (SKIP-safe).
+# Docs: https://learn.microsoft.com/en-us/uwp/api/windows.system.profile.systemsetupinfo
+function Test-OobeInProgress {
+    try {
+        $null = [Windows.System.Profile.SystemSetupInfo, Windows.System.Profile, ContentType = WindowsRuntime]
+        return ([Windows.System.Profile.SystemSetupInfo]::OutOfBoxExperienceState).ToString() -eq 'InProgress'
+    }
+    catch {
+        return $false
+    }
+}
+
 $AgentExePath = Join-Path $AgentBinPath 'AutopilotMonitor.Agent.exe'
 $MaxBootstrapWindowHours = 12
 
@@ -58,63 +74,79 @@ if ($deployed) {
     Write-Step -Status 'PASS' -Message 'Guard 1: No previous deployment marker found.'
 }
 
-# Guard 2: No real user profile should exist yet (primary productive-device guard)
-# NOTE: OOBEInProgress is NOT used -- it is unreliable (observed =0 during active enrollment).
-$excludePattern = '^(defaultuser\d*|Public|Default( User)?|All Users)$'
+# Collect real (non-special) user profiles as full paths (combined WMI/filesystem view).
+$excludePattern = '^(defaultuser\d*|Public|Default( User)?|All Users|WDAGUtilityAccount)$'
 $wmiProfileQueryFailed = $false
 
-$profileNames = @(
-    # WMI/CIM view -- Special flag reliably excludes SYSTEM/LocalService/NetworkService
-    try {
-        Get-CimInstance Win32_UserProfile -ErrorAction Stop |
-            Where-Object {
-                -not $_.Special -and
-                $_.LocalPath -like 'C:\Users\*'
-            } |
-            ForEach-Object {
-                Split-Path $_.LocalPath -Leaf
-            }
-    }
-    catch {
-        $wmiProfileQueryFailed = $true
-    }
+# NOTE: the outer @() is required. Without it the trailing Where/Select pipeline
+# unwraps a single result back to a scalar string, so $profilePaths[0] would index
+# into the string and return its first char ('C') instead of the full path.
+$profilePaths = @(
+    @(
+        try {
+            Get-CimInstance Win32_UserProfile -ErrorAction Stop |
+                Where-Object { -not $_.Special -and $_.LocalPath -like 'C:\Users\*' } |
+                ForEach-Object { $_.LocalPath }
+        }
+        catch {
+            $wmiProfileQueryFailed = $true
+        }
 
-    # Filesystem view -- catches profiles WMI might miss
-    (Get-ChildItem 'C:\Users' -Directory -ErrorAction SilentlyContinue).Name
-) |
-Where-Object {
-    $_ -and $_ -notmatch $excludePattern
-} |
-Select-Object -Unique
+        (Get-ChildItem 'C:\Users' -Directory -ErrorAction SilentlyContinue).FullName
+    ) |
+    Where-Object { $_ -and (Split-Path $_ -Leaf) -notmatch $excludePattern } |
+    Select-Object -Unique
+)
 
 if ($wmiProfileQueryFailed) {
-    Write-Step -Status 'WARN' -Message 'Guard 2: WMI profile query failed, filesystem check still applied.'
+    Write-Step -Status 'WARN' -Message 'Profiles: WMI query failed, filesystem check still applied.'
 }
 
-if ($profileNames) {
+$profileNames = $profilePaths | ForEach-Object { Split-Path $_ -Leaf }
+
+# OOBE-relax: the ONLY exemption to guards 2+3. Matches exactly the Windows Backup for
+# Organizations restore: OOBE InProgress AND exactly one profile AND that profile fresh.
+$oobeInProgress = Test-OobeInProgress
+$profileAgeMin = $null
+$oobeRelax = $false
+if ($profilePaths.Count -eq 1) {
+    try {
+        $created = (Get-Item -LiteralPath $profilePaths[0] -Force -ErrorAction Stop).CreationTimeUtc
+        $profileAgeMin = [math]::Round(((Get-Date).ToUniversalTime() - $created).TotalMinutes, 1)
+    } catch { }
+    if ($oobeInProgress -and $null -ne $profileAgeMin -and $profileAgeMin -ge 0 -and $profileAgeMin -lt $OobeProfileMaxAgeMinutes) {
+        $oobeRelax = $true
+    }
+}
+
+Write-Step -Status 'INFO' -Message "OOBE: OutOfBoxExperienceState InProgress = $oobeInProgress ; profileCount = $($profilePaths.Count) ; singleProfileAgeMin = $profileAgeMin ; OOBE-relax = $oobeRelax"
+
+# Guard 2: No real user profile should exist yet (unless OOBE-relax holds)
+if ($profilePaths.Count -gt 0 -and -not $oobeRelax) {
     $names = ($profileNames | Select-Object -First 3) -join ', '
     Write-Step -Status 'SKIP' -Message "Guard 2: Real user profile(s) found ($names). Device appears productive."
     $wouldInstall = $false
     $reasons.Add("Real user profile(s) found: $names")
+} elseif ($profilePaths.Count -gt 0 -and $oobeRelax) {
+    $names = ($profileNames | Select-Object -First 3) -join ', '
+    Write-Step -Status 'PASS' -Message "Guard 2: Profile ($names) present but OOBE-relax active (single fresh profile in OOBE) -- not blocking."
 } else {
     Write-Step -Status 'PASS' -Message 'Guard 2: No real user profiles found (combined WMI/filesystem view).'
 }
 
-# Guard 3: LastLoggedOnUser -- during Device ESP no real user has logged on yet
+# Guard 3: LastLoggedOnUser (unless OOBE-relax holds)
 $lastLoggedOnUser = (Get-ItemProperty -Path 'HKLM:\SOFTWARE\Microsoft\Windows\CurrentVersion\Authentication\LogonUI' -Name 'LastLoggedOnUser' -EA SilentlyContinue).LastLoggedOnUser
-if ($lastLoggedOnUser -and $lastLoggedOnUser -notmatch 'defaultuser\d*') {
+if ($lastLoggedOnUser -and $lastLoggedOnUser -notmatch 'defaultuser\d*' -and -not $oobeRelax) {
     Write-Step -Status 'SKIP' -Message "Guard 3: LastLoggedOnUser found ($lastLoggedOnUser). Device appears productive."
     $wouldInstall = $false
     $reasons.Add("LastLoggedOnUser found: $lastLoggedOnUser")
+} elseif ($lastLoggedOnUser -and $lastLoggedOnUser -notmatch 'defaultuser\d*' -and $oobeRelax) {
+    Write-Step -Status 'PASS' -Message "Guard 3: LastLoggedOnUser ($lastLoggedOnUser) present but OOBE-relax active -- not blocking."
 } else {
     Write-Step -Status 'PASS' -Message "Guard 3: No real LastLoggedOnUser (value: '$lastLoggedOnUser')."
 }
 
-# Guard 4: Bootstrap window check
-# NOT "how long may enrollment take" -- agent handles that internally (6h emergency break).
-# This is "how old can the OOBE state be before I no longer trust it for initial install".
-# 12h bootstrap window vs 6h agent emergency break = consistent layered approach.
-# Sleep/standby does NOT reset uptime -- only real boot/restart does.
+# Guard 4: Bootstrap window check (sleep/standby does NOT reset uptime, only real boot does)
 $lastBoot = $null
 $uptimeHours = $null
 
@@ -134,7 +166,7 @@ catch {
     Write-Step -Status 'WARN' -Message 'Guard 4: Could not determine LastBootUpTime / uptime.'
 }
 
-# Guard 4: Agent binary already present
+# Guard 5: Agent binary already present
 if (Test-Path $AgentExePath) {
     Write-Step -Status 'SKIP' -Message "Guard 5: Agent already installed at '$AgentExePath'."
     $wouldInstall = $false
@@ -168,6 +200,11 @@ Write-Host ''
 Write-Host '=== Raw Values ==='
 Write-Host "Deployed marker           : $deployed"
 Write-Host "DetectedProfileNames      : $($profileNames -join ', ')"
+Write-Host "ProfileCount              : $($profilePaths.Count)"
+Write-Host "OobeInProgress (WinRT)    : $oobeInProgress"
+Write-Host "SingleProfileAgeMinutes   : $profileAgeMin"
+Write-Host "OobeProfileMaxAgeMinutes  : $OobeProfileMaxAgeMinutes"
+Write-Host "OobeRelaxActive           : $oobeRelax"
 Write-Host "LastLoggedOnUser          : $lastLoggedOnUser"
 Write-Host "MaxBootstrapWindowHours   : $MaxBootstrapWindowHours"
 Write-Host "LastBootUpTime            : $lastBoot"

scripts/CustomerSetup/Grant-AutopilotMonitorAddOn.ps1

@@ -23,7 +23,11 @@
     One or more high-level feature identifiers. The script translates each to the underlying
     Graph permissions. Use this when you don't want to know permission strings.
     Available features:
-      - ScriptDisplayNames -> DeviceManagementScripts.Read.All
+      - ScriptDisplayNames     -> DeviceManagementScripts.Read.All
+      - W365CloudPcValidation  -> CloudPC.Read.All
+        (validates Windows 365 Cloud PCs against the tenant's Cloud PC inventory --
+         Cloud PCs are never Autopilot-registered, so this enables agent monitoring
+         of Cloud PC first-connect enrollment)
 
 .PARAMETER Permissions
     Microsoft Graph application permission names to grant directly. Use when the admin UI
@@ -76,7 +80,7 @@ param(
     [string]$ClientId,
 
     [Parameter(Mandatory = $true, ParameterSetName = 'ByFeatures')]
-    [ValidateSet('ScriptDisplayNames')]
+    [ValidateSet('ScriptDisplayNames', 'W365CloudPcValidation')]
     [string[]]$Features,
 
     [Parameter(Mandatory = $true, ParameterSetName = 'ByPermissions')]
@@ -97,7 +101,8 @@ $ErrorActionPreference = 'Stop'
 # ---- Feature -> Graph permission catalog -----------------------------------
 # Keep in lock-step with src/Shared/AutopilotMonitor.Shared/Models/Graph/GraphFeatureCatalog.cs
 $FeatureCatalog = @{
-    'ScriptDisplayNames' = @('DeviceManagementScripts.Read.All')
+    'ScriptDisplayNames'    = @('DeviceManagementScripts.Read.All')
+    'W365CloudPcValidation' = @('CloudPC.Read.All')
 }
 
 # Translate Features -> Permissions when caller used the high-level form.

src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/Configuration/RemoteConfigMergerTests.cs

@@ -285,6 +285,54 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Configuration
             Assert.Equal(@"C:\Temp\custom-ime.log", agent.ImeMatchLogPath);
         }
 
+        [Fact]
+        public void Merge_maps_enable_gather_rule_debug_log_true_to_default_path()
+        {
+            var agent = NewAgentConfig();
+            agent.GatherRuleDebugLogPath = null;
+
+            var remote = FullRemote();
+            remote.EnableGatherRuleDebugLog = true;
+
+            RemoteConfigMerger.Merge(agent, remote);
+
+            Assert.False(string.IsNullOrEmpty(agent.GatherRuleDebugLogPath));
+            Assert.Equal(
+                Environment.ExpandEnvironmentVariables(Constants.GatherRuleDebugLogPath),
+                agent.GatherRuleDebugLogPath);
+        }
+
+        [Fact]
+        public void Merge_maps_enable_gather_rule_debug_log_false_clears_path()
+        {
+            var agent = NewAgentConfig();
+            agent.GatherRuleDebugLogPath = Environment.ExpandEnvironmentVariables(Constants.GatherRuleDebugLogPath);
+
+            var remote = FullRemote();
+            remote.EnableGatherRuleDebugLog = false;
+
+            RemoteConfigMerger.Merge(agent, remote);
+
+            Assert.Null(agent.GatherRuleDebugLogPath);
+        }
+
+        [Fact]
+        public void Merge_preserves_custom_gather_rule_debug_log_path_when_remote_disables()
+        {
+            // A dev-time --gather-debug-log <custom> override seeds a non-default path on the
+            // AgentConfiguration. When the tenant remote flips EnableGatherRuleDebugLog off we
+            // keep the custom path rather than clobbering a deliberate dev override.
+            var agent = NewAgentConfig();
+            agent.GatherRuleDebugLogPath = @"C:\Temp\custom-gather.log";
+
+            var remote = FullRemote();
+            remote.EnableGatherRuleDebugLog = false;
+
+            RemoteConfigMerger.Merge(agent, remote);
+
+            Assert.Equal(@"C:\Temp\custom-gather.log", agent.GatherRuleDebugLogPath);
+        }
+
         // ============================================================= Null / partial tolerance
 
         [Fact]

src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/Monitoring/Gather/GatherRuleDebugLogTests.cs

@@ -0,0 +1,104 @@
+using System;
+using System.IO;
+using System.Linq;
+using AutopilotMonitor.Agent.V2.Core.Logging;
+using AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.Ime;
+using AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather;
+using AutopilotMonitor.Agent.V2.Core.Tests.Harness;
+using Xunit;
+
+namespace AutopilotMonitor.Agent.V2.Core.Tests.Monitoring.Gather
+{
+    /// <summary>
+    /// Writer unit tests for <see cref="GatherRuleDebugLog"/>: line format, lazy directory
+    /// creation, size-cap rotation, and the null-writer no-op path on the context.
+    /// </summary>
+    public sealed class GatherRuleDebugLogTests : IDisposable
+    {
+        private readonly TempDirectory _tmp = new TempDirectory();
+        private readonly AgentLogger _logger;
+
+        public GatherRuleDebugLogTests()
+        {
+            _logger = new AgentLogger(_tmp.Path, AgentLogLevel.Info);
+        }
+
+        public void Dispose() => _tmp.Dispose();
+
+        private string LogPath => Path.Combine(_tmp.Path, "sub", "gather_rules_debug.log");
+
+        [Fact]
+        public void Write_produces_pipe_delimited_line_and_creates_directory_lazily()
+        {
+            var log = new GatherRuleDebugLog(LogPath, _logger);
+            Assert.False(File.Exists(LogPath)); // lazy — nothing until the first write
+
+            log.Write("RULE-1", GatherRuleDebugLog.StageScope, "skipped: out of scope");
+
+            var lines = File.ReadAllLines(LogPath);
+            Assert.Equal(2, lines.Length); // header + entry
+            Assert.Contains("| - | config | -- gather rule debug log started --", lines[0]);
+            var parts = lines[1].Split(new[] { " | " }, StringSplitOptions.None);
+            Assert.Equal(4, parts.Length);
+            Assert.Equal("RULE-1", parts[1]);
+            Assert.Equal("scope", parts[2]);
+            Assert.Equal("skipped: out of scope", parts[3]);
+        }
+
+        [Fact]
+        public void Write_flattens_newlines_except_for_error_stage()
+        {
+            var log = new GatherRuleDebugLog(LogPath, _logger);
+            log.Write("RULE-1", GatherRuleDebugLog.StageCollector, "line1\r\nline2");
+            log.Write("RULE-1", GatherRuleDebugLog.StageError, "boom\r\n   at Frame()");
+
+            var content = File.ReadAllText(LogPath);
+            Assert.Contains("line1 line2", content);
+            Assert.Contains("   at Frame()", content); // error stage keeps the stack multi-line
+        }
+
+        [Fact]
+        public void Write_null_ruleId_renders_dash()
+        {
+            var log = new GatherRuleDebugLog(LogPath, _logger);
+            log.Write(null, GatherRuleDebugLog.StageConfig, "no rules delivered");
+
+            Assert.Contains(" | - | config | no rules delivered", File.ReadAllText(LogPath));
+        }
+
+        [Fact]
+        public void Write_rotates_once_when_file_exceeds_cap()
+        {
+            var log = new GatherRuleDebugLog(LogPath, _logger, maxBytes: 512);
+            for (int i = 0; i < 20; i++)
+                log.Write("RULE-1", GatherRuleDebugLog.StageExec, new string('x', 100));
+
+            var oldPath = Path.Combine(Path.GetDirectoryName(LogPath), "gather_rules_debug.old.log");
+            Assert.True(File.Exists(oldPath), "expected one .old rotation generation");
+            Assert.True(File.Exists(LogPath));
+            Assert.Contains("-- rotated", File.ReadAllText(LogPath) + File.ReadAllText(oldPath));
+            // Never more than one .old generation
+            Assert.Single(Directory.GetFiles(Path.GetDirectoryName(LogPath), "*.old.log"));
+        }
+
+        [Fact]
+        public void WriteStandalone_writes_single_config_line()
+        {
+            GatherRuleDebugLog.WriteStandalone(LogPath, "no gather rules delivered by backend — nothing to execute", _logger);
+
+            var lines = File.ReadAllLines(LogPath);
+            Assert.Contains(lines, l => l.Contains("no gather rules delivered by backend"));
+        }
+
+        [Fact]
+        public void Context_DebugLog_is_noop_without_writer()
+        {
+            var context = new GatherRuleContext(
+                _logger, "sess", "tenant", _ => { }, null, new LogFilePositionTracker());
+
+            context.DebugLog("RULE-1", GatherRuleDebugLog.StageScope, "should not throw, should not write");
+
+            Assert.False(File.Exists(LogPath));
+        }
+    }
+}

src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/Monitoring/Gather/GatherRuleExecutorDebugLogTests.cs

@@ -0,0 +1,174 @@
+using System;
+using System.Collections.Generic;
+using System.IO;
+using AutopilotMonitor.Agent.V2.Core.Logging;
+using AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather;
+using AutopilotMonitor.Agent.V2.Core.Tests.Harness;
+using AutopilotMonitor.Shared.Models;
+using Xunit;
+
+namespace AutopilotMonitor.Agent.V2.Core.Tests.Monitoring.Gather
+{
+    /// <summary>
+    /// Debug-trace coverage of <see cref="GatherRuleExecutor"/> (EnableGatherRuleDebugLog):
+    /// every "silently produced nothing" outcome must leave an explanatory line in the trace
+    /// file — registration summary, missing interval, scope skips, on_change suppression,
+    /// empty collector results.
+    /// </summary>
+    [Collection("SerialThreading")] // startup rules execute on the shared ThreadPool
+    public sealed class GatherRuleExecutorDebugLogTests : IDisposable
+    {
+        private readonly TempDirectory _tmp = new TempDirectory();
+        private readonly GatherRuleExecutor _executor;
+        private readonly string _debugLogPath;
+
+        private const string AbsentPath =
+            "HKLM\\SOFTWARE\\AutopilotMonitorTests\\DefinitelyAbsent_7e3a1f4b-0000-0000-0000-000000000000";
+
+        public GatherRuleExecutorDebugLogTests()
+        {
+            var logger = new AgentLogger(_tmp.Path, AgentLogLevel.Info);
+            _debugLogPath = Path.Combine(_tmp.Path, "gather_rules_debug.log");
+            _executor = new GatherRuleExecutor(
+                "sess", "tenant", _ => { }, logger,
+                debugLogPath: _debugLogPath)
+            {
+                UnrestrictedMode = true
+            };
+        }
+
+        public void Dispose()
+        {
+            _executor.Dispose();
+            _tmp.Dispose();
+        }
+
+        private string TraceContent() => File.Exists(_debugLogPath) ? File.ReadAllText(_debugLogPath) : string.Empty;
+
+        private static GatherRule Rule(string id, Action<GatherRule>? mutate = null)
+        {
+            var rule = new GatherRule
+            {
+                RuleId = id,
+                Title = id,
+                CollectorType = "registry",
+                Target = AbsentPath,
+                Trigger = "startup",
+                OutputEventType = "gather_test",
+                Enabled = true,
+            };
+            mutate?.Invoke(rule);
+            return rule;
+        }
+
+        [Fact]
+        public void UpdateRules_writes_registration_summary_per_rule()
+        {
+            _executor.UpdateRules(new List<GatherRule>
+            {
+                Rule("GATHER-REG-001", r => { r.Trigger = "interval"; r.IntervalSeconds = 3600; r.EmitMode = "on_change"; }),
+                Rule("GATHER-REG-002", r => r.Enabled = false),
+            });
+            _executor.WaitForStartupRules(30);
+
+            var trace = TraceContent();
+            Assert.Contains("GATHER-REG-001 | config | registered: trigger=interval, collector=registry", trace);
+            Assert.Contains("emitMode=on_change", trace);
+            Assert.Contains("interval=3600s", trace);
+            Assert.Contains("GATHER-REG-002 | config | rule disabled — will never run", trace);
+            Assert.Contains("interval timer scheduled every 3600s (first run after one full interval", trace);
+        }
+
+        [Fact]
+        public void UpdateRules_flags_interval_rule_without_intervalSeconds()
+        {
+            _executor.UpdateRules(new List<GatherRule>
+            {
+                Rule("GATHER-NOINT-001", r => { r.Trigger = "interval"; r.IntervalSeconds = null; }),
+            });
+
+            Assert.Contains("GATHER-NOINT-001 | error | trigger=interval but intervalSeconds is missing — rule will NEVER run",
+                TraceContent());
+        }
+
+        [Fact]
+        public void ScopedRule_skip_traces_unknown_phase_reason()
+        {
+            var rule = Rule("GATHER-SCOPE-001", r => { r.Trigger = "interval"; r.IntervalSeconds = 3600; r.ActivePhases = new List<string> { "DeviceSetup" }; });
+            _executor.UpdateRules(new List<GatherRule> { rule });
+
+            // Synchronous internal check mirrors the timer-tick gate; the reason must name Unknown.
+            string reason;
+            Assert.False(_executor.IsRuleInScope(rule, out reason));
+            Assert.Contains("currentPhase=Unknown", reason);
+        }
+
+        [Fact]
+        public void ScopedStartupRule_deferral_is_traced()
+        {
+            _executor.UpdateRules(new List<GatherRule>
+            {
+                Rule("GATHER-DEFER-001", r => r.ActivePhases = new List<string> { "DeviceSetup" }),
+            });
+
+            Assert.Contains("GATHER-DEFER-001 | scope | startup rule deferred — currentPhase=Unknown", TraceContent());
+        }
+
+        [Fact]
+        public void OnChange_suppression_and_reemission_are_traced()
+        {
+            var rule = Rule("GATHER-OC-001", r => { r.Trigger = "interval"; r.IntervalSeconds = 3600; r.EmitMode = "on_change"; });
+            _executor.UpdateRules(new List<GatherRule> { rule });
+
+            string hashPrefix;
+            int streak;
+            var first = new Dictionary<string, object> { ["exists"] = false };
+            Assert.True(_executor.ShouldEmitOnChange(rule, first, out hashPrefix, out streak));
+            Assert.Equal(0, streak);
+            Assert.False(string.IsNullOrEmpty(hashPrefix));
+
+            Assert.False(_executor.ShouldEmitOnChange(rule, new Dictionary<string, object> { ["exists"] = false }, out hashPrefix, out streak));
+            Assert.Equal(1, streak);
+            Assert.False(_executor.ShouldEmitOnChange(rule, new Dictionary<string, object> { ["exists"] = false }, out hashPrefix, out streak));
+            Assert.Equal(2, streak);
+
+            var changed = new Dictionary<string, object> { ["exists"] = true };
+            Assert.True(_executor.ShouldEmitOnChange(rule, changed, out hashPrefix, out streak));
+            Assert.Equal(2, streak); // the streak that just ended
+            Assert.Equal(2, changed["suppressedPolls"]);
+        }
+
+        [Fact]
+        public void PhaseChange_writes_transition_line()
+        {
+            _executor.UpdateRules(new List<GatherRule> { Rule("GATHER-PHASE-001") });
+            _executor.WaitForStartupRules(30);
+
+            _executor.OnPhaseChanged(EnrollmentPhase.DeviceSetup);
+            _executor.OnPhaseChanged(EnrollmentPhase.AccountSetup);
+            _executor.OnPhaseChanged(EnrollmentPhase.AccountSetup); // repeat — no extra line
+
+            var trace = TraceContent();
+            Assert.Contains("- | phase | phase change: Unknown -> DeviceSetup (first phase signal", trace);
+            Assert.Contains("- | phase | phase change: DeviceSetup -> AccountSetup", trace);
+            // A repeated signal for the same phase must not produce a second transition line.
+            var marker = "phase change: DeviceSetup -> AccountSetup";
+            Assert.Equal(trace.IndexOf(marker), trace.LastIndexOf(marker));
+        }
+
+        [Fact]
+        public void EmptyCollectorResult_is_traced_via_startup_execution()
+        {
+            _executor.UpdateRules(new List<GatherRule>
+            {
+                Rule("GATHER-EMPTY-001", r => r.Parameters = new Dictionary<string, string> { ["emitOnlyIfExists"] = "true" }),
+            });
+            Assert.True(_executor.WaitForStartupRules(30));
+
+            var trace = TraceContent();
+            Assert.Contains("GATHER-EMPTY-001 | exec | executing: collector=registry", trace);
+            Assert.Contains("GATHER-EMPTY-001 | collector | registry key/value not found", trace);
+            Assert.Contains("GATHER-EMPTY-001 | collector | collector returned EMPTY result — nothing emitted", trace);
+        }
+    }
+}

src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/Monitoring/Gather/LogParserCollectorDebugLogTests.cs

@@ -0,0 +1,169 @@
+using System;
+using System.Collections.Generic;
+using System.IO;
+using AutopilotMonitor.Agent.V2.Core.Logging;
+using AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.Ime;
+using AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather;
+using AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather.Collectors;
+using AutopilotMonitor.Agent.V2.Core.Tests.Harness;
+using AutopilotMonitor.Shared.Models;
+using Xunit;
+
+namespace AutopilotMonitor.Agent.V2.Core.Tests.Monitoring.Gather
+{
+    /// <summary>
+    /// Debug-trace coverage of <see cref="LogParserCollector"/>: the classic
+    /// "rule delivers nothing" cases must be explained in the trace — zero matches,
+    /// position-tracker skips, and plain-text logs parsed in the default cmtrace mode.
+    /// </summary>
+    public sealed class LogParserCollectorDebugLogTests : IDisposable
+    {
+        private readonly TempDirectory _tmp = new TempDirectory();
+        private readonly List<EnrollmentEvent> _events = new List<EnrollmentEvent>();
+        private readonly GatherRuleContext _context;
+        private readonly string _debugLogPath;
+
+        // %TEMP% lives under C:\Users (hard-blocked) — parse targets sit beside the
+        // test assembly instead, admitted via UnrestrictedMode.
+        private readonly string _outsideUsers = Path.Combine(
+            AppContext.BaseDirectory, "gather-debug-tests-" + Guid.NewGuid().ToString("N"));
+
+        public LogParserCollectorDebugLogTests()
+        {
+            Directory.CreateDirectory(_outsideUsers);
+            var logger = new AgentLogger(_tmp.Path, AgentLogLevel.Info);
+            _debugLogPath = Path.Combine(_tmp.Path, "gather_rules_debug.log");
+            _context = new GatherRuleContext(
+                logger, "sess", "tenant",
+                evt => _events.Add(evt),
+                null,
+                new LogFilePositionTracker(),
+                new GatherRuleDebugLog(_debugLogPath, logger))
+            {
+                UnrestrictedMode = true
+            };
+        }
+
+        public void Dispose()
+        {
+            _tmp.Dispose();
+            try { Directory.Delete(_outsideUsers, recursive: true); } catch { /* best effort */ }
+        }
+
+        private string TraceContent() => File.Exists(_debugLogPath) ? File.ReadAllText(_debugLogPath) : string.Empty;
+
+        private static GatherRule Rule(string target, string pattern, string? format = null) => new GatherRule
+        {
+            RuleId = "GATHER-LP-DEBUG",
+            Title = "logparser debug test",
+            CollectorType = "logparser",
+            Target = target,
+            Parameters = format == null
+                ? new Dictionary<string, string> { ["pattern"] = pattern }
+                : new Dictionary<string, string> { ["pattern"] = pattern, ["format"] = format },
+            Trigger = "startup",
+            OutputEventType = "logparser_debug_test",
+        };
+
+        [Fact]
+        public void ZeroMatches_writes_per_file_outcome_line()
+        {
+            var path = Path.Combine(_outsideUsers, "app.log");
+            File.WriteAllText(path, "nothing interesting\nstill nothing\n");
+
+            new LogParserCollector().Execute(Rule(path, "WILL_NEVER_MATCH_[0-9]+", format: "text"), _context);
+
+            Assert.Empty(_events);
+            var trace = TraceContent();
+            Assert.Contains("app.log: read 2 lines", trace);
+            Assert.Contains("matched 0", trace);
+            Assert.Contains("mode=text", trace);
+        }
+
+        [Fact]
+        public void SecondRun_without_new_content_traces_position_skip()
+        {
+            var path = Path.Combine(_outsideUsers, "twice.log");
+            File.WriteAllText(path, "one line\n");
+            var rule = Rule(path, "one", format: "text");
+
+            var collector = new LogParserCollector();
+            collector.Execute(rule, _context);   // reads the file, advances the position
+            collector.Execute(rule, _context);   // nothing new
+
+            Assert.Contains("twice.log: no new content (position", TraceContent());
+        }
+
+        [Fact]
+        public void PlainTextFile_in_default_cmtrace_mode_gets_format_hint()
+        {
+            var path = Path.Combine(_outsideUsers, "plain.log");
+            File.WriteAllText(path, "plain line one\nplain line two\n");
+
+            new LogParserCollector().Execute(Rule(path, "plain"), _context); // default = cmtrace mode
+
+            Assert.Empty(_events);
+            var trace = TraceContent();
+            Assert.Contains("parseFailures=2", trace);
+            Assert.Contains("every line failed CMTrace parsing — if this is a plain-text log, set parameter format=text", trace);
+        }
+
+        [Fact]
+        public void Match_traces_line_number_matched_text_and_groups()
+        {
+            var path = Path.Combine(_outsideUsers, "match.log");
+            File.WriteAllText(path, "boring line\nError 0x80070005 in setup\n");
+
+            new LogParserCollector().Execute(
+                Rule(path, @"Error (?<code>0x[0-9A-Fa-f]+)", format: "text"), _context);
+
+            Assert.Single(_events);
+            var trace = TraceContent();
+            Assert.Contains("match.log: line 2 matched \"Error 0x80070005\"", trace);
+            Assert.Contains("groups: code=\"0x80070005\"", trace);
+        }
+
+        [Fact]
+        public void MatchTraces_are_capped_per_file()
+        {
+            var path = Path.Combine(_outsideUsers, "many.log");
+            var sb = new System.Text.StringBuilder();
+            for (var i = 1; i <= 15; i++)
+                sb.Append("hit number ").Append(i).Append('\n');
+            File.WriteAllText(path, sb.ToString());
+
+            new LogParserCollector().Execute(Rule(path, "hit", format: "text"), _context);
+
+            Assert.Equal(15, _events.Count); // all matches still emit events
+            var trace = TraceContent();
+            Assert.Contains("many.log: line 10 matched", trace);
+            Assert.Contains("further matches not traced individually", trace);
+            Assert.DoesNotContain("many.log: line 11 matched", trace);
+            Assert.Contains("matched 15", trace); // summary still carries the full count
+        }
+
+        [Fact]
+        public void InvalidRegex_traces_the_pattern_itself()
+        {
+            var path = Path.Combine(_outsideUsers, "irrelevant.log");
+            File.WriteAllText(path, "content\n");
+
+            new LogParserCollector().Execute(Rule(path, "([unclosed", format: "text"), _context);
+
+            Assert.Empty(_events);
+            var trace = TraceContent();
+            Assert.Contains("invalid regex pattern '([unclosed'", trace);
+            Assert.Contains("rule can never match", trace);
+        }
+
+        [Fact]
+        public void MissingFile_traces_no_files_matched()
+        {
+            var path = Path.Combine(_outsideUsers, "does-not-exist.log");
+
+            new LogParserCollector().Execute(Rule(path, "x", format: "text"), _context);
+
+            Assert.Contains("no files matched target", TraceContent());
+        }
+    }
+}

src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/Monitoring/Ime/CmTraceLogParserTests.cs

@@ -1,5 +1,5 @@
 using System;
-using AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.Ime;
+using AutopilotMonitor.Shared.Logging;
 using Xunit;
 
 namespace AutopilotMonitor.Agent.V2.Core.Tests.Monitoring.Ime
@@ -92,6 +92,27 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Monitoring.Ime
             Assert.InRange(entry.Timestamp, before.AddSeconds(-5), after.AddSeconds(5));
         }
 
+        // ── UTC-bias suffix on the time field → honored, not dropped ──────────
+
+        [Theory]
+        [InlineData("+480", 8 * 60)]   // PST writer (UTC-8): UTC = local + 480min
+        [InlineData("-060", -60)]      // UTC+1 writer: UTC = local - 60min
+        public void TryParseLine_applies_utc_bias_suffix(string bias, int expectedOffsetMinutes)
+        {
+            // Session df1fcf47: a writer whose timezone differs from the agent's stamped its
+            // lines with an explicit bias. Without bias handling the line either failed to
+            // match at all (old regex) or would be misread in agent-local time.
+            var line = CmTraceLine("msg", "11:46:19.0226610" + bias, "7-29-2026");
+
+            var ok = CmTraceLogParser.TryParseLine(line, out var entry);
+
+            Assert.True(ok);
+            Assert.Equal(
+                new DateTime(2026, 7, 29, 11, 46, 19, DateTimeKind.Utc).AddTicks(226610).AddMinutes(expectedOffsetMinutes),
+                entry.Timestamp);
+            Assert.Equal(DateTimeKind.Utc, entry.Timestamp.Kind);
+        }
+
         // ── Oversized line → parses, no throw, no truncation of the message ───
 
         [Fact]

src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/Monitoring/Interop/NetshWifiFallbackTests.cs

@@ -0,0 +1,209 @@
+#nullable enable
+using AutopilotMonitor.Agent.V2.Core.Monitoring.Interop;
+using Xunit;
+
+namespace AutopilotMonitor.Agent.V2.Core.Tests.Monitoring.Interop
+{
+    /// <summary>
+    /// Tests for the pure netsh-output parser of the WiFi fallback path. netsh labels follow
+    /// the OS UI language — the parser must extract SSID/signal/radio/channel from the label
+    /// variants of the languages commonly seen in enrollments, and degrade gracefully (fields
+    /// absent, never throw) on unrecognized ones.
+    /// </summary>
+    public sealed class NetshWifiFallbackTests
+    {
+        [Fact]
+        public void Parse_english_output_extracts_all_fields()
+        {
+            const string output = @"
+There is 1 interface on the system:
+
+    Name                   : Wi-Fi
+    Description            : Intel(R) Wi-Fi 6 AX201 160MHz
+    GUID                   : 754b6c07-5ae9-49d5-ba6c-4fbd6e38bbf6
+    State                  : connected
+    SSID                   : contoso-corp
+    AP BSSID               : 3c:37:12:53:c8:44
+    Band                   : 5 GHz
+    Channel                : 116
+    Radio type             : 802.11ax
+    Signal                 : 94%
+";
+            var r = NetshWifiFallback.Parse(output);
+
+            Assert.NotNull(r);
+            Assert.Equal("contoso-corp", r!.Ssid);
+            Assert.Equal(94, r.SignalPercent);
+            Assert.Equal("802.11ax", r.RadioType);
+            Assert.Equal(116, r.Channel);
+        }
+
+        [Fact]
+        public void Parse_german_output_extracts_all_fields()
+        {
+            const string output = @"
+Es ist 1 Schnittstelle auf dem System vorhanden:
+
+    Name                   : WLAN
+    Beschreibung           : Intel(R) Wi-Fi 6 AX201 160MHz
+    Status                 : Verbunden
+    SSID                   : fabrikam-wlan
+    Kanal                  : 44
+    Funktyp                : 802.11ac
+    Signal                 : 87%
+";
+            var r = NetshWifiFallback.Parse(output);
+
+            Assert.NotNull(r);
+            Assert.Equal("fabrikam-wlan", r!.Ssid);
+            Assert.Equal(87, r.SignalPercent);
+            Assert.Equal("802.11ac", r.RadioType);
+            Assert.Equal(44, r.Channel);
+        }
+
+        [Fact]
+        public void Parse_spanish_output_extracts_signal_and_channel()
+        {
+            const string output = @"
+    Nombre                 : Wi-Fi
+    SSID                   : contoso-es
+    Canal                  : 6
+    Tipo de radio          : 802.11n
+    Señal                  : 72%
+";
+            var r = NetshWifiFallback.Parse(output);
+
+            Assert.NotNull(r);
+            Assert.Equal("contoso-es", r!.Ssid);
+            Assert.Equal(72, r.SignalPercent);
+            Assert.Equal("802.11n", r.RadioType);
+            Assert.Equal(6, r.Channel);
+        }
+
+        [Fact]
+        public void Parse_chinese_simplified_output_extracts_all_fields()
+        {
+            const string output = @"
+    名称                   : WLAN
+    SSID                   : contoso-cn
+    信道                   : 149
+    无线电类型             : 802.11ac
+    信号                   : 68%
+";
+            var r = NetshWifiFallback.Parse(output);
+
+            Assert.NotNull(r);
+            Assert.Equal("contoso-cn", r!.Ssid);
+            Assert.Equal(68, r.SignalPercent);
+            Assert.Equal("802.11ac", r.RadioType);
+            Assert.Equal(149, r.Channel);
+        }
+
+        [Fact]
+        public void Parse_korean_output_extracts_all_fields()
+        {
+            const string output = @"
+    이름                   : Wi-Fi
+    SSID                   : contoso-kr
+    채널                   : 36
+    라디오 종류            : 802.11ax
+    신호                   : 91%
+";
+            var r = NetshWifiFallback.Parse(output);
+
+            Assert.NotNull(r);
+            Assert.Equal("contoso-kr", r!.Ssid);
+            Assert.Equal(91, r.SignalPercent);
+            Assert.Equal("802.11ax", r.RadioType);
+            Assert.Equal(36, r.Channel);
+        }
+
+        [Fact]
+        public void Parse_signal_with_space_before_percent_is_parsed()
+        {
+            var r = NetshWifiFallback.Parse("    Signal : 81 %\r\n    SSID : x\r\n");
+
+            Assert.NotNull(r);
+            Assert.Equal(81, r!.SignalPercent);
+        }
+
+        [Fact]
+        public void Parse_ap_bssid_does_not_overwrite_ssid()
+        {
+            const string output = @"
+    SSID                   : contoso-corp
+    AP BSSID               : aa:bb:cc:dd:ee:ff
+";
+            var r = NetshWifiFallback.Parse(output);
+
+            Assert.Equal("contoso-corp", r!.Ssid);
+        }
+
+        [Fact]
+        public void Parse_finnish_output_extracts_all_fields()
+        {
+            const string output = @"
+    Nimi                   : Wi-Fi
+    SSID                   : contoso-fi
+    Kanava                 : 100
+    Radiotyyppi            : 802.11ax
+    Signaali               : 79%
+";
+            var r = NetshWifiFallback.Parse(output);
+
+            Assert.NotNull(r);
+            Assert.Equal("contoso-fi", r!.Ssid);
+            Assert.Equal(79, r.SignalPercent);
+            Assert.Equal("802.11ax", r.RadioType);
+            Assert.Equal(100, r.Channel);
+        }
+
+        [Fact]
+        public void Parse_indonesian_output_extracts_all_fields()
+        {
+            const string output = @"
+    Nama                   : Wi-Fi
+    SSID                   : contoso-id
+    Saluran                : 11
+    Jenis radio            : 802.11n
+    Sinyal                 : 64%
+";
+            var r = NetshWifiFallback.Parse(output);
+
+            Assert.NotNull(r);
+            Assert.Equal("contoso-id", r!.Ssid);
+            Assert.Equal(64, r.SignalPercent);
+            Assert.Equal("802.11n", r.RadioType);
+            Assert.Equal(11, r.Channel);
+        }
+
+        [Fact]
+        public void Parse_unknown_language_without_ssid_returns_null()
+        {
+            // Greek is not in the enrollment-geography label set -> nothing to report.
+            var r = NetshWifiFallback.Parse("    Κατάσταση : συνδεδεμένο\r\n    Σήμα : 90%\r\n");
+
+            Assert.Null(r);
+        }
+
+        [Fact]
+        public void Parse_unknown_language_still_yields_ssid()
+        {
+            // SSID is untranslated in all locales — partial result beats none.
+            var r = NetshWifiFallback.Parse("    SSID : contoso-gr\r\n    Σήμα : 90%\r\n");
+
+            Assert.NotNull(r);
+            Assert.Equal("contoso-gr", r!.Ssid);
+            Assert.Null(r.SignalPercent);
+        }
+
+        [Theory]
+        [InlineData(null)]
+        [InlineData("")]
+        [InlineData("Der WLAN-AutoKonfig-Dienst (wlansvc) wird nicht ausgeführt.")]
+        public void Parse_empty_or_error_output_returns_null(string? output)
+        {
+            Assert.Null(NetshWifiFallback.Parse(output));
+        }
+    }
+}

src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/Monitoring/Interop/WifiInfoReaderTests.cs

@@ -0,0 +1,98 @@
+#nullable enable
+using System.Text;
+using AutopilotMonitor.Agent.V2.Core.Monitoring.Interop;
+using Xunit;
+using static AutopilotMonitor.Agent.V2.Core.Monitoring.Interop.WlanNativeMethods;
+
+namespace AutopilotMonitor.Agent.V2.Core.Tests.Monitoring.Interop
+{
+    /// <summary>
+    /// Tests for the native-WLAN-API WiFi reader. The WLAN state of the test machine is
+    /// unknown (CI runners/VMs have no WLAN service), so the live path only pins the
+    /// fail-soft contract; the pure helpers (SSID decode, PHY-type mapping) are pinned
+    /// exactly — their output feeds wifi_signal_info event payloads and must stay
+    /// consistent with the strings netsh historically reported.
+    /// </summary>
+    public sealed class WifiInfoReaderTests
+    {
+        [Fact]
+        public void TryGetCurrentConnection_never_throws_and_returns_sane_values()
+        {
+            var result = WifiInfoReader.TryGetCurrentConnection();
+
+            if (result != null)
+            {
+                Assert.True(result.SignalPercent.HasValue, "native API path must always carry signal quality");
+                Assert.InRange(result.SignalPercent.Value, 0, 100);
+                if (result.Channel.HasValue)
+                    Assert.True(result.Channel.Value > 0, "channel must be positive when present");
+            }
+        }
+
+        // ----- DecodeSsid ---------------------------------------------------
+
+        [Fact]
+        public void DecodeSsid_decodes_utf8_bytes()
+        {
+            var raw = new byte[32];
+            var ssid = Encoding.UTF8.GetBytes("Contoso-Büro");
+            ssid.CopyTo(raw, 0);
+
+            Assert.Equal("Contoso-Büro", WifiInfoReader.DecodeSsid(raw, (uint)ssid.Length));
+        }
+
+        [Fact]
+        public void DecodeSsid_returns_null_for_empty_or_missing()
+        {
+            Assert.Null(WifiInfoReader.DecodeSsid(null, 5));
+            Assert.Null(WifiInfoReader.DecodeSsid(new byte[32], 0));
+        }
+
+        [Fact]
+        public void DecodeSsid_clamps_length_to_buffer_size()
+        {
+            var raw = Encoding.UTF8.GetBytes("abc");
+
+            // A corrupt native length beyond the buffer must not throw.
+            Assert.Equal("abc", WifiInfoReader.DecodeSsid(raw, 200));
+        }
+
+        [Fact]
+        public void DecodeSsid_uses_only_declared_length()
+        {
+            var raw = new byte[32];
+            Encoding.UTF8.GetBytes("HomeNet-Rest-Ignored").CopyTo(raw, 0);
+
+            Assert.Equal("HomeNet", WifiInfoReader.DecodeSsid(raw, 7));
+        }
+
+        // ----- PhyTypeToRadioType -------------------------------------------
+
+        // int parameters (cast inside): DOT11_PHY_TYPE is internal and may not appear in a
+        // public test method signature (CS0051).
+        [Theory]
+        [InlineData((int)DOT11_PHY_TYPE.dot11_phy_type_ofdm, "802.11a")]
+        [InlineData((int)DOT11_PHY_TYPE.dot11_phy_type_hrdsss, "802.11b")]
+        [InlineData((int)DOT11_PHY_TYPE.dot11_phy_type_erp, "802.11g")]
+        [InlineData((int)DOT11_PHY_TYPE.dot11_phy_type_ht, "802.11n")]
+        [InlineData((int)DOT11_PHY_TYPE.dot11_phy_type_vht, "802.11ac")]
+        [InlineData((int)DOT11_PHY_TYPE.dot11_phy_type_dmg, "802.11ad")]
+        [InlineData((int)DOT11_PHY_TYPE.dot11_phy_type_he, "802.11ax")]
+        [InlineData((int)DOT11_PHY_TYPE.dot11_phy_type_eht, "802.11be")]
+        public void PhyTypeToRadioType_maps_known_generations(int phyType, string expected)
+        {
+            Assert.Equal(expected, WifiInfoReader.PhyTypeToRadioType((DOT11_PHY_TYPE)phyType));
+        }
+
+        [Theory]
+        [InlineData((int)DOT11_PHY_TYPE.dot11_phy_type_unknown)]
+        [InlineData((int)DOT11_PHY_TYPE.dot11_phy_type_fhss)]
+        [InlineData((int)DOT11_PHY_TYPE.dot11_phy_type_dsss)]
+        [InlineData((int)DOT11_PHY_TYPE.dot11_phy_type_irbaseband)]
+        [InlineData(9999)]
+        public void PhyTypeToRadioType_returns_null_for_legacy_or_unknown(int phyType)
+        {
+            Assert.Null(WifiInfoReader.PhyTypeToRadioType((DOT11_PHY_TYPE)phyType));
+        }
+    }
+}

src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/Monitoring/Runtime/DiagnosticsPackageServiceTests.cs

@@ -226,6 +226,95 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Monitoring.Runtime
             return archive.Entries.Select(e => e.FullName).ToArray();
         }
 
+        private static string ZipEntryText(byte[] zipBytes, string entryName)
+        {
+            using var ms = new MemoryStream(zipBytes);
+            using var archive = new ZipArchive(ms, ZipArchiveMode.Read);
+            var entry = archive.GetEntry(entryName);
+            Assert.NotNull(entry);
+            using var reader = new StreamReader(entry!.Open(), Encoding.UTF8);
+            return reader.ReadToEnd();
+        }
+
+        // ── Nullable outcome (on-demand mid-session) — gate + sessioninfo semantics ──
+
+        /// <summary>
+        /// Sentinel subclass: throws before any HTTP so gate-pass-through is observable as a
+        /// non-null error result (a skip returns null BEFORE the archive is ever built).
+        /// </summary>
+        private sealed class ThrowOnBuildService : DiagnosticsPackageService
+        {
+            public ThrowOnBuildService(AgentConfiguration cfg, AgentLogger logger, BackendApiClient api)
+                : base(cfg, logger, api) { }
+            internal override byte[] BuildArchiveBytes(bool? enrollmentSucceeded) =>
+                throw new System.InvalidOperationException("gate-passed-sentinel");
+        }
+
+        private static DiagnosticsPackageService BuildGateProbe(AgentLogger logger, string mode)
+        {
+            var cfg = Cfg();
+            cfg.DiagnosticsUploadEnabled = true;
+            cfg.DiagnosticsUploadMode = mode;
+            var apiClient = new BackendApiClient(
+                httpClient: new System.Net.Http.HttpClient(),
+                baseUrl: "http://localhost",
+                manufacturer: string.Empty,
+                model: string.Empty,
+                serialNumber: string.Empty,
+                useBootstrapTokenAuth: false,
+                bootstrapToken: null,
+                agentVersion: "0.0.0",
+                logger: logger);
+            return new ThrowOnBuildService(cfg, logger, apiClient);
+        }
+
+        [Fact]
+        public async System.Threading.Tasks.Task CreateAndUploadAsync_null_outcome_passes_OnFailure_gate()
+        {
+            // On-demand mid-session (no outcome yet): the OnFailure gate must NOT skip —
+            // there is no known success to skip on. Reaching the archive build (sentinel
+            // throw → error result) proves the gate was passed; a skip would return null.
+            using var rig = new Rig();
+            var result = await BuildGateProbe(rig.Logger, "OnFailure")
+                .CreateAndUploadAsync(enrollmentSucceeded: null, fileNameSuffix: "server-requested");
+
+            Assert.NotNull(result);
+            Assert.Equal("gate-passed-sentinel", result!.ErrorCode);
+        }
+
+        [Fact]
+        public async System.Threading.Tasks.Task CreateAndUploadAsync_known_success_still_skipped_by_OnFailure_gate()
+        {
+            using var rig = new Rig();
+            var result = await BuildGateProbe(rig.Logger, "OnFailure")
+                .CreateAndUploadAsync(enrollmentSucceeded: true);
+
+            Assert.Null(result);
+        }
+
+        [Fact]
+        public async System.Threading.Tasks.Task CreateAndUploadAsync_null_outcome_still_blocked_by_mode_Off()
+        {
+            using var rig = new Rig();
+            var result = await BuildGateProbe(rig.Logger, "Off")
+                .CreateAndUploadAsync(enrollmentSucceeded: null);
+
+            Assert.Null(result);
+        }
+
+        [Theory]
+        [InlineData(true, "Succeeded")]
+        [InlineData(false, "Failed")]
+        [InlineData(null, "In Progress")]
+        public void BuildArchiveBytes_sessioninfo_reflects_nullable_outcome(bool? outcome, string expected)
+        {
+            using var rig = new Rig();
+            var bytes = rig.Build().BuildArchiveBytes(outcome);
+
+            var sessionInfo = ZipEntryText(bytes, "sessioninfo.txt");
+            Assert.Contains($"Enrollment Result: {expected}", sessionInfo);
+        }
+
         // ── BuildBlobUploadUrl — destination-aware URL construction ─────────────────
 
         [Theory]

src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/Monitoring/SystemSignals/ModernDeploymentTrackerErrorBackfillTests.cs

@@ -112,6 +112,36 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Monitoring.SystemSignals
             Assert.Equal(false, data["backfilled"]);
         }
 
+        [Fact]
+        public void ErrorBackfillSummary_EmitsInfoLogEvent_AnnouncingTheReplayBlock()
+        {
+            _tracker.EmitErrorBackfillSummary(replayedCount: 6, droppedOverCap: 0);
+
+            var posted = _sink.Posted.Single(p => p.Kind == DecisionSignalKind.InformationalEvent);
+            Assert.Equal("modern_deployment_log", posted.Payload![SignalPayloadKeys.EventType]);
+
+            var data = Assert.IsAssignableFrom<IReadOnlyDictionary<string, object>>(posted.TypedPayload);
+            Assert.Equal(true, data["backfillSummary"]);
+            Assert.Equal(6, data["replayedCount"]);
+            Assert.Equal(0, data["droppedOverCap"]);
+            Assert.Equal(240, data["lookbackMinutes"]);
+
+            var message = (string)posted.Payload[SignalPayloadKeys.Message];
+            Assert.Contains("Replaying 6 error event(s)", message);
+            Assert.Contains("before the agent started", message);
+            Assert.DoesNotContain("cap", message);
+        }
+
+        [Fact]
+        public void ErrorBackfillSummary_MentionsDroppedRecords_WhenCapWasHit()
+        {
+            _tracker.EmitErrorBackfillSummary(replayedCount: 25, droppedOverCap: 7);
+
+            var posted = _sink.Posted.Single(p => p.Kind == DecisionSignalKind.InformationalEvent);
+            var message = (string)posted.Payload![SignalPayloadKeys.Message];
+            Assert.Contains("7 older record(s) beyond the 25-record cap", message);
+        }
+
         [Fact]
         public void BackfilledHarmlessId_StillRunsThroughRollupSuppression()
         {

src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/Orchestration/EnrollmentOrchestratorEventBridgeTests.cs

@@ -54,6 +54,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Orchestration
             public ISignalIngressSink? CapturedIngress { get; private set; }
             public IClock? CapturedClock { get; private set; }
             public AutopilotMonitor.Agent.V2.Core.Transport.Telemetry.ITelemetrySpool? CapturedTelemetrySpool { get; private set; }
+            public TimelineEventStream? CapturedTimelineEvents { get; private set; }
 
             public CollectorSurfaces CreateCollectorHosts(
                 string sessionId,
@@ -62,12 +63,14 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Orchestration
                 IReadOnlyCollection<string> whiteGloveSealingPatternIds,
                 ISignalIngressSink ingress,
                 IClock clock,
-                AutopilotMonitor.Agent.V2.Core.Transport.Telemetry.ITelemetrySpool? telemetrySpool)
+                AutopilotMonitor.Agent.V2.Core.Transport.Telemetry.ITelemetrySpool? telemetrySpool,
+                TimelineEventStream? timelineEvents = null)
             {
                 CapturedWhiteGloveSealingPatternIds = whiteGloveSealingPatternIds;
                 CapturedIngress = ingress;
                 CapturedClock = clock;
                 CapturedTelemetrySpool = telemetrySpool;
+                CapturedTimelineEvents = timelineEvents;
                 foreach (var name in HostNames)
                 {
                     Hosts.Add(new FakeCollectorHost(name));

src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/Orchestration/EnrollmentOrchestratorWhiteGlovePatternTests.cs

@@ -27,7 +27,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Orchestration
                 IReadOnlyCollection<string> whiteGloveSealingPatternIds,
                 ISignalIngressSink ingress,
                 IClock clock,
-                AutopilotMonitor.Agent.V2.Core.Transport.Telemetry.ITelemetrySpool? telemetrySpool)
+                AutopilotMonitor.Agent.V2.Core.Transport.Telemetry.ITelemetrySpool? telemetrySpool,
+                TimelineEventStream? timelineEvents = null)
             {
                 CapturedPatternIds = whiteGloveSealingPatternIds;
                 return new CollectorSurfaces(Array.Empty<ICollectorHost>());

src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/Orchestration/GatherRuleExecutorHostTimelineFeedTests.cs

@@ -0,0 +1,189 @@
+#nullable enable
+using System;
+using System.Collections.Generic;
+using System.Diagnostics;
+using System.Threading;
+using AutopilotMonitor.Agent.V2.Core.Logging;
+using AutopilotMonitor.Agent.V2.Core.Orchestration;
+using AutopilotMonitor.Agent.V2.Core.Tests.Harness;
+using AutopilotMonitor.DecisionCore.Engine;
+using AutopilotMonitor.DecisionCore.Signals;
+using AutopilotMonitor.Shared.Models;
+using Xunit;
+
+namespace AutopilotMonitor.Agent.V2.Core.Tests.Orchestration
+{
+    /// <summary>
+    /// GatherRuleExecutorHost feeds its phase_change / phase_exit / on_event triggers from the
+    /// POST-REDUCE <see cref="TimelineEventStream"/> (emitted timeline events), not from raw
+    /// signals. Regression anchor: session 32312a32 (rsneuffen.de) — a phase_change rule on
+    /// FinalizingSetup fired at the raw EspPhaseChanged(FinalizingSetup) signal (ESP exit),
+    /// 7 minutes before the engine's RealmJoin-gated phase_transition(FinalizingSetup), and read
+    /// a registry key before the RealmJoin package wrote it. With the timeline feed the rule
+    /// fires only when the phase declaration is actually emitted.
+    /// Rules use the absent-registry-path pattern so no real system state is touched; execution
+    /// is observed via the InformationalEvent posts the host sends through its ingress sink.
+    /// </summary>
+    [Collection("SerialThreading")] // rules execute on the shared ThreadPool
+    public sealed class GatherRuleExecutorHostTimelineFeedTests : IDisposable
+    {
+        private const string AbsentPath =
+            "HKLM\\SOFTWARE\\AutopilotMonitorTests\\DefinitelyAbsent_5b1f03a2-0000-0000-0000-000000000000";
+
+        private readonly TempDirectory _tmp = new TempDirectory();
+        private readonly CapturingSink _sink = new CapturingSink();
+        private readonly TimelineEventStream _stream = new TimelineEventStream();
+        private GatherRuleExecutorHost? _host;
+
+        public void Dispose()
+        {
+            _host?.Dispose();
+            _tmp.Dispose();
+        }
+
+        private sealed class CapturingSink : ISignalIngressSink
+        {
+            private readonly List<string> _eventTypes = new List<string>();
+            private readonly object _gate = new object();
+
+            public int CountOf(string eventType)
+            {
+                lock (_gate)
+                {
+                    var n = 0;
+                    foreach (var t in _eventTypes)
+                        if (string.Equals(t, eventType, StringComparison.Ordinal)) n++;
+                    return n;
+                }
+            }
+
+            public void Post(
+                DecisionSignalKind kind,
+                DateTime occurredAtUtc,
+                string sourceOrigin,
+                Evidence evidence,
+                IReadOnlyDictionary<string, string>? payload = null,
+                int kindSchemaVersion = 1,
+                object? typedPayload = null)
+            {
+                if (kind != DecisionSignalKind.InformationalEvent || payload == null) return;
+                if (!payload.TryGetValue(SignalPayloadKeys.EventType, out var eventType)) return;
+                lock (_gate) _eventTypes.Add(eventType);
+            }
+        }
+
+        private void BuildHost(params GatherRule[] rules)
+        {
+            var logger = new AgentLogger(_tmp.Path, AgentLogLevel.Info);
+            _host = new GatherRuleExecutorHost(
+                sessionId: "sess",
+                tenantId: "tenant",
+                ingress: _sink,
+                clock: new SystemClock(),
+                logger: logger,
+                rules: new List<GatherRule>(rules),
+                imeLogPathOverride: null,
+                unrestrictedMode: true,
+                gatherDebugLogPath: null,
+                timelineEvents: _stream);
+            _host.Start();
+        }
+
+        private bool WaitForCount(string eventType, int count, int timeoutMs = 10000)
+        {
+            var sw = Stopwatch.StartNew();
+            while (sw.ElapsedMilliseconds < timeoutMs)
+            {
+                if (_sink.CountOf(eventType) >= count) return true;
+                Thread.Sleep(25);
+            }
+            return _sink.CountOf(eventType) >= count;
+        }
+
+        private static GatherRule Rule(string id, string trigger, string? triggerPhase = null, string? triggerEventType = null)
+            => new GatherRule
+            {
+                RuleId = id,
+                Title = id,
+                CollectorType = "registry",
+                Target = AbsentPath,
+                Trigger = trigger,
+                TriggerPhase = triggerPhase ?? string.Empty,
+                TriggerEventType = triggerEventType ?? string.Empty,
+                OutputEventType = "gather_host_test",
+                Enabled = true,
+            };
+
+        [Fact]
+        public void PhaseChangeRule_FiresOnEmittedPhaseDeclaration_NotOnPhaselessEvents()
+        {
+            BuildHost(Rule("GATHER-HOST-001", "phase_change", triggerPhase: "FinalizingSetup"));
+
+            // The raw-world sequence of session 32312a32 as it reaches the emitted timeline:
+            // esp_exiting and hello_wizard_started are emitted WITHOUT a phase declaration
+            // (the engine holds FinalizingSetup back behind the RealmJoin gate) — no fire.
+            _stream.Publish("esp_exiting", EnrollmentPhase.Unknown);
+            _stream.Publish("hello_wizard_started", EnrollmentPhase.Unknown);
+            Thread.Sleep(300);
+            Assert.Equal(0, _sink.CountOf("gather_host_test"));
+
+            // Only the engine's actual phase declaration fires the rule.
+            _stream.Publish("phase_transition", EnrollmentPhase.FinalizingSetup);
+            Assert.True(WaitForCount("gather_host_test", 1));
+        }
+
+        [Fact]
+        public void OnEventRule_FiresForEngineEmittedEventTypes()
+        {
+            // enrollment_complete is an engine-emitted effect event; it never existed on the raw
+            // InformationalEvent signal stream, so the docs-promised "On Event with
+            // enrollment_complete" trigger was dead under the previous SignalPosted feed.
+            BuildHost(Rule("GATHER-HOST-002", "on_event", triggerEventType: "enrollment_complete"));
+
+            _stream.Publish("enrollment_complete", EnrollmentPhase.Unknown);
+            Assert.True(WaitForCount("gather_host_test", 1));
+        }
+
+        [Fact]
+        public void PhaseFeed_DedupsConsecutiveSamePhaseDeclarations()
+        {
+            // "Any phase" phase_change rule fires on every phase TRANSITION — a re-declared
+            // identical phase (e.g. duplicate esp_phase_changed) must not count as one.
+            BuildHost(Rule("GATHER-HOST-003", "phase_change", triggerPhase: ""));
+
+            _stream.Publish("esp_phase_changed", EnrollmentPhase.DeviceSetup);
+            Assert.True(WaitForCount("gather_host_test", 1));
+
+            _stream.Publish("esp_phase_changed", EnrollmentPhase.DeviceSetup);
+            Thread.Sleep(300);
+            Assert.Equal(1, _sink.CountOf("gather_host_test"));
+
+            _stream.Publish("esp_phase_changed", EnrollmentPhase.AccountSetup);
+            Assert.True(WaitForCount("gather_host_test", 2));
+        }
+
+        [Fact]
+        public void PhaseExitRule_FiresWhenEmittedTimelineLeavesThePhase()
+        {
+            BuildHost(Rule("GATHER-HOST-004", "phase_exit", triggerPhase: "AccountSetup"));
+
+            _stream.Publish("esp_phase_changed", EnrollmentPhase.AccountSetup);
+            Thread.Sleep(300);
+            Assert.Equal(0, _sink.CountOf("gather_host_test"));
+
+            _stream.Publish("phase_transition", EnrollmentPhase.FinalizingSetup);
+            Assert.True(WaitForCount("gather_host_test", 1));
+        }
+
+        [Fact]
+        public void StoppedHost_NoLongerReactsToTheStream()
+        {
+            BuildHost(Rule("GATHER-HOST-005", "on_event", triggerEventType: "enrollment_complete"));
+
+            _host!.Stop();
+            _stream.Publish("enrollment_complete", EnrollmentPhase.Unknown);
+            Thread.Sleep(300);
+            Assert.Equal(0, _sink.CountOf("gather_host_test"));
+        }
+    }
+}

src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/Program/PostEnrollmentFactsObservedSignalTests.cs

@@ -66,6 +66,11 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Program
             // same facts signal (safe default "false" off-device).
             var selfDeploying = payload["isSelfDeployingProfile"];
             Assert.True(selfDeploying == "true" || selfDeploying == "false");
+            // W365 — the Cloud PC marker fact rides the same signal (safe default "false"
+            // off-device; a build host is not a Cloud PC).
+            Assert.Contains("isCloudPc", (IDictionary<string, string>)payload);
+            var cloudPc = payload["isCloudPc"];
+            Assert.True(cloudPc == "true" || cloudPc == "false");
         }
 
         [Fact]

src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/Security/CloudPcDetectorTests.cs

@@ -0,0 +1,74 @@
+using System;
+using System.Collections.Generic;
+using AutopilotMonitor.Agent.V2.Core.Security;
+using Xunit;
+
+namespace AutopilotMonitor.Agent.V2.Core.Tests.Security
+{
+    /// <summary>
+    /// Pins the marker-AND contract of <see cref="CloudPcDetector.ResolveIsCloudPc"/>: BOTH
+    /// the Windows365 registry key and the CloudManagedDesktopExtension service key must be
+    /// present — each alone has plausible look-alikes (W365-Boot physical clients carry
+    /// Windows365 policy state; the MCMD agent family served other managed-desktop
+    /// offerings). Mirrors the bootstrap script's field-verified <c>Test-IsCloudPc</c>.
+    /// </summary>
+    public sealed class CloudPcDetectorTests
+    {
+        private static Func<string, bool> Probe(params string[] existingKeys)
+        {
+            var set = new HashSet<string>(existingKeys, StringComparer.OrdinalIgnoreCase);
+            return path => set.Contains(path);
+        }
+
+        [Fact]
+        public void Both_markers_present_resolves_true()
+        {
+            Assert.True(CloudPcDetector.ResolveIsCloudPc(Probe(
+                CloudPcDetector.Windows365MarkerKey,
+                CloudPcDetector.CmdeServiceKey)));
+        }
+
+        [Fact]
+        public void Windows365_key_alone_resolves_false()
+        {
+            // W365-Boot physical client shape: policy state without the on-device MCMD agent.
+            Assert.False(CloudPcDetector.ResolveIsCloudPc(Probe(CloudPcDetector.Windows365MarkerKey)));
+        }
+
+        [Fact]
+        public void Cmde_service_alone_resolves_false()
+        {
+            // MCMD agent family also served other managed-desktop offerings.
+            Assert.False(CloudPcDetector.ResolveIsCloudPc(Probe(CloudPcDetector.CmdeServiceKey)));
+        }
+
+        [Fact]
+        public void No_markers_resolves_false()
+        {
+            Assert.False(CloudPcDetector.ResolveIsCloudPc(Probe()));
+        }
+
+        [Fact]
+        public void Null_probe_resolves_false()
+        {
+            Assert.False(CloudPcDetector.ResolveIsCloudPc(null));
+        }
+
+        [Fact]
+        public void Throwing_probe_degrades_to_false()
+        {
+            // SKIP-safe contract: a broken registry read must never classify, let alone throw.
+            Assert.False(CloudPcDetector.ResolveIsCloudPc(_ => throw new UnauthorizedAccessException("registry denied")));
+        }
+
+        [Fact]
+        public void DetectIsCloudPc_never_throws_on_build_host()
+        {
+            // Real-registry shell: exercises the exception-swallowing wrapper end to end.
+            // A build host is not a Cloud PC, but the contract under test is "no throw",
+            // not the detected value.
+            var ex = Record.Exception(() => CloudPcDetector.DetectIsCloudPc());
+            Assert.Null(ex);
+        }
+    }
+}

src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/Security/SessionRegistrationHelperTests.cs

@@ -137,6 +137,10 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Security
             Assert.Equal(Environment.MachineName, captured.DeviceName);
             Assert.False(string.IsNullOrEmpty(captured.EnrollmentType));
             Assert.True(captured.IsUserDriven);
+            // W365 marker rides the registration body. A build host is not a Cloud PC
+            // (marker-AND: Windows365 key + CloudManagedDesktopExtension service), so the
+            // detector's SKIP-safe default is what must land here.
+            Assert.False(captured.IsCloudPc);
         }
 
         [Fact]

src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/SignalAdapters/ImeLogTrackerAdapterHistoricAppReplayTests.cs

@@ -83,13 +83,36 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.SignalAdapters
             using var adapter = new ImeLogTrackerAdapter(f.Tracker, f.Ingress, f.Clock);
             var app = new AppPackageState("app-do", 0);
 
-            f.Tracker.LastMatchedLogTimestamp = ClockNow.AddDays(-7);
-            adapter.TriggerDoTelemetryFromTest(app);
+            // Line-grounded path: the [DO TEL] line's own timestamp travels with the callback.
+            adapter.TriggerDoTelemetryFromTest(app, ClockNow.AddDays(-7));
             Assert.Empty(f.InfoEvents(SharedEventTypes.DoTelemetry));
 
-            f.Tracker.LastMatchedLogTimestamp = ClockNow.AddMinutes(-1);
-            adapter.TriggerDoTelemetryFromTest(app);
-            Assert.Single(f.InfoEvents(SharedEventTypes.DoTelemetry));
+            adapter.TriggerDoTelemetryFromTest(app, ClockNow.AddMinutes(-1));
+            var info = Assert.Single(f.InfoEvents(SharedEventTypes.DoTelemetry));
+            Assert.Equal(ClockNow.AddMinutes(-1), info.OccurredAtUtc);
+        }
+
+        [Fact]
+        public void Poll_driven_do_telemetry_stamps_clock_ignoring_unrelated_last_matched_line()
+        {
+            // Session df1fcf47: the DO collector observed the completion live, but the event
+            // inherited LastMatchedLogTimestamp from an unrelated, tz-skewed log line 8h in
+            // the past — which dragged Sessions.StartedAt back and inflated the duration.
+            // Poll-driven telemetry (null source timestamp) must stamp the clock, never the
+            // last matched line.
+            using var f = new ImeLogTrackerAdapterFixture(ClockNow);
+            using var adapter = new ImeLogTrackerAdapter(f.Tracker, f.Ingress, f.Clock);
+            var app = new AppPackageState("app-do-poll", 0);
+
+            f.Tracker.LastMatchedLogTimestamp = ClockNow.AddHours(-8);
+            adapter.TriggerDoTelemetryFromTest(app, sourceTimestampUtc: null);
+
+            var info = Assert.Single(f.InfoEvents(SharedEventTypes.DoTelemetry));
+            Assert.Equal(ClockNow, info.OccurredAtUtc);
+            Assert.Equal("true", info.Payload!["derivedTimestamp"]);
+            // Not a replay — live observation must never trip the replay suppression,
+            // even with a stale unrelated line on the tracker.
+            Assert.Empty(f.InfoEvents(SharedEventTypes.HistoricImeReplayDetected));
         }
 
         [Fact]

src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/SignalAdapters/ImeLogTrackerAdapterTests.cs

@@ -647,13 +647,13 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.SignalAdapters
             int priorDoCalls = 0;
             int priorScriptCalls = 0;
             f.Tracker.OnImeAgentVersion = _ => priorVersionCalls++;
-            f.Tracker.OnDoTelemetryReceived = _ => priorDoCalls++;
+            f.Tracker.OnDoTelemetryReceived = (_, _) => priorDoCalls++;
             f.Tracker.OnScriptCompleted = _ => priorScriptCalls++;
 
             using var adapter = new ImeLogTrackerAdapter(f.Tracker, f.Ingress, f.Clock);
 
             f.Tracker.OnImeAgentVersion("1.0.0.0");
-            f.Tracker.OnDoTelemetryReceived(new AppPackageState("app-1", 0));
+            f.Tracker.OnDoTelemetryReceived(new AppPackageState("app-1", 0), null);
             f.Tracker.OnScriptCompleted(new ScriptExecutionState { PolicyId = "p", ScriptType = "platform" });
 
             Assert.Equal(1, priorVersionCalls);
@@ -667,7 +667,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.SignalAdapters
         {
             using var f = new ImeLogTrackerAdapterFixture();
             Action<string> priorVersion = _ => { };
-            Action<AppPackageState> priorDo = _ => { };
+            Action<AppPackageState, DateTime?> priorDo = (_, _) => { };
             Action<ScriptExecutionState> priorScript = _ => { };
             f.Tracker.OnImeAgentVersion = priorVersion;
             f.Tracker.OnDoTelemetryReceived = priorDo;

src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/Telemetry/Events/EventTimelineEmitterTests.cs

@@ -153,6 +153,58 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Telemetry.Events
             Assert.Equal("Device Setup", (string?)parsed["PhaseName"]);
         }
 
+        [Fact]
+        public void Emit_publishes_eventType_and_parsed_phase_to_TimelineEventStream()
+        {
+            // Post-reduce observer surface: gather-rule phase/event triggers subscribe here so
+            // they fire in step with what the timeline shows (session 32312a32 regression).
+            using var r = new Rig();
+            var stream = new AutopilotMonitor.Agent.V2.Core.Orchestration.TimelineEventStream();
+            var published = new List<(string EventType, EnrollmentPhase Phase)>();
+            stream.EventEmitted += (eventType, phase) => published.Add((eventType, phase));
+            var sut = new EventTimelineEmitter(r.Inner, stream);
+
+            sut.Emit(
+                new Dictionary<string, string>
+                {
+                    ["eventType"] = "phase_transition",
+                    ["phase"] = "FinalizingSetup",
+                },
+                State(),
+                At);
+            sut.Emit(
+                new Dictionary<string, string> { ["eventType"] = "enrollment_complete" },
+                State(),
+                At);
+
+            Assert.Equal(2, published.Count);
+            Assert.Equal(("phase_transition", EnrollmentPhase.FinalizingSetup), published[0]);
+            Assert.Equal(("enrollment_complete", EnrollmentPhase.Unknown), published[1]);
+            // Publish happens AFTER the transport enqueue — wire ordering is authoritative.
+            Assert.Equal(2, r.Transport.EnqueueCount);
+        }
+
+        [Fact]
+        public void TimelineEventStream_subscriber_exception_does_not_break_the_emit_path()
+        {
+            using var r = new Rig();
+            var stream = new AutopilotMonitor.Agent.V2.Core.Orchestration.TimelineEventStream();
+            var secondSubscriberCalls = 0;
+            stream.EventEmitted += (_, _) => throw new InvalidOperationException("subscriber bug");
+            stream.EventEmitted += (_, _) => secondSubscriberCalls++;
+            var sut = new EventTimelineEmitter(r.Inner, stream);
+
+            sut.Emit(
+                new Dictionary<string, string> { ["eventType"] = "enrollment_complete" },
+                State(),
+                At);
+
+            // Emit neither threw (would surface as an EffectRunner retry = duplicated event)
+            // nor skipped the remaining subscribers.
+            Assert.Equal(1, r.Transport.EnqueueCount);
+            Assert.Equal(1, secondSubscriberCalls);
+        }
+
         [Fact]
         public void Phase_parameter_with_invalid_value_falls_back_to_Unknown()
         {

src/Agent/AutopilotMonitor.Agent.V2.Core.Tests/Termination/EnrollmentTerminationHandlerTests.cs

@@ -511,6 +511,88 @@ namespace AutopilotMonitor.Agent.V2.Core.Tests.Termination
                 $"network_bandwidth_estimate (@{bandwidthIdx}) must precede whiteglove_part1_complete (@{part1CompleteIdx}) so the straggler stays in Part 1.");
         }
 
+        // ===================================================== WG Part-1 preprov diagnostics
+        // V1 parity (restored 2026-07-28): the seal exit uploads the diagnostics package as a
+        // pre-provisioning intermediate under the SAME mode gating as the terminal path — the
+        // seal counts as a success, so Always uploads, OnFailure skips (a Part-1 failure
+        // terminates via the regular Failed path, which uploads), Off does nothing.
+
+        [Theory]
+        [InlineData("Always", true, 1)]
+        [InlineData("OnFailure", true, 0)]
+        [InlineData("Off", true, 0)]
+        [InlineData("Always", false, 0)]
+        public void Handle_whiteglove_part1_diagnostics_upload_respects_mode(
+            string mode, bool enabled, int expected)
+        {
+            using var rig = new Rig();
+            rig.State = new DecisionStateBuilder(DecisionState.CreateInitial("S1", "T1")) { Stage = SessionStage.WhiteGloveSealed }.Build();
+            var cfg = rig.BuildConfig(diagEnabled: enabled, diagMode: mode);
+
+            rig.Build(cfg).Handle(sender: null!,
+                Args(EnrollmentTerminationReason.DecisionTerminalStage, EnrollmentTerminationOutcome.Succeeded, SessionStage.WhiteGloveSealed));
+
+            Assert.Equal(expected, rig.DiagnosticsUploads);
+        }
+
+        [Fact]
+        public void Handle_whiteglove_part1_diagnostics_upload_uses_preprov_suffix_and_succeeded_flag()
+        {
+            using var rig = new Rig();
+            rig.State = new DecisionStateBuilder(DecisionState.CreateInitial("S1", "T1")) { Stage = SessionStage.WhiteGloveSealed }.Build();
+            var cfg = rig.BuildConfig(diagEnabled: true, diagMode: "Always");
+
+            rig.Build(cfg).Handle(sender: null!,
+                Args(EnrollmentTerminationReason.DecisionTerminalStage, EnrollmentTerminationOutcome.Succeeded, SessionStage.WhiteGloveSealed));
+
+            Assert.Equal(1, rig.DiagnosticsUploads);
+            Assert.Equal("preprov", rig.LastDiagnosticsSuffix);
+            Assert.Equal(true, rig.LastDiagnosticsSucceededFlag);
+        }
+
+        [Fact]
+        public void Handle_whiteglove_part1_diagnostics_events_precede_part1_complete_marker()
+        {
+            // whiteglove_part1_complete is the authoritative Part-1/Part-2 boundary for the
+            // web split (computeWhiteGloveSplitSequence) — diagnostics_collecting/uploaded
+            // must sequence BEFORE it or they get mis-filed into the resumed Part-2 block.
+            using var rig = new Rig();
+            rig.State = new DecisionStateBuilder(DecisionState.CreateInitial("S1", "T1")) { Stage = SessionStage.WhiteGloveSealed }.Build();
+            rig.DiagnosticsResult = new DiagnosticsUploadResult { BlobName = "diag-preprov.zip" };
+            var cfg = rig.BuildConfig(diagEnabled: true, diagMode: "Always");
+
+            rig.Build(cfg).Handle(sender: null!,
+                Args(EnrollmentTerminationReason.DecisionTerminalStage, EnrollmentTerminationOutcome.Succeeded, SessionStage.WhiteGloveSealed));
+
+            var emitted = rig.EmittedEventTypes.ToList();
+            var collectingIdx = emitted.IndexOf("diagnostics_collecting");
+            var uploadedIdx = emitted.IndexOf("diagnostics_uploaded");
+            var part1CompleteIdx = emitted.IndexOf(Constants.EventTypes.WhiteGlovePart1Complete);
+
+            Assert.True(collectingIdx >= 0, "diagnostics_collecting must have been emitted.");
+            Assert.True(uploadedIdx >= 0, "diagnostics_uploaded must have been emitted.");
+            Assert.True(part1CompleteIdx >= 0, "whiteglove_part1_complete must have been emitted.");
+            Assert.True(uploadedIdx < part1CompleteIdx,
+                $"diagnostics_uploaded (@{uploadedIdx}) must precede whiteglove_part1_complete (@{part1CompleteIdx}) so the upload stays in Part 1.");
+        }
+
+        [Fact]
+        public void Handle_whiteglove_part1_still_skips_cleanup_and_marker_when_diagnostics_enabled()
+        {
+            // The preprov upload must not change the Part-1 exit contract: no self-destruct,
+            // no enrollment-complete.marker, whiteglove.complete still written.
+            using var rig = new Rig();
+            rig.State = new DecisionStateBuilder(DecisionState.CreateInitial("S1", "T1")) { Stage = SessionStage.WhiteGloveSealed }.Build();
+            var cfg = rig.BuildConfig(diagEnabled: true, diagMode: "Always");
+
+            rig.Build(cfg).Handle(sender: null!,
+                Args(EnrollmentTerminationReason.DecisionTerminalStage, EnrollmentTerminationOutcome.Succeeded, SessionStage.WhiteGloveSealed));
+
+            Assert.Equal(0, rig.CleanupService.Invocations);
+            Assert.False(File.Exists(Path.Combine(rig.StateDir, "enrollment-complete.marker")));
+            Assert.True(rig.SessionPersistence.IsWhiteGloveResume());
+        }
+
         [Fact]
         public void Handle_standalone_reboot_fires_when_reboot_enabled_and_no_self_destruct()
         {

src/Agent/AutopilotMonitor.Agent.V2.Core/Configuration/AgentConfiguration.cs

@@ -121,6 +121,13 @@ namespace AutopilotMonitor.Agent.V2.Core.Configuration
         /// </summary>
         public string ImeMatchLogPath { get; set; }
 
+        /// <summary>
+        /// Optional path to write a gather-rule evaluation trace (for debugging).
+        /// If empty, no trace is written. Set from remote config (EnableGatherRuleDebugLog)
+        /// or the --gather-debug-log CLI override.
+        /// </summary>
+        public string GatherRuleDebugLogPath { get; set; }
+
         /// <summary>
         /// Path to directory with real IME log files for log replay.
         /// When set, the agent replays these logs with time compression instead of reading live logs.

src/Agent/AutopilotMonitor.Agent.V2.Core/Configuration/RemoteConfigMerger.cs

@@ -135,6 +135,24 @@ namespace AutopilotMonitor.Agent.V2.Core.Configuration
                 }
             }
 
+            // ---------------- GatherRuleDebugLog: same bool→path projection as ImeMatchLog
+            //                  above. `true` expands Constants.GatherRuleDebugLogPath, `false`
+            //                  nulls the runtime path unless a --gather-debug-log CLI override
+            //                  supplied a non-default path.
+            if (remoteConfig.EnableGatherRuleDebugLog)
+            {
+                agentConfig.GatherRuleDebugLogPath = Environment.ExpandEnvironmentVariables(Constants.GatherRuleDebugLogPath);
+            }
+            else
+            {
+                var defaultGatherDebugPath = Environment.ExpandEnvironmentVariables(Constants.GatherRuleDebugLogPath);
+                if (string.IsNullOrEmpty(agentConfig.GatherRuleDebugLogPath)
+                    || string.Equals(agentConfig.GatherRuleDebugLogPath, defaultGatherDebugPath, StringComparison.OrdinalIgnoreCase))
+                {
+                    agentConfig.GatherRuleDebugLogPath = null;
+                }
+            }
+
             // ---------------- Upload interval / batch — direct, V1 parity (no > 0 gate so a
             //                  misconfigured tenant can in theory break uploads, but this
             //                  surfaces the config bug instead of silently masking it).

src/Agent/AutopilotMonitor.Agent.V2.Core/Configuration/RemoteConfigService.cs

@@ -327,6 +327,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Configuration
                 KeepLogFile = false,
                 EnableGeoLocation = true,
                 EnableImeMatchLog = false,
+                EnableGatherRuleDebugLog = false,
                 Collectors = CollectorConfiguration.CreateDefault(),
                 GatherRules = new System.Collections.Generic.List<GatherRule>(),
                 ImeLogPatterns = new System.Collections.Generic.List<ImeLogPattern>()

src/Agent/AutopilotMonitor.Agent.V2.Core/Monitoring/Enrollment/Ime/ImeLogTracker.Handlers.cs

@@ -112,7 +112,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.Ime
                     $"size={fileSize}, peers={bytesFromPeers} ({peerCachingPct}%), " +
                     $"http={bytesFromHttp}, cache={bytesFromCacheServer}, mode={downloadMode}, duration={downloadDuration}");
 
-                OnDoTelemetryReceived?.Invoke(pkg);
+                OnDoTelemetryReceived?.Invoke(pkg, LastMatchedLogTimestamp);
                 _stateDirty = true;
             }
             catch (Exception ex)

src/Agent/AutopilotMonitor.Agent.V2.Core/Monitoring/Enrollment/Ime/ImeLogTracker.LogProcessing.cs

@@ -7,6 +7,7 @@ using System.Text.RegularExpressions;
 using System.Threading;
 using System.Threading.Tasks;
 using AutopilotMonitor.Agent.V2.Core.Logging;
+using AutopilotMonitor.Shared.Logging;
 using AutopilotMonitor.Shared.Models;
 
 namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.Ime

src/Agent/AutopilotMonitor.Agent.V2.Core/Monitoring/Enrollment/Ime/ImeLogTracker.cs

@@ -194,7 +194,11 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.Ime
         public Action OnAllAppsCompleted { get; set; }
         public Action OnUserSessionCompleted { get; set; }
         public Action<string> OnImeSessionChange { get; set; }
-        public Action<AppPackageState> OnDoTelemetryReceived { get; set; }
+        // Second arg: the [DO TEL] source log line's timestamp when the DO data came from a
+        // log line, null when the DO collector observed the completion live via polling. The
+        // consumer must stamp poll-driven telemetry with the clock — inheriting an unrelated
+        // line's LastMatchedLogTimestamp put a tz-skewed time on the event (session df1fcf47).
+        public Action<AppPackageState, DateTime?> OnDoTelemetryReceived { get; set; }
         public Action<ScriptExecutionState> OnScriptCompleted { get; set; }
 
         /// <summary>

src/Agent/AutopilotMonitor.Agent.V2.Core/Monitoring/Enrollment/SystemSignals/ModernDeploymentTracker.cs

@@ -631,10 +631,15 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals
         /// the regular <see cref="ProcessRecord"/> pipeline with isBackfill=true, so they arrive
         /// as modern_deployment_error events carrying backfilled=true plus the original
         /// timeCreated; the event's own timestamp is emission time, so session StartedAt is not
-        /// dragged backwards. Newest-first, capped, watermark-deduped across restarts.
+        /// dragged backwards. The scan reads newest-first (the cap keeps the newest records),
+        /// but replay is buffered so an Info summary event announces the block BEFORE the errors
+        /// hit the timeline (customer feedback 2026-07-28: an unannounced wall of pre-agent
+        /// Error events reads like a live failure) and the records emit oldest-first, giving the
+        /// timeline sequence the original event-log chronology. Watermark-deduped across restarts.
         /// </summary>
         private void BackfillAutopilotErrors()
         {
+            var buffered = new List<EventRecord>();
             try
             {
                 long watermark;
@@ -649,7 +654,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals
                     ReverseDirection = true
                 };
 
-                int processed = 0, skippedWatermark = 0, droppedOverCap = 0;
+                int skippedWatermark = 0, droppedOverCap = 0;
                 long maxSeen = watermark;
 
                 using (var reader = new EventLogReader(query))
@@ -657,37 +662,48 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals
                     EventRecord record;
                     while ((record = reader.ReadEvent()) != null)
                     {
-                        using (record)
+                        var recordId = record.RecordId ?? 0;
+                        if (recordId > maxSeen) maxSeen = recordId;
+
+                        if (recordId != 0 && recordId <= watermark)
                         {
-                            var recordId = record.RecordId ?? 0;
-                            if (recordId > maxSeen) maxSeen = recordId;
-
-                            if (recordId != 0 && recordId <= watermark)
-                            {
-                                skippedWatermark++;
-                                continue;
-                            }
-
-                            if (processed >= ErrorBackfillMaxRecords)
-                            {
-                                droppedOverCap++;
-                                continue;
-                            }
-
-                            processed++;
-                            ProcessRecord(record, "Autopilot", AutopilotChannel, isBackfill: true);
+                            skippedWatermark++;
+                            record.Dispose();
+                            continue;
                         }
+
+                        if (buffered.Count >= ErrorBackfillMaxRecords)
+                        {
+                            droppedOverCap++;
+                            record.Dispose();
+                            continue;
+                        }
+
+                        buffered.Add(record);
                     }
                 }
 
                 if (maxSeen > watermark)
                     AdvanceAutopilotErrorWatermark(maxSeen);
 
-                if (processed == 0 && droppedOverCap == 0)
+                if (buffered.Count == 0 && droppedOverCap == 0)
+                {
                     _logger.Debug($"ModernDeployment error backfill: nothing new (skippedByWatermark={skippedWatermark})");
+                }
                 else
-                    _logger.Info($"ModernDeployment error backfill: forwarded {processed} record(s) " +
+                {
+                    EmitErrorBackfillSummary(buffered.Count, droppedOverCap);
+
+                    // Scan buffered newest-first — replay in reverse so the emitted sequence
+                    // follows the original event-log chronology.
+                    for (var i = buffered.Count - 1; i >= 0; i--)
+                    {
+                        ProcessRecord(buffered[i], "Autopilot", AutopilotChannel, isBackfill: true);
+                    }
+
+                    _logger.Info($"ModernDeployment error backfill: forwarded {buffered.Count} record(s) " +
                         $"(skippedByWatermark={skippedWatermark}, droppedOverCap={droppedOverCap})");
+                }
             }
             catch (EventLogNotFoundException)
             {
@@ -701,6 +717,49 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals
             {
                 _logger.Warning($"ModernDeployment error backfill failed: {ex.Message}");
             }
+            finally
+            {
+                foreach (var record in buffered)
+                {
+                    try { record.Dispose(); } catch { }
+                }
+            }
+        }
+
+        /// <summary>
+        /// Announces the error-backfill block on the session timeline BEFORE the replayed
+        /// errors, so pre-agent Error events are readable as history rather than a live
+        /// failure. The web timeline additionally badges each replayed event via its
+        /// backfilled=true payload marker; this summary carries backfillSummary=true instead —
+        /// it is a live emission, not a replayed record.
+        /// </summary>
+        internal void EmitErrorBackfillSummary(int replayedCount, int droppedOverCap)
+        {
+            var message = $"[Autopilot] Replaying {replayedCount} error event(s) recorded in the Autopilot event log " +
+                $"before the agent started (lookback {ErrorBackfillLookbackMinutes / 60}h). " +
+                "These predate monitoring — if enrollment progressed afterwards, they were already resolved by a retry.";
+            if (droppedOverCap > 0)
+            {
+                message += $" {droppedOverCap} older record(s) beyond the {ErrorBackfillMaxRecords}-record cap were not replayed.";
+            }
+
+            _post.Emit(new EnrollmentEvent
+            {
+                SessionId = _sessionId,
+                TenantId = _tenantId,
+                EventType = Constants.EventTypes.ModernDeploymentLog,
+                Severity = EventSeverity.Info,
+                Source = "ModernDeploymentWatcher",
+                Phase = EnrollmentPhase.Unknown,
+                Message = message,
+                Data = new Dictionary<string, object>
+                {
+                    { "backfillSummary", true },
+                    { "replayedCount", replayedCount },
+                    { "droppedOverCap", droppedOverCap },
+                    { "lookbackMinutes", ErrorBackfillLookbackMinutes }
+                }
+            });
         }
 
         /// <summary>

src/Agent/AutopilotMonitor.Agent.V2.Core/Monitoring/Enrollment/SystemSignals/StallProbeCollector.cs

@@ -10,6 +10,7 @@ using AutopilotMonitor.Agent.V2.Core.Logging;
 using AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.Ime;
 using AutopilotMonitor.Agent.V2.Core.Orchestration;
 using AutopilotMonitor.Shared;
+using AutopilotMonitor.Shared.Logging;
 using AutopilotMonitor.Shared.Models;
 using Microsoft.Win32;
 

src/Agent/AutopilotMonitor.Agent.V2.Core/Monitoring/Interop/NetshWifiFallback.cs

@@ -0,0 +1,221 @@
+using System;
+using System.Diagnostics;
+using AutopilotMonitor.Agent.V2.Core.Security;
+
+namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Interop
+{
+    /// <summary>
+    /// Fallback WiFi reader via <c>netsh wlan show interfaces</c> output parsing, used ONLY
+    /// when <see cref="WifiInfoReader"/> (native WLAN API) yields nothing on a WiFi-connected
+    /// device. Field evidence 2026-07-28: the WLAN API can return nothing in the OOBE/SYSTEM
+    /// context on builds where inbox netsh still reports the connection — until that is fully
+    /// root-caused (suspect: Wi-Fi location gating, 24H2+), netsh stays as the safety net.
+    /// <para>
+    /// netsh labels follow the OS UI language, so the parser matches the label variants of
+    /// every language implied by the enrollment geography seen to date (see the comment on
+    /// the key arrays for the country→language derivation). Unknown-language labels fall
+    /// through harmlessly — the affected field is simply absent, same as before. "SSID"
+    /// itself is untranslated in all known locales.
+    /// </para>
+    /// </summary>
+    internal static class NetshWifiFallback
+    {
+        private const int NetshTimeoutMs = 5000;
+
+        // Label variants per field, by OS UI language. Matched case-insensitively against the
+        // full text left of the colon, so acronym-suffixed keys ("AP BSSID") never collide.
+        // Language set derived from enrollment geography (get_geographic_metrics, 365d):
+        // US/GB/AU/CA/IE/SG/IN/ZA/NG/PH en · DE/AT/CH de · BE/NL nl · BE/FR/CH fr · DK da ·
+        // SE sv · PL pl · TR tr · CN zh-CN · HK zh-TW · ES/MX/PE/PY es · CZ cs · SK sk ·
+        // IT/CH it · ID id · MY ms · FI fi · LT lt · LV lv · HU hu · BR/PT pt · JP ja ·
+        // KR ko · TH th · VN vi · RO/MD ro · BG bg · BA/HR hr · AE/SA/EG/JO ar ·
+        // MN/GE/AZ usually en/ru images → ru.
+        private static readonly string[] SignalKeys =
+        {
+            "Signal",     // en, de, fr, sv, da, nb, hr
+            "Señal",      // es
+            "Sinal",      // pt
+            "Segnale",    // it
+            "Signaal",    // nl
+            "Sygnał",     // pl
+            "Signál",     // cs, sk
+            "Sinyal",     // tr, id
+            "Isyarat",    // ms
+            "Signaali",   // fi
+            "Signalas",   // lt
+            "Signāls",    // lv
+            "Jel",        // hu
+            "Semnal",     // ro
+            "Tín hiệu",   // vi
+            "สัญญาณ",     // th
+            "الإشارة",    // ar
+            "إشارة",      // ar (variant without article)
+            "Сигнал",     // ru, bg
+            "シグナル",    // ja
+            "信号",        // zh-CN
+            "訊號",        // zh-TW
+            "신호",        // ko
+        };
+
+        private static readonly string[] RadioTypeKeys =
+        {
+            "Radio type",      // en
+            "Funktyp",         // de
+            "Type de radio",   // fr
+            "Tipo de radio",   // es
+            "Tipo de rádio",   // pt
+            "Tipo di radio",   // it
+            "Radiotype",       // nl, da
+            "Radiotyp",        // sv
+            "Typ radia",       // pl
+            "Typ rádia",       // cs, sk
+            "Radyo türü",      // tr
+            "Jenis radio",     // id, ms
+            "Radiotyyppi",     // fi
+            "Radijo tipas",    // lt
+            "Radio tips",      // lv
+            "Rádió típusa",    // hu
+            "Tip radio",       // ro
+            "Vrsta radija",    // hr, bs
+            "Loại radio",      // vi
+            "ชนิดวิทยุ",        // th
+            "نوع الراديو",     // ar
+            "Тип радио",       // ru
+            "Тип на радиото",  // bg
+            "無線の種類",       // ja
+            "无线电类型",       // zh-CN
+            "無線電類型",       // zh-TW
+            "라디오 종류",      // ko
+            "무선 종류",        // ko (variant)
+        };
+
+        private static readonly string[] ChannelKeys =
+        {
+            "Channel",     // en
+            "Kanal",       // de, sv, da, nb, tr, hr
+            "Canal",       // fr, es, pt, ro
+            "Canale",      // it
+            "Kanaal",      // nl
+            "Kanał",       // pl
+            "Kanál",       // cs, sk
+            "Saluran",     // id, ms
+            "Kanava",      // fi
+            "Kanalas",     // lt
+            "Kanāls",      // lv
+            "Csatorna",    // hu
+            "Kênh",        // vi
+            "ช่องสัญญาณ",   // th
+            "ช่อง",         // th (variant)
+            "القناة",      // ar
+            "قناة",        // ar (variant without article)
+            "Канал",       // ru, bg
+            "チャネル",     // ja
+            "信道",         // zh-CN
+            "通道",         // zh-TW / zh-CN (variant)
+            "채널",         // ko
+        };
+
+        /// <summary>
+        /// Runs <c>netsh wlan show interfaces</c> and parses its output. Returns a
+        /// <see cref="WifiConnectionInfo"/> with the fields that could be parsed, or null when
+        /// nothing was found (no WLAN, netsh failure, timeout, or unrecognized localized
+        /// labels). Never throws.
+        /// </summary>
+        internal static WifiConnectionInfo TryRead()
+        {
+            try
+            {
+                var psi = new ProcessStartInfo
+                {
+                    FileName = SystemPaths.Netsh,
+                    Arguments = "wlan show interfaces",
+                    UseShellExecute = false,
+                    RedirectStandardOutput = true,
+                    RedirectStandardError = true,
+                    CreateNoWindow = true
+                };
+
+                string output;
+                using (var process = Process.Start(psi))
+                {
+                    output = process.StandardOutput.ReadToEnd();
+                    if (!process.WaitForExit(NetshTimeoutMs))
+                    {
+                        try { process.Kill(); } catch { }
+                        return null;
+                    }
+                }
+
+                return Parse(output);
+            }
+            catch
+            {
+                return null;
+            }
+        }
+
+        /// <summary>
+        /// Pure parser over the netsh output text. Internal for direct unit-testing via
+        /// InternalsVisibleTo (TryRead itself spawns a process and stays untested).
+        /// </summary>
+        internal static WifiConnectionInfo Parse(string output)
+        {
+            if (string.IsNullOrEmpty(output))
+                return null;
+
+            string ssid = null, radioType = null;
+            int? signal = null, channel = null;
+
+            foreach (var line in output.Split(new[] { '\r', '\n' }, StringSplitOptions.RemoveEmptyEntries))
+            {
+                var trimmed = line.Trim();
+                var colonIndex = trimmed.IndexOf(':');
+                if (colonIndex < 0) continue;
+
+                var key = trimmed.Substring(0, colonIndex).Trim();
+                var value = trimmed.Substring(colonIndex + 1).Trim();
+
+                if (key.Equals("SSID", StringComparison.OrdinalIgnoreCase))
+                {
+                    ssid = value;
+                }
+                else if (MatchesAny(key, SignalKeys))
+                {
+                    // Value formats seen: "94%", "94% " (trailing space), "94 %".
+                    if (int.TryParse(value.TrimEnd('%', ' '), out var sig))
+                        signal = sig;
+                }
+                else if (MatchesAny(key, RadioTypeKeys))
+                {
+                    radioType = value;
+                }
+                else if (MatchesAny(key, ChannelKeys))
+                {
+                    if (int.TryParse(value, out var ch))
+                        channel = ch;
+                }
+            }
+
+            if (ssid == null && signal == null && radioType == null && channel == null)
+                return null;
+
+            return new WifiConnectionInfo
+            {
+                Ssid = ssid,
+                SignalPercent = signal,
+                RadioType = radioType,
+                Channel = channel,
+            };
+        }
+
+        private static bool MatchesAny(string key, string[] candidates)
+        {
+            foreach (var candidate in candidates)
+            {
+                if (key.Equals(candidate, StringComparison.OrdinalIgnoreCase))
+                    return true;
+            }
+            return false;
+        }
+    }
+}

src/Agent/AutopilotMonitor.Agent.V2.Core/Monitoring/Interop/WifiInfoReader.cs

@@ -0,0 +1,234 @@
+using System;
+using System.Runtime.InteropServices;
+using System.Text;
+using static AutopilotMonitor.Agent.V2.Core.Monitoring.Interop.WlanNativeMethods;
+
+namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Interop
+{
+    /// <summary>
+    /// Current WiFi connection details as read from the native WLAN API.
+    /// </summary>
+    public sealed class WifiConnectionInfo
+    {
+        /// <summary>SSID of the connected network; null when the AP broadcasts an empty SSID.</summary>
+        public string Ssid { get; internal set; }
+
+        /// <summary>
+        /// Signal quality 0–100 (same semantics as the netsh "Signal" percentage). Always set
+        /// on the native WLAN API path; null only when the netsh fallback could not parse it.
+        /// </summary>
+        public int? SignalPercent { get; internal set; }
+
+        /// <summary>Human-readable PHY generation ("802.11ax" …); null for exotic/unknown PHYs.</summary>
+        public string RadioType { get; internal set; }
+
+        /// <summary>Current 802.11 channel number; null when the channel query fails.</summary>
+        public int? Channel { get; internal set; }
+    }
+
+    /// <summary>
+    /// Fail-soft reader over <see cref="WlanNativeMethods"/>: returns the current WiFi
+    /// connection or null — never throws, never blocks on a child process. Machines without
+    /// the WLAN AutoConfig service (VMs, wired-only devices) simply return null.
+    /// </summary>
+    public static class WifiInfoReader
+    {
+        /// <summary>
+        /// Reads the current WiFi connection. When <paramref name="preferredInterfaceId"/> is
+        /// given (the adapter GUID from <c>NetworkInterface.Id</c>), that interface is queried
+        /// first; otherwise — or when it is not connected — the first connected WLAN interface
+        /// wins. Returns null when no interface has an active connection.
+        /// </summary>
+        public static WifiConnectionInfo TryGetCurrentConnection(Guid? preferredInterfaceId = null)
+            => TryGetCurrentConnection(preferredInterfaceId, out _);
+
+        /// <summary>
+        /// Same as <see cref="TryGetCurrentConnection(Guid?)"/> but reports WHY the read
+        /// yielded nothing via <paramref name="diagnostics"/> (native return codes per step).
+        /// The WLAN API can fail in ways that are invisible from the outside (e.g. per-process
+        /// access gating on newer Windows builds) — callers log this at Debug so field issues
+        /// are explainable from the agent log instead of a silent missing event.
+        /// </summary>
+        public static WifiConnectionInfo TryGetCurrentConnection(Guid? preferredInterfaceId, out string diagnostics)
+        {
+            var diag = new StringBuilder();
+            var clientHandle = IntPtr.Zero;
+            try
+            {
+                var rc = WlanOpenHandle(WLAN_CLIENT_VERSION, IntPtr.Zero, out _, out clientHandle);
+                if (rc != ERROR_SUCCESS)
+                {
+                    diagnostics = $"WlanOpenHandle rc={rc}";
+                    return null;
+                }
+
+                var interfaceList = IntPtr.Zero;
+                try
+                {
+                    rc = WlanEnumInterfaces(clientHandle, IntPtr.Zero, out interfaceList);
+                    if (rc != ERROR_SUCCESS)
+                    {
+                        diagnostics = $"WlanEnumInterfaces rc={rc}";
+                        return null;
+                    }
+
+                    var count = (uint)Marshal.ReadInt32(interfaceList);
+                    if (count == 0)
+                    {
+                        diagnostics = "no WLAN interfaces";
+                        return null;
+                    }
+
+                    var infoSize = Marshal.SizeOf(typeof(WLAN_INTERFACE_INFO));
+                    // List header: DWORD dwNumberOfItems + DWORD dwIndex, then the info array.
+                    var firstEntry = new IntPtr(interfaceList.ToInt64() + 8);
+
+                    WifiConnectionInfo fallback = null;
+                    for (var i = 0; i < count; i++)
+                    {
+                        var entryPtr = new IntPtr(firstEntry.ToInt64() + i * infoSize);
+                        var info = (WLAN_INTERFACE_INFO)Marshal.PtrToStructure(entryPtr, typeof(WLAN_INTERFACE_INFO));
+
+                        var connection = QueryCurrentConnection(clientHandle, info.InterfaceGuid, diag);
+                        if (connection == null)
+                            continue;
+
+                        if (preferredInterfaceId.HasValue && info.InterfaceGuid == preferredInterfaceId.Value)
+                        {
+                            diagnostics = null;
+                            return connection;
+                        }
+
+                        if (fallback == null)
+                            fallback = connection;
+                    }
+
+                    diagnostics = fallback == null ? diag.ToString() : null;
+                    return fallback;
+                }
+                finally
+                {
+                    if (interfaceList != IntPtr.Zero)
+                        WlanFreeMemory(interfaceList);
+                }
+            }
+            catch (Exception ex)
+            {
+                diagnostics = $"exception {ex.GetType().Name}: {ex.Message}";
+                return null;
+            }
+            finally
+            {
+                if (clientHandle != IntPtr.Zero)
+                    WlanCloseHandle(clientHandle, IntPtr.Zero);
+            }
+        }
+
+        private static WifiConnectionInfo QueryCurrentConnection(IntPtr clientHandle, Guid interfaceGuid, StringBuilder diag)
+        {
+            var dataPtr = IntPtr.Zero;
+            try
+            {
+                var rc = WlanQueryInterface(clientHandle, ref interfaceGuid,
+                        WLAN_INTF_OPCODE.wlan_intf_opcode_current_connection,
+                        IntPtr.Zero, out _, out dataPtr, IntPtr.Zero);
+                if (rc != ERROR_SUCCESS)
+                {
+                    diag.Append($"[{interfaceGuid:D}] query(current_connection) rc={rc}; ");
+                    return null;
+                }
+
+                var attributes = (WLAN_CONNECTION_ATTRIBUTES)Marshal.PtrToStructure(
+                    dataPtr, typeof(WLAN_CONNECTION_ATTRIBUTES));
+
+                if (attributes.isState != WLAN_INTERFACE_STATE.wlan_interface_state_connected)
+                {
+                    diag.Append($"[{interfaceGuid:D}] state={attributes.isState}; ");
+                    return null;
+                }
+
+                var assoc = attributes.wlanAssociationAttributes;
+                return new WifiConnectionInfo
+                {
+                    Ssid = DecodeSsid(assoc.dot11Ssid.ucSSID, assoc.dot11Ssid.uSSIDLength),
+                    SignalPercent = (int)Math.Min(assoc.wlanSignalQuality, 100),
+                    RadioType = PhyTypeToRadioType(assoc.dot11PhyType),
+                    Channel = QueryChannel(clientHandle, interfaceGuid),
+                };
+            }
+            finally
+            {
+                if (dataPtr != IntPtr.Zero)
+                    WlanFreeMemory(dataPtr);
+            }
+        }
+
+        private static int? QueryChannel(IntPtr clientHandle, Guid interfaceGuid)
+        {
+            var dataPtr = IntPtr.Zero;
+            try
+            {
+                if (WlanQueryInterface(clientHandle, ref interfaceGuid,
+                        WLAN_INTF_OPCODE.wlan_intf_opcode_channel_number,
+                        IntPtr.Zero, out var dataSize, out dataPtr, IntPtr.Zero) != ERROR_SUCCESS)
+                    return null;
+
+                if (dataSize < sizeof(uint) || dataPtr == IntPtr.Zero)
+                    return null;
+
+                return Marshal.ReadInt32(dataPtr);
+            }
+            catch
+            {
+                return null;
+            }
+            finally
+            {
+                if (dataPtr != IntPtr.Zero)
+                    WlanFreeMemory(dataPtr);
+            }
+        }
+
+        /// <summary>
+        /// Decodes a raw DOT11_SSID (UTF-8 by convention) into a string; null for empty SSIDs.
+        /// Internal for direct unit-testing via InternalsVisibleTo.
+        /// </summary>
+        internal static string DecodeSsid(byte[] raw, uint length)
+        {
+            if (raw == null || length == 0)
+                return null;
+
+            var byteCount = (int)Math.Min(length, (uint)raw.Length);
+            try
+            {
+                var ssid = Encoding.UTF8.GetString(raw, 0, byteCount);
+                return string.IsNullOrEmpty(ssid) ? null : ssid;
+            }
+            catch
+            {
+                return null;
+            }
+        }
+
+        /// <summary>
+        /// Maps a DOT11 PHY type to the same strings netsh historically reported as
+        /// "Radio type" — keeps event payloads consistent across the netsh→WLAN-API switch.
+        /// Internal for direct unit-testing via InternalsVisibleTo.
+        /// </summary>
+        internal static string PhyTypeToRadioType(DOT11_PHY_TYPE phyType)
+        {
+            switch (phyType)
+            {
+                case DOT11_PHY_TYPE.dot11_phy_type_ofdm: return "802.11a";
+                case DOT11_PHY_TYPE.dot11_phy_type_hrdsss: return "802.11b";
+                case DOT11_PHY_TYPE.dot11_phy_type_erp: return "802.11g";
+                case DOT11_PHY_TYPE.dot11_phy_type_ht: return "802.11n";
+                case DOT11_PHY_TYPE.dot11_phy_type_vht: return "802.11ac";
+                case DOT11_PHY_TYPE.dot11_phy_type_dmg: return "802.11ad";
+                case DOT11_PHY_TYPE.dot11_phy_type_he: return "802.11ax";
+                case DOT11_PHY_TYPE.dot11_phy_type_eht: return "802.11be";
+                default: return null;
+            }
+        }
+    }
+}

src/Agent/AutopilotMonitor.Agent.V2.Core/Monitoring/Interop/WlanNativeMethods.cs

@@ -0,0 +1,142 @@
+using System;
+using System.Runtime.InteropServices;
+
+namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Interop
+{
+    /// <summary>
+    /// Native WLAN API interop (<c>wlanapi.dll</c>) used to read the current WiFi connection
+    /// (SSID, signal quality, PHY type, channel) without spawning <c>netsh</c>.
+    /// <para>
+    /// The WLAN API is language-neutral — unlike parsing <c>netsh wlan show interfaces</c>
+    /// output, whose labels follow the OS UI language and silently drop fields on
+    /// non-English images. On machines without the WLAN AutoConfig service (VMs, servers,
+    /// wired-only devices) <c>WlanOpenHandle</c>/<c>WlanEnumInterfaces</c> fail with a
+    /// non-zero error code; callers treat that as "no WiFi" (see <see cref="WifiInfoReader"/>).
+    /// </para>
+    /// </summary>
+    internal static class WlanNativeMethods
+    {
+        internal const uint ERROR_SUCCESS = 0;
+
+        /// <summary>Client version 2 = Vista and later (the only relevant range).</summary>
+        internal const uint WLAN_CLIENT_VERSION = 2;
+
+        internal enum WLAN_INTF_OPCODE : uint
+        {
+            wlan_intf_opcode_current_connection = 7,
+            wlan_intf_opcode_channel_number = 8,
+        }
+
+        internal enum WLAN_INTERFACE_STATE
+        {
+            wlan_interface_state_not_ready = 0,
+            wlan_interface_state_connected = 1,
+            wlan_interface_state_ad_hoc_network_formed = 2,
+            wlan_interface_state_disconnecting = 3,
+            wlan_interface_state_disconnected = 4,
+            wlan_interface_state_associating = 5,
+            wlan_interface_state_discovering = 6,
+            wlan_interface_state_authenticating = 7,
+        }
+
+        internal enum DOT11_PHY_TYPE : uint
+        {
+            dot11_phy_type_unknown = 0,
+            dot11_phy_type_fhss = 1,
+            dot11_phy_type_dsss = 2,
+            dot11_phy_type_irbaseband = 3,
+            dot11_phy_type_ofdm = 4,    // 802.11a
+            dot11_phy_type_hrdsss = 5,  // 802.11b
+            dot11_phy_type_erp = 6,     // 802.11g
+            dot11_phy_type_ht = 7,      // 802.11n
+            dot11_phy_type_vht = 8,     // 802.11ac
+            dot11_phy_type_dmg = 9,     // 802.11ad
+            dot11_phy_type_he = 10,     // 802.11ax
+            dot11_phy_type_eht = 11,    // 802.11be
+        }
+
+        [StructLayout(LayoutKind.Sequential, CharSet = CharSet.Unicode)]
+        internal struct WLAN_INTERFACE_INFO
+        {
+            public Guid InterfaceGuid;
+            [MarshalAs(UnmanagedType.ByValTStr, SizeConst = 256)]
+            public string strInterfaceDescription;
+            public WLAN_INTERFACE_STATE isState;
+        }
+
+        [StructLayout(LayoutKind.Sequential)]
+        internal struct DOT11_SSID
+        {
+            public uint uSSIDLength;
+            [MarshalAs(UnmanagedType.ByValArray, SizeConst = 32)]
+            public byte[] ucSSID;
+        }
+
+        [StructLayout(LayoutKind.Sequential)]
+        internal struct WLAN_ASSOCIATION_ATTRIBUTES
+        {
+            public DOT11_SSID dot11Ssid;
+            public int dot11BssType;
+            [MarshalAs(UnmanagedType.ByValArray, SizeConst = 6)]
+            public byte[] dot11Bssid;
+            public DOT11_PHY_TYPE dot11PhyType;
+            public uint uDot11PhyIndex;
+            public uint wlanSignalQuality; // 0..100, same semantics as netsh "Signal"
+            public uint ulRxRate;
+            public uint ulTxRate;
+        }
+
+        [StructLayout(LayoutKind.Sequential)]
+        internal struct WLAN_SECURITY_ATTRIBUTES
+        {
+            [MarshalAs(UnmanagedType.Bool)]
+            public bool bSecurityEnabled;
+            [MarshalAs(UnmanagedType.Bool)]
+            public bool bOneXEnabled;
+            public int dot11AuthAlgorithm;
+            public int dot11CipherAlgorithm;
+        }
+
+        [StructLayout(LayoutKind.Sequential, CharSet = CharSet.Unicode)]
+        internal struct WLAN_CONNECTION_ATTRIBUTES
+        {
+            public WLAN_INTERFACE_STATE isState;
+            public int wlanConnectionMode;
+            [MarshalAs(UnmanagedType.ByValTStr, SizeConst = 256)]
+            public string strProfileName;
+            public WLAN_ASSOCIATION_ATTRIBUTES wlanAssociationAttributes;
+            public WLAN_SECURITY_ATTRIBUTES wlanSecurityAttributes;
+        }
+
+        [DllImport("wlanapi.dll")]
+        internal static extern uint WlanOpenHandle(
+            uint dwClientVersion,
+            IntPtr pReserved,
+            out uint pdwNegotiatedVersion,
+            out IntPtr phClientHandle);
+
+        [DllImport("wlanapi.dll")]
+        internal static extern uint WlanCloseHandle(
+            IntPtr hClientHandle,
+            IntPtr pReserved);
+
+        [DllImport("wlanapi.dll")]
+        internal static extern uint WlanEnumInterfaces(
+            IntPtr hClientHandle,
+            IntPtr pReserved,
+            out IntPtr ppInterfaceList);
+
+        [DllImport("wlanapi.dll")]
+        internal static extern uint WlanQueryInterface(
+            IntPtr hClientHandle,
+            [In] ref Guid pInterfaceGuid,
+            WLAN_INTF_OPCODE OpCode,
+            IntPtr pReserved,
+            out uint pdwDataSize,
+            out IntPtr ppData,
+            IntPtr pWlanOpcodeValueType);
+
+        [DllImport("wlanapi.dll")]
+        internal static extern void WlanFreeMemory(IntPtr pMemory);
+    }
+}

src/Agent/AutopilotMonitor.Agent.V2.Core/Monitoring/Runtime/DiagnosticsPackageService.cs

@@ -218,15 +218,18 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Runtime
         /// This method is non-fatal: all exceptions are caught and logged.
         /// </summary>
         /// <param name="enrollmentSucceeded">
-        /// True for a successful enrollment (affects OnFailure mode check and sessioninfo.txt content).
-        /// Pass true for WhiteGlove pre-provisioning (it succeeded up to this point).
+        /// True for a successful enrollment, false for a failed one (drives the OnFailure mode
+        /// check and sessioninfo.txt content). Pass true for WhiteGlove pre-provisioning (it
+        /// succeeded up to this point). Pass <b>null</b> when the session has no outcome yet
+        /// (on-demand server-requested collection mid-enrollment): the OnFailure gate does not
+        /// apply — there is no success to skip on — and sessioninfo.txt records "In Progress".
         /// </param>
         /// <param name="fileNameSuffix">
         /// Optional suffix inserted before the .zip extension.
         /// Example: "preprov" → AgentDiagnostics-{sessionId}-{timestamp}-preprov.zip
         /// Null (default) → AgentDiagnostics-{sessionId}-{timestamp}.zip
         /// </param>
-        public virtual async Task<DiagnosticsUploadResult> CreateAndUploadAsync(bool enrollmentSucceeded, string fileNameSuffix = null)
+        public virtual async Task<DiagnosticsUploadResult> CreateAndUploadAsync(bool? enrollmentSucceeded, string fileNameSuffix = null)
         {
             try
             {
@@ -244,13 +247,15 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Runtime
                     return null;
                 }
 
-                if (string.Equals(mode, "OnFailure", StringComparison.OrdinalIgnoreCase) && enrollmentSucceeded)
+                // Null outcome (on-demand mid-session) passes through: the OnFailure gate only
+                // skips a KNOWN success — an in-flight session has nothing to skip on.
+                if (string.Equals(mode, "OnFailure", StringComparison.OrdinalIgnoreCase) && enrollmentSucceeded == true)
                 {
                     _logger.Info("Diagnostics upload skipped: enrollment succeeded and mode=OnFailure");
                     return null;
                 }
 
-                _logger.Info($"Creating diagnostics package (mode={mode}, enrollmentSucceeded={enrollmentSucceeded}{(fileNameSuffix != null ? $", suffix={fileNameSuffix}" : "")})...");
+                _logger.Info($"Creating diagnostics package (mode={mode}, enrollmentSucceeded={(enrollmentSucceeded.HasValue ? enrollmentSucceeded.ToString() : "n/a")}{(fileNameSuffix != null ? $", suffix={fileNameSuffix}" : "")})...");
 
                 // Build ZIP in memory
                 var timestamp = DateTime.UtcNow.ToString("yyyyMMddHHmmss");
@@ -343,7 +348,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Runtime
 
         // Builds the diagnostics ZIP body in-memory. Extracted from CreateAndUploadAsync so
         // tests can assert archive contents without going through the upload path.
-        internal virtual byte[] BuildArchiveBytes(bool enrollmentSucceeded)
+        internal virtual byte[] BuildArchiveBytes(bool? enrollmentSucceeded)
         {
             var tracker = new BudgetTracker(Budget);
             using (var ms = new MemoryStream())
@@ -414,14 +419,14 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Runtime
             }
         }
 
-        private void AddSessionInfo(ZipArchive archive, bool enrollmentSucceeded)
+        private void AddSessionInfo(ZipArchive archive, bool? enrollmentSucceeded)
         {
             var sb = new StringBuilder();
             sb.AppendLine($"Session ID: {_configuration.SessionId}");
             sb.AppendLine($"Tenant ID: {_configuration.TenantId}");
             sb.AppendLine($"Device Name: {Environment.MachineName}");
             sb.AppendLine($"Timestamp: {DateTime.UtcNow:O}");
-            sb.AppendLine($"Enrollment Result: {(enrollmentSucceeded ? "Succeeded" : "Failed")}");
+            sb.AppendLine($"Enrollment Result: {(enrollmentSucceeded == null ? "In Progress" : enrollmentSucceeded.Value ? "Succeeded" : "Failed")}");
 
             // Hardware info via existing DeviceInfoProvider (WMI)
             sb.AppendLine($"Manufacturer: {DeviceInfoProvider.GetManufacturer()}");

src/Agent/AutopilotMonitor.Agent.V2.Core/Monitoring/Telemetry/DeviceInfo/DeviceInfoCollector.NetworkAndSecurity.cs

@@ -815,7 +815,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.DeviceInfo
         /// Collects active network interface details (name, type, link speed, MAC) using
         /// System.Net.NetworkInformation — instant, no process spawn.
         /// If the active interface is WiFi, fires off a separate async task to collect
-        /// WiFi signal info via netsh (fire-and-forget, never blocks).
+        /// WiFi signal info via the native WLAN API (fire-and-forget, never blocks).
         /// </summary>
         private void CollectActiveNetworkInterfaceInfo()
         {
@@ -858,7 +858,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.DeviceInfo
                 // Fire-and-forget WiFi signal collection — separate event, never blocks
                 if (isWifi)
                 {
-                    Task.Run(() => CollectWiFiSignalInfo());
+                    Guid? nicGuid = Guid.TryParse(activeNic.Id, out var parsedGuid) ? parsedGuid : (Guid?)null;
+                    Task.Run(() => CollectWiFiSignalInfo(nicGuid));
                 }
             }
             catch (Exception ex)
@@ -899,78 +900,41 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.DeviceInfo
         }
 
         /// <summary>
-        /// Collects WiFi signal info via netsh wlan show interfaces and emits a separate
-        /// wifi_signal_info event. Designed to run as fire-and-forget via Task.Run —
-        /// never blocks other collection. VMs without WiFi service simply get no event.
+        /// Collects WiFi signal info via the native WLAN API (<see cref="WifiInfoReader"/>,
+        /// language-neutral, no process spawn) and emits a separate wifi_signal_info event.
+        /// Designed to run as fire-and-forget via Task.Run — never blocks other collection.
+        /// VMs without WiFi service simply get no event.
         /// </summary>
-        private void CollectWiFiSignalInfo()
+        private void CollectWiFiSignalInfo(Guid? interfaceGuid)
         {
             try
             {
-                var psi = new ProcessStartInfo
+                var wifi = WifiInfoReader.TryGetCurrentConnection(interfaceGuid, out var wifiDiag);
+                if (wifi == null)
                 {
-                    FileName = SystemPaths.Netsh,
-                    Arguments = "wlan show interfaces",
-                    UseShellExecute = false,
-                    RedirectStandardOutput = true,
-                    RedirectStandardError = true,
-                    CreateNoWindow = true
-                };
-
-                string output;
-                using (var process = Process.Start(psi))
-                {
-                    output = process.StandardOutput.ReadToEnd();
-                    process.WaitForExit(5000);
+                    _logger.Debug($"EnrollmentTracker: native WLAN API returned no WiFi info ({wifiDiag ?? "no connected WLAN interface"}) — trying netsh fallback");
+                    wifi = NetshWifiFallback.TryRead();
+                    if (wifi == null)
+                        return;
                 }
 
-                if (string.IsNullOrEmpty(output))
-                    return;
-
                 var data = new Dictionary<string, object>();
+                if (wifi.Ssid != null)
+                    data["wifiSsid"] = wifi.Ssid;
+                if (wifi.SignalPercent.HasValue)
+                    data["wifiSignalPercent"] = wifi.SignalPercent.Value;
+                if (wifi.RadioType != null)
+                    data["wifiRadioType"] = wifi.RadioType;
+                if (wifi.Channel.HasValue)
+                    data["wifiChannel"] = wifi.Channel.Value;
 
-                foreach (var line in output.Split(new[] { '\r', '\n' }, StringSplitOptions.RemoveEmptyEntries))
-                {
-                    var trimmed = line.Trim();
-                    var colonIndex = trimmed.IndexOf(':');
-                    if (colonIndex < 0) continue;
+                var message = wifi.Ssid != null ? $"WiFi: {wifi.Ssid}" : "WiFi signal info";
+                if (wifi.SignalPercent.HasValue)
+                    message += $", Signal: {wifi.SignalPercent.Value}%";
+                if (wifi.RadioType != null)
+                    message += $" ({wifi.RadioType})";
 
-                    var key = trimmed.Substring(0, colonIndex).Trim();
-                    var value = trimmed.Substring(colonIndex + 1).Trim();
-
-                    if (key.Equals("SSID", StringComparison.OrdinalIgnoreCase) &&
-                        !key.Equals("BSSID", StringComparison.OrdinalIgnoreCase))
-                    {
-                        data["wifiSsid"] = value;
-                    }
-                    else if (key.Equals("Signal", StringComparison.OrdinalIgnoreCase))
-                    {
-                        if (int.TryParse(value.TrimEnd('%'), out var signal))
-                            data["wifiSignalPercent"] = signal;
-                    }
-                    else if (key.Equals("Radio type", StringComparison.OrdinalIgnoreCase))
-                    {
-                        data["wifiRadioType"] = value;
-                    }
-                    else if (key.Equals("Channel", StringComparison.OrdinalIgnoreCase))
-                    {
-                        if (int.TryParse(value, out var channel))
-                            data["wifiChannel"] = channel;
-                    }
-                }
-
-                if (data.Count > 0)
-                {
-                    var message = data.ContainsKey("wifiSsid")
-                        ? $"WiFi: {data["wifiSsid"]}"
-                        : "WiFi signal info";
-                    if (data.ContainsKey("wifiSignalPercent"))
-                        message += $", Signal: {data["wifiSignalPercent"]}%";
-                    if (data.ContainsKey("wifiRadioType"))
-                        message += $" ({data["wifiRadioType"]})";
-
-                    EmitDeviceInfoEvent(Constants.EventTypes.WifiSignalInfo, message, data);
-                }
+                EmitDeviceInfoEvent(Constants.EventTypes.WifiSignalInfo, message, data);
             }
             catch (Exception ex)
             {

src/Agent/AutopilotMonitor.Agent.V2.Core/Monitoring/Telemetry/Gather/Collectors/LogParserCollector.cs

@@ -10,6 +10,7 @@ using AutopilotMonitor.Agent.V2.Core.Monitoring.Runtime;
 using AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment;
 using AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.Ime;
 using AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.SystemSignals;
+using AutopilotMonitor.Shared.Logging;
 
 namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather.Collectors
 {
@@ -25,14 +26,21 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather.Collectors
         {
             var filePath = rule.Target;
             if (string.IsNullOrEmpty(filePath))
+            {
+                context.DebugLog(rule.RuleId, GatherRuleDebugLog.StageLogParser, "empty target — nothing to parse");
                 return null;
+            }
 
             // Expand custom tokens (%LOGGED_ON_USER_PROFILE%) and standard environment variables
             var userProfilePath = UserProfileResolver.ContainsUserProfileToken(filePath)
                 ? UserProfileResolver.GetLoggedOnUserProfilePath() : null;
             filePath = UserProfileResolver.ExpandCustomTokens(filePath);
             if (filePath == null)
+            {
+                context.DebugLog(rule.RuleId, GatherRuleDebugLog.StageLogParser,
+                    "target contains %LOGGED_ON_USER_PROFILE% but no user is logged on — skipped this run");
                 return null; // Token present but no user logged on — skip silently
+            }
 
             // Apply IME log path override if set. The override comes from the local
             // --ime-log-path flag only (never from remote config), so the operator
@@ -66,6 +74,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather.Collectors
                 string.IsNullOrEmpty(patternStr))
             {
                 context.Logger.Warning($"LogParser rule {rule.RuleId} has no 'pattern' parameter");
+                context.DebugLog(rule.RuleId, GatherRuleDebugLog.StageError,
+                    "missing 'pattern' parameter — rule can never match");
                 return null;
             }
 
@@ -93,6 +103,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather.Collectors
             catch (Exception ex)
             {
                 context.Logger.Warning($"LogParser rule {rule.RuleId} has invalid regex: {ex.Message}");
+                context.DebugLog(rule.RuleId, GatherRuleDebugLog.StageError,
+                    $"invalid regex pattern '{patternStr}' — rule can never match: {ex.Message}");
                 return null;
             }
 
@@ -101,6 +113,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather.Collectors
             if (resolvedPaths.Count == 0)
             {
                 context.Logger.Debug($"LogParser rule {rule.RuleId}: no files found for: {filePath}");
+                context.DebugLog(rule.RuleId, GatherRuleDebugLog.StageLogParser,
+                    $"no files matched target {filePath}" + (HasWildcard(Path.GetFileName(filePath)) ? " (wildcard)" : "") + " — nothing to parse");
                 return null;
             }
 
@@ -120,6 +134,44 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather.Collectors
             return null;
         }
 
+        // Per-match trace lines are capped per file per run — the per-file summary line
+        // still carries the full match count, this only bounds the per-match detail.
+        private const int MaxTracedMatchesPerFile = 10;
+
+        /// <summary>
+        /// Writes one debug-trace line per regex match: the line number, the matched text,
+        /// and every capture group that will land in the emitted event (same "0" exclusion
+        /// as the event data). Stops after <see cref="MaxTracedMatchesPerFile"/> matches.
+        /// </summary>
+        private static void TraceMatch(GatherRuleContext context, GatherRule rule, string fileName,
+            int lineNumber, Match match, Regex pattern, int matchNumber)
+        {
+            if (matchNumber > MaxTracedMatchesPerFile)
+            {
+                if (matchNumber == MaxTracedMatchesPerFile + 1)
+                    context.DebugLog(rule.RuleId, GatherRuleDebugLog.StageLogParser,
+                        $"{fileName}: further matches not traced individually (cap {MaxTracedMatchesPerFile}/file/run) — see the per-file summary for the total");
+                return;
+            }
+
+            var sb = new StringBuilder();
+            sb.Append(fileName).Append(": line ").Append(lineNumber)
+              .Append(" matched \"").Append(TruncateMessage(match.Value, 200)).Append('"');
+
+            var first = true;
+            foreach (var groupName in pattern.GetGroupNames())
+            {
+                if (groupName == "0") continue;
+                var group = match.Groups[groupName];
+                if (!group.Success) continue;
+                sb.Append(first ? " — groups: " : ", ");
+                first = false;
+                sb.Append(groupName).Append("=\"").Append(TruncateMessage(group.Value, 100)).Append('"');
+            }
+
+            context.DebugLog(rule.RuleId, GatherRuleDebugLog.StageLogParser, sb.ToString());
+        }
+
         private static bool HasWildcard(string fileNamePart)
             => !string.IsNullOrEmpty(fileNamePart) &&
                (fileNamePart.Contains("*") || fileNamePart.Contains("?"));
@@ -144,7 +196,11 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather.Collectors
             try
             {
                 // Return matched files sorted by last write time (newest first), capped at 20
-                return Directory.GetFiles(directory, fileNamePart)
+                var allMatches = Directory.GetFiles(directory, fileNamePart);
+                if (allMatches.Length > 20)
+                    context.DebugLog(ruleId, GatherRuleDebugLog.StageLogParser,
+                        $"wildcard matched {allMatches.Length} files — capped to the 20 newest");
+                return allMatches
                     .OrderByDescending(f => new FileInfo(f).LastWriteTimeUtc)
                     .Take(20)
                     .ToList();
@@ -152,6 +208,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather.Collectors
             catch (Exception ex)
             {
                 context.Logger.Warning($"LogParser rule {ruleId}: wildcard expansion failed for {filePath}: {ex.Message}");
+                context.DebugLog(ruleId, GatherRuleDebugLog.StageError, $"wildcard expansion failed for {filePath}: {ex.Message}");
                 return new List<string>();
             }
         }
@@ -168,10 +225,16 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather.Collectors
 
                 // Nothing new to read
                 if (startPosition >= fileInfo.Length)
+                {
+                    context.DebugLog(rule.RuleId, GatherRuleDebugLog.StageLogParser,
+                        $"{Path.GetFileName(filePath)}: no new content (position {startPosition} >= length {fileInfo.Length}) — trackPosition=true, nothing re-read");
                     return;
+                }
 
                 int matchCount = 0;
                 int linesRead = 0;
+                int parseFailCount = 0;
+                int timeoutCount = 0;
                 long endPosition = startPosition;
 
                 using (var stream = new FileStream(filePath, FileMode.Open, FileAccess.Read, FileShare.ReadWrite))
@@ -195,6 +258,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather.Collectors
                                 }
                                 catch (RegexMatchTimeoutException)
                                 {
+                                    timeoutCount++;
                                     continue;
                                 }
                                 if (!match.Success)
@@ -233,13 +297,17 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather.Collectors
                                 });
 
                                 matchCount++;
+                                TraceMatch(context, rule, Path.GetFileName(filePath), linesRead, match, pattern, matchCount);
                             }
                             else
                             {
                                 // CMTrace mode: parse line as CMTrace format, match regex against message
                                 CmTraceLogEntry entry;
                                 if (!CmTraceLogParser.TryParseLine(line, out entry))
+                                {
+                                    parseFailCount++;
                                     continue;
+                                }
 
                                 Match match;
                                 try
@@ -248,6 +316,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather.Collectors
                                 }
                                 catch (RegexMatchTimeoutException)
                                 {
+                                    timeoutCount++;
                                     continue;
                                 }
                                 if (!match.Success)
@@ -288,6 +357,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather.Collectors
                                 });
 
                                 matchCount++;
+                                TraceMatch(context, rule, Path.GetFileName(filePath), linesRead, match, pattern, matchCount);
                             }
                         }
 
@@ -301,10 +371,24 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather.Collectors
 
                 if (matchCount > 0)
                     context.Logger.Debug($"LogParser rule {rule.RuleId}: {matchCount} matches from {linesRead} lines in {Path.GetFileName(filePath)}");
+
+                // Per-file outcome — always written so a "matched 0" run is visible too.
+                context.DebugLog(rule.RuleId, GatherRuleDebugLog.StageLogParser,
+                    $"{Path.GetFileName(filePath)}: read {linesRead} lines from position {startPosition}->{endPosition}, " +
+                    $"matched {matchCount}, parseFailures={parseFailCount}, regexTimeouts={timeoutCount}, mode={(isTextMode ? "text" : "cmtrace")}");
+
+                if (!isTextMode && linesRead > 0 && parseFailCount == linesRead)
+                    context.DebugLog(rule.RuleId, GatherRuleDebugLog.StageLogParser,
+                        "every line failed CMTrace parsing — if this is a plain-text log, set parameter format=text");
+
+                if (linesRead == maxLines)
+                    context.DebugLog(rule.RuleId, GatherRuleDebugLog.StageLogParser,
+                        $"stopped at maxLines={maxLines} — remaining content is deferred to the next run");
             }
             catch (Exception ex)
             {
                 context.Logger.Warning($"LogParser rule {rule.RuleId} failed reading {filePath}: {ex.Message}");
+                context.DebugLog(rule.RuleId, GatherRuleDebugLog.StageError, $"failed reading {filePath}: {ex}");
             }
         }
 

src/Agent/AutopilotMonitor.Agent.V2.Core/Monitoring/Telemetry/Gather/Collectors/RegistryCollector.cs

@@ -113,7 +113,11 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather.Collectors
 
                         // Suppress the "not found" event when the rule only wants a positive signal.
                         if (emitOnlyIfExists)
+                        {
+                            context.DebugLog(rule.RuleId, GatherRuleDebugLog.StageCollector,
+                                $"registry key/value not found: {path} — emitOnlyIfExists=true, empty result");
                             return new Dictionary<string, object>(); // empty → executor emits nothing
+                        }
 
                         data["exists"] = false;
                         data["path"] = path;

src/Agent/AutopilotMonitor.Agent.V2.Core/Monitoring/Telemetry/Gather/GatherRuleContext.cs

@@ -22,13 +22,20 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather
         public LogFilePositionTracker FilePositionTracker { get; }
         public bool UnrestrictedMode { get; set; }
 
+        /// <summary>
+        /// Optional gather-rule debug trace writer (EnableGatherRuleDebugLog). Null when
+        /// tracing is disabled — use <see cref="DebugLog"/> for null-safe writes.
+        /// </summary>
+        public GatherRuleDebugLog DebugWriter { get; }
+
         public GatherRuleContext(
             AgentLogger logger,
             string sessionId,
             string tenantId,
             Action<EnrollmentEvent> onEventCollected,
             string imeLogPathOverride,
-            LogFilePositionTracker filePositionTracker)
+            LogFilePositionTracker filePositionTracker,
+            GatherRuleDebugLog debugLog = null)
         {
             Logger = logger ?? throw new ArgumentNullException(nameof(logger));
             SessionId = sessionId ?? throw new ArgumentNullException(nameof(sessionId));
@@ -36,8 +43,14 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather
             OnEventCollected = onEventCollected ?? throw new ArgumentNullException(nameof(onEventCollected));
             ImeLogPathOverride = imeLogPathOverride;
             FilePositionTracker = filePositionTracker ?? throw new ArgumentNullException(nameof(filePositionTracker));
+            DebugWriter = debugLog;
         }
 
+        /// <summary>
+        /// Null-safe write to the gather-rule debug trace. No-op when tracing is disabled.
+        /// </summary>
+        public void DebugLog(string ruleId, string stage, string message) => DebugWriter?.Write(ruleId, stage, message);
+
         /// <summary>
         /// Emits a security_warning event and returns an empty result dictionary.
         /// Called when a gather rule targets a path/query not on the allowlist.
@@ -45,6 +58,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather
         public Dictionary<string, object> EmitSecurityWarning(GatherRule rule, string collectorType, string target)
         {
             Logger.Warning($"SECURITY: {collectorType} path blocked by guard: {target} (Rule: {rule.RuleId})");
+            DebugLog(rule.RuleId, GatherRuleDebugLog.StageGuard,
+                $"{collectorType} target blocked by allowlist guard: {target} — security_warning emitted, rule produced no data");
 
             var data = new Dictionary<string, object>
             {

src/Agent/AutopilotMonitor.Agent.V2.Core/Monitoring/Telemetry/Gather/GatherRuleDebugLog.cs

@@ -0,0 +1,116 @@
+using System;
+using System.IO;
+using AutopilotMonitor.Agent.V2.Core.Logging;
+
+namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather
+{
+    /// <summary>
+    /// Append-only trace file for gather-rule evaluation, enabled per tenant via
+    /// EnableGatherRuleDebugLog (or --gather-debug-log). Explains every evaluation
+    /// decision — including the outcomes that produce no event — so customers can
+    /// diagnose rules that never show up in the timeline. Every write failure is
+    /// swallowed: tracing must never break gathering.
+    /// </summary>
+    public sealed class GatherRuleDebugLog
+    {
+        public const string StageConfig = "config";
+        public const string StagePhase = "phase";
+        public const string StageTrigger = "trigger";
+        public const string StageScope = "scope";
+        public const string StageExec = "exec";
+        public const string StageCollector = "collector";
+        public const string StageGuard = "guard";
+        public const string StageEmit = "emit";
+        public const string StageSuppress = "suppress";
+        public const string StageLogParser = "logparser";
+        public const string StageError = "error";
+
+        private const long DefaultMaxBytes = 10 * 1024 * 1024;
+
+        private readonly string _path;
+        private readonly long _maxBytes;
+        private readonly Action<string> _echo;
+        private readonly object _lock = new object();
+        private bool _headerWritten;
+
+        public GatherRuleDebugLog(string path, AgentLogger logger, Action<string> echo = null, long maxBytes = DefaultMaxBytes)
+        {
+            if (string.IsNullOrEmpty(path)) throw new ArgumentNullException(nameof(path));
+            _path = path;
+            _maxBytes = maxBytes;
+            _echo = echo;
+            logger?.Info($"GatherRuleDebugLog: enabled -> {path}");
+        }
+
+        /// <summary>
+        /// Writes one trace line: <c>{utc} | {ruleId} | {stage} | {message}</c>.
+        /// Newlines in <paramref name="message"/> are flattened except for the error
+        /// stage, where exception stack traces stay multi-line.
+        /// </summary>
+        public void Write(string ruleId, string stage, string message)
+        {
+            try
+            {
+                if (stage != StageError && message != null && message.IndexOf('\n') >= 0)
+                    message = message.Replace("\r", "").Replace('\n', ' ');
+
+                var line = $"{DateTime.UtcNow:yyyy-MM-ddTHH:mm:ss.fffZ} | {ruleId ?? "-"} | {stage} | {message}";
+
+                lock (_lock)
+                {
+                    EnsureFileReadyLocked();
+                    File.AppendAllText(_path, line + Environment.NewLine);
+                }
+
+                _echo?.Invoke(line);
+            }
+            catch { }
+        }
+
+        /// <summary>
+        /// One-shot helper for callers that have no executor (e.g. the flag is on but the
+        /// backend delivered zero gather rules) — the customer's trace file should explain
+        /// that too instead of silently not existing.
+        /// </summary>
+        public static void WriteStandalone(string path, string message, AgentLogger logger)
+        {
+            if (string.IsNullOrEmpty(path)) return;
+            try
+            {
+                new GatherRuleDebugLog(path, logger).Write(null, StageConfig, message);
+            }
+            catch { }
+        }
+
+        // Lazy on first write: create the directory and emit a header line. Before every
+        // append, rotate when the file exceeds maxBytes — keeping exactly one .old
+        // generation (worst case ~2x maxBytes on disk).
+        private void EnsureFileReadyLocked()
+        {
+            if (!_headerWritten)
+            {
+                var dir = Path.GetDirectoryName(_path);
+                if (!string.IsNullOrEmpty(dir))
+                    Directory.CreateDirectory(dir);
+            }
+
+            var info = new FileInfo(_path);
+            if (info.Exists && info.Length > _maxBytes)
+            {
+                var oldPath = Path.ChangeExtension(_path, null) + ".old.log";
+                if (File.Exists(oldPath))
+                    File.Delete(oldPath);
+                File.Move(_path, oldPath);
+                File.AppendAllText(_path,
+                    $"{DateTime.UtcNow:yyyy-MM-ddTHH:mm:ss.fffZ} | - | {StageConfig} | -- rotated (previous file exceeded {_maxBytes} bytes) --" + Environment.NewLine);
+            }
+
+            if (!_headerWritten)
+            {
+                File.AppendAllText(_path,
+                    $"{DateTime.UtcNow:yyyy-MM-ddTHH:mm:ss.fffZ} | - | {StageConfig} | -- gather rule debug log started --" + Environment.NewLine);
+                _headerWritten = true;
+            }
+        }
+    }
+}

src/Agent/AutopilotMonitor.Agent.V2.Core/Monitoring/Telemetry/Gather/GatherRuleExecutor.cs

@@ -22,6 +22,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather
     public class GatherRuleExecutor : IDisposable
     {
         private readonly AgentLogger _logger;
+        private readonly GatherRuleDebugLog _debug;   // null unless EnableGatherRuleDebugLog / --gather-debug-log
         private readonly GatherRuleContext _context;
         private readonly Dictionary<string, IGatherRuleCollector> _collectors;
 
@@ -61,7 +62,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather
         }
 
         public GatherRuleExecutor(string sessionId, string tenantId, Action<EnrollmentEvent> onEventCollected,
-            AgentLogger logger, string imeLogPathOverride = null)
+            AgentLogger logger, string imeLogPathOverride = null, string debugLogPath = null,
+            Action<string> debugEcho = null)
         {
             if (sessionId == null) throw new ArgumentNullException(nameof(sessionId));
             if (tenantId == null) throw new ArgumentNullException(nameof(tenantId));
@@ -69,9 +71,10 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather
             if (logger == null) throw new ArgumentNullException(nameof(logger));
 
             _logger = logger;
+            _debug = string.IsNullOrEmpty(debugLogPath) ? null : new GatherRuleDebugLog(debugLogPath, logger, debugEcho);
 
             var filePositionTracker = new LogFilePositionTracker();
-            _context = new GatherRuleContext(logger, sessionId, tenantId, onEventCollected, imeLogPathOverride, filePositionTracker);
+            _context = new GatherRuleContext(logger, sessionId, tenantId, onEventCollected, imeLogPathOverride, filePositionTracker, _debug);
 
             // Register all collector strategies
             var collectorList = new IGatherRuleCollector[]
@@ -96,6 +99,12 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather
             _collectors["command"] = _collectors["command_allowlisted"];
         }
 
+        /// <summary>
+        /// Null-safe write to the gather-rule debug trace. Never call while holding
+        /// <see cref="_scopeLock"/> — capture the message under the lock, write after release.
+        /// </summary>
+        private void DebugLog(string ruleId, string stage, string message) => _debug?.Write(ruleId, stage, message);
+
         /// <summary>
         /// Updates the active rules and starts/stops execution accordingly
         /// </summary>
@@ -111,11 +120,43 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather
 
             _activeRules = rules.Where(r => r.Enabled).ToList();
 
+            // Registration summary for the debug trace: one line per delivered rule so the
+            // customer can see exactly what the agent received and how it will be triggered.
+            if (_debug != null)
+            {
+                foreach (var rule in rules)
+                {
+                    if (!rule.Enabled)
+                    {
+                        DebugLog(rule.RuleId, GatherRuleDebugLog.StageConfig, "rule disabled — will never run");
+                        continue;
+                    }
+
+                    var scope = rule.ActivePhases != null && rule.ActivePhases.Count > 0
+                        ? $"activePhases=[{string.Join(",", rule.ActivePhases)}]"
+                        : !string.IsNullOrEmpty(rule.ActiveFromPhase)
+                            ? $"activeFromPhase={rule.ActiveFromPhase}"
+                            : "unscoped";
+                    DebugLog(rule.RuleId, GatherRuleDebugLog.StageConfig,
+                        $"registered: trigger={rule.Trigger}" +
+                        (string.IsNullOrEmpty(rule.TriggerPhase) ? "" : $" triggerPhase={rule.TriggerPhase}") +
+                        (string.IsNullOrEmpty(rule.TriggerEventType) ? "" : $" triggerEventType={rule.TriggerEventType}") +
+                        $", collector={rule.CollectorType}, target={rule.Target}, {scope}" +
+                        $", emitMode={(string.IsNullOrEmpty(rule.EmitMode) ? "always" : rule.EmitMode)}" +
+                        (rule.IntervalSeconds.HasValue ? $", interval={rule.IntervalSeconds}s" : ""));
+
+                    if (rule.Trigger == "interval" && !rule.IntervalSeconds.HasValue)
+                        DebugLog(rule.RuleId, GatherRuleDebugLog.StageError,
+                            "trigger=interval but intervalSeconds is missing — rule will NEVER run");
+                }
+            }
+
             // Execute startup rules — track completion via CountdownEvent so callers can wait.
             // Scoped startup rules that are not yet in scope are deferred: they run once from
             // OnPhaseChanged when their scope activates (same _startupRulesExecuted dedup — a
             // rule runs either here or there, never both). Unscoped rules behave as before.
             List<GatherRule> pendingStartup;
+            var deferredTraces = _debug != null ? new List<KeyValuePair<string, string>>() : null;
             lock (_scopeLock)
             {
                 // A config refresh may deliver new from-phase rules after their phase was
@@ -124,7 +165,15 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather
 
                 pendingStartup = _activeRules
                     .Where(r => r.Trigger == "startup" && !_startupRulesExecuted.Contains(r.RuleId))
-                    .Where(r => IsRuleInScopeLocked(r))
+                    .Where(r =>
+                    {
+                        string reason;
+                        var inScope = IsRuleInScopeLocked(r, out reason);
+                        if (!inScope && deferredTraces != null)
+                            deferredTraces.Add(new KeyValuePair<string, string>(r.RuleId,
+                                $"startup rule deferred — {reason}; runs once when its scope activates"));
+                        return inScope;
+                    })
                     .ToList();
 
                 foreach (var rule in pendingStartup)
@@ -133,6 +182,12 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather
                 }
             }
 
+            if (deferredTraces != null)
+            {
+                foreach (var trace in deferredTraces)
+                    DebugLog(trace.Key, GatherRuleDebugLog.StageScope, trace.Value);
+            }
+
             if (pendingStartup.Count > 0)
             {
                 _startupRulesLatch?.Dispose();
@@ -158,8 +213,12 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather
                 var timer = new Timer(
                     _ =>
                     {
-                        if (!IsRuleInScope(intervalRule))
+                        string skipReason;
+                        if (!IsRuleInScope(intervalRule, out skipReason))
+                        {
+                            DebugLog(intervalRule.RuleId, GatherRuleDebugLog.StageScope, $"interval tick skipped: {skipReason}");
                             return;
+                        }
                         ExecuteRule(intervalRule);
                     },
                     null,
@@ -168,6 +227,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather
                 );
                 _intervalTimers[intervalRule.RuleId] = timer;
                 _logger.Info($"  Interval rule {intervalRule.RuleId} scheduled every {intervalRule.IntervalSeconds}s");
+                DebugLog(intervalRule.RuleId, GatherRuleDebugLog.StageTrigger,
+                    $"interval timer scheduled every {intervalRule.IntervalSeconds}s (first run after one full interval — no immediate execution)");
             }
 
             _logger.Info($"GatherRuleExecutor: {_activeRules.Count(r => r.Trigger == "startup")} startup, " +
@@ -187,9 +248,11 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather
             // _currentPhase moves below. A transition INTO Failed still fires the exit rules of the
             // phase that failed — that snapshot is the whole point at a failure boundary.
             List<GatherRule> exitRules = null;
+            EnrollmentPhase previousPhase;
+            var exitTraces = _debug != null ? new List<KeyValuePair<string, string>>() : null;
             lock (_scopeLock)
             {
-                var previousPhase = _currentPhase;
+                previousPhase = _currentPhase;
                 if (previousPhase != EnrollmentPhase.Unknown && previousPhase != newPhase)
                 {
                     var previousPhaseName = previousPhase.ToString();
@@ -204,12 +267,22 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather
 
                         // Scope gate before the dedup add — an out-of-scope pass must not consume
                         // the once-per-(rule, phase) slot. IsRuleInScopeLocked still sees the old phase.
-                        if (!IsRuleInScopeLocked(rule)) continue;
+                        string scopeReason;
+                        if (!IsRuleInScopeLocked(rule, out scopeReason))
+                        {
+                            if (exitTraces != null)
+                                exitTraces.Add(new KeyValuePair<string, string>(rule.RuleId,
+                                    $"phase_exit of {previousPhaseName} skipped: {scopeReason}"));
+                            continue;
+                        }
 
                         // "exit:" prefix keeps this key space disjoint from the phase_change keys.
                         if (!_phaseRulesExecuted.Add($"exit:{rule.RuleId}|{previousPhaseName}"))
                         {
                             _logger.Debug($"Phase-exit rule {rule.RuleId} already executed for exit of {previousPhaseName}, skipping");
+                            if (exitTraces != null)
+                                exitTraces.Add(new KeyValuePair<string, string>(rule.RuleId,
+                                    $"phase_exit already executed for exit of {previousPhaseName} — once per (rule, phase)"));
                             continue;
                         }
 
@@ -219,6 +292,21 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather
                 }
             }
 
+            // Transition marker first, so every rule-level line below reads against it.
+            // Written outside _scopeLock like all trace lines.
+            if (previousPhase != newPhase)
+                DebugLog(null, GatherRuleDebugLog.StagePhase,
+                    $"phase change: {previousPhase} -> {phaseName}" +
+                    (previousPhase == EnrollmentPhase.Unknown
+                        ? " (first phase signal — scoped rules now evaluate against this phase)"
+                        : ""));
+
+            if (exitTraces != null)
+            {
+                foreach (var trace in exitTraces)
+                    DebugLog(trace.Key, GatherRuleDebugLog.StageScope, trace.Value);
+            }
+
             if (exitRules != null)
             {
                 foreach (var rule in exitRules)
@@ -252,6 +340,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather
             {
                 var deferredRule = rule;
                 _logger.Info($"Phase {phaseName} activated deferred startup rule {deferredRule.RuleId}");
+                DebugLog(deferredRule.RuleId, GatherRuleDebugLog.StageTrigger,
+                    $"phase {phaseName} activated deferred startup rule");
                 ThreadPool.QueueUserWorkItem(_ => ExecuteRule(deferredRule));
             }
 
@@ -262,18 +352,26 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather
                 {
                     // Scope gate BEFORE the dedup add — an out-of-scope pass must not consume
                     // the once-per-(rule, phase) execution slot.
-                    if (!IsRuleInScope(rule))
+                    string scopeReason;
+                    if (!IsRuleInScope(rule, out scopeReason))
+                    {
+                        DebugLog(rule.RuleId, GatherRuleDebugLog.StageScope,
+                            $"phase_change to {phaseName} skipped: {scopeReason}");
                         continue;
+                    }
 
                     // Deduplicate: only fire once per (ruleId, phase) combination
                     var deduplicationKey = $"{rule.RuleId}|{phaseName}";
                     if (!_phaseRulesExecuted.Add(deduplicationKey))
                     {
                         _logger.Debug($"Phase rule {rule.RuleId} already executed for phase {phaseName}, skipping");
+                        DebugLog(rule.RuleId, GatherRuleDebugLog.StageTrigger,
+                            $"phase_change already executed for phase {phaseName} — once per (rule, phase)");
                         continue;
                     }
 
                     _logger.Info($"Phase change triggered rule {rule.RuleId} (phase: {phaseName})");
+                    DebugLog(rule.RuleId, GatherRuleDebugLog.StageTrigger, $"phase_change to {phaseName} fired");
                     ThreadPool.QueueUserWorkItem(_ => ExecuteRule(rule));
                 }
             }
@@ -288,10 +386,16 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather
             {
                 if (string.Equals(rule.TriggerEventType, eventType, StringComparison.OrdinalIgnoreCase))
                 {
-                    if (!IsRuleInScope(rule))
+                    string scopeReason;
+                    if (!IsRuleInScope(rule, out scopeReason))
+                    {
+                        DebugLog(rule.RuleId, GatherRuleDebugLog.StageScope,
+                            $"on_event {eventType} skipped: {scopeReason}");
                         continue;
+                    }
 
                     _logger.Info($"Event triggered rule {rule.RuleId} (event: {eventType})");
+                    DebugLog(rule.RuleId, GatherRuleDebugLog.StageTrigger, $"on_event {eventType} fired");
                     ThreadPool.QueueUserWorkItem(_ => ExecuteRule(rule));
                 }
             }
@@ -302,6 +406,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather
             try
             {
                 _logger.Info($"Executing gather rule: {rule.RuleId} ({rule.Title})");
+                DebugLog(rule.RuleId, GatherRuleDebugLog.StageExec, $"executing: collector={rule.CollectorType}, target={rule.Target}");
 
                 var collectorType = rule.CollectorType?.ToLower();
 
@@ -309,6 +414,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather
                 if (collectorType == null || !_collectors.TryGetValue(collectorType, out collector))
                 {
                     _logger.Warning($"Unknown collector type: {rule.CollectorType} for rule {rule.RuleId}");
+                    DebugLog(rule.RuleId, GatherRuleDebugLog.StageError, $"unknown collector type '{rule.CollectorType}' — nothing emitted");
                     return;
                 }
 
@@ -316,7 +422,19 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather
 
                 // LogParser (and potentially others) emit events directly and return null
                 if (result == null)
+                {
+                    DebugLog(rule.RuleId, GatherRuleDebugLog.StageCollector,
+                        collectorType == "logparser"
+                            ? "logparser emits per-match events directly — see logparser lines above for the per-file outcome"
+                            : "collector returned null — nothing emitted");
                     return;
+                }
+
+                if (result.Count == 0)
+                {
+                    DebugLog(rule.RuleId, GatherRuleDebugLog.StageCollector,
+                        "collector returned EMPTY result — nothing emitted (typical causes: target not found with emitOnlyIfExists, or guard block — see guard line if present)");
+                }
 
                 if (result.Count > 0)
                 {
@@ -325,8 +443,19 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather
                     // empty result never reaches this point, so an emitOnlyIfExists miss neither
                     // emits nor updates the hash — composing to "one event on appearance, then
                     // only on change".
-                    if (IsOnChangeMode(rule) && !ShouldEmitOnChange(rule, result))
-                        return;
+                    if (IsOnChangeMode(rule))
+                    {
+                        string hashPrefix;
+                        int suppressedStreak;
+                        if (!ShouldEmitOnChange(rule, result, out hashPrefix, out suppressedStreak))
+                        {
+                            DebugLog(rule.RuleId, GatherRuleDebugLog.StageSuppress,
+                                $"result unchanged (hash {hashPrefix}) — emit suppressed (on_change), suppressed streak={suppressedStreak}");
+                            return;
+                        }
+                        DebugLog(rule.RuleId, GatherRuleDebugLog.StageEmit,
+                            $"result changed (hash {hashPrefix})" + (suppressedStreak > 0 ? $" after {suppressedStreak} suppressed polls" : ""));
+                    }
 
                     result["ruleId"] = rule.RuleId;
                     result["ruleTitle"] = rule.Title;
@@ -357,11 +486,15 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather
                         Message = $"Gather: {rule.Title}",
                         Data = result
                     });
+                    DebugLog(rule.RuleId, GatherRuleDebugLog.StageEmit,
+                        $"emitted {eventType} (severity={severity}, {result.Count} fields)");
                 }
             }
             catch (Exception ex)
             {
                 _logger.Warning($"Gather rule {rule.RuleId} failed: {ex.Message}");
+                // Full exception incl. stack trace only in the debug trace — the agent log stays terse.
+                DebugLog(rule.RuleId, GatherRuleDebugLog.StageError, $"rule execution failed: {ex}");
             }
         }
 
@@ -375,15 +508,33 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather
 
         // Internal so the scope matrix is testable synchronously (no timer/ThreadPool races).
         internal bool IsRuleInScope(GatherRule rule)
+        {
+            string reason;
+            return IsRuleInScope(rule, out reason);
+        }
+
+        /// <summary>
+        /// Scope gate with a human-readable skip reason for the debug trace. The reason is
+        /// captured under the lock but must be WRITTEN outside it (never trace under _scopeLock).
+        /// </summary>
+        internal bool IsRuleInScope(GatherRule rule, out string reason)
         {
             lock (_scopeLock)
             {
-                return IsRuleInScopeLocked(rule);
+                return IsRuleInScopeLocked(rule, out reason);
             }
         }
 
         private bool IsRuleInScopeLocked(GatherRule rule)
         {
+            string reason;
+            return IsRuleInScopeLocked(rule, out reason);
+        }
+
+        private bool IsRuleInScopeLocked(GatherRule rule, out string reason)
+        {
+            reason = null;
+
             if (!HasPhaseScope(rule))
                 return true; // unscoped — legacy behavior
 
@@ -400,7 +551,10 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather
                 // No phase signal yet (or scope tokens that never match, e.g. "Unknown"):
                 // scoped rules stay inactive.
                 if (_currentPhase == EnrollmentPhase.Unknown)
+                {
+                    reason = "currentPhase=Unknown — scoped rules stay inactive until the first phase signal";
                     return false;
+                }
 
                 var phaseName = _currentPhase.ToString();
                 foreach (var phase in rule.ActivePhases)
@@ -408,10 +562,15 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather
                     if (string.Equals(phase, phaseName, StringComparison.OrdinalIgnoreCase))
                         return true;
                 }
+                reason = $"out of scope (currentPhase={phaseName}, activePhases=[{string.Join(",", rule.ActivePhases)}])";
                 return false;
             }
 
-            return _fromPhaseLatched.Contains(rule.RuleId);
+            if (_fromPhaseLatched.Contains(rule.RuleId))
+                return true;
+
+            reason = $"activeFromPhase={rule.ActiveFromPhase} not latched yet (currentPhase={_currentPhase})";
+            return false;
         }
 
         /// <summary>
@@ -457,8 +616,23 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather
         /// Internal so the state machine is testable synchronously (no timer/ThreadPool races).
         /// </summary>
         internal bool ShouldEmitOnChange(GatherRule rule, Dictionary<string, object> result)
+        {
+            string hashPrefix;
+            int suppressedStreak;
+            return ShouldEmitOnChange(rule, result, out hashPrefix, out suppressedStreak);
+        }
+
+        /// <summary>
+        /// Overload exposing the hash prefix and suppression streak for the debug trace:
+        /// on suppress, <paramref name="suppressedStreak"/> is the updated streak count;
+        /// on emit, it is the streak that just ended (0 when none).
+        /// </summary>
+        internal bool ShouldEmitOnChange(GatherRule rule, Dictionary<string, object> result,
+            out string hashPrefix, out int suppressedStreak)
         {
             var hash = ComputeCanonicalHash(result);
+            hashPrefix = hash.Length > 8 ? hash.Substring(0, 8) : hash;
+            suppressedStreak = 0;
             bool emit;
             lock (_scopeLock)
             {
@@ -469,6 +643,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather
                     _suppressed[rule.RuleId] = _suppressed.TryGetValue(rule.RuleId, out streak)
                         ? (streak.Count + 1, streak.SinceUtc)
                         : (1, DateTime.UtcNow);
+                    suppressedStreak = _suppressed[rule.RuleId].Count;
                     emit = false;
                 }
                 else
@@ -479,6 +654,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Gather
                     {
                         result["suppressedPolls"] = streak.Count;
                         result["suppressedSinceUtc"] = streak.SinceUtc.ToString("o", CultureInfo.InvariantCulture);
+                        suppressedStreak = streak.Count;
                     }
                     _suppressed.Remove(rule.RuleId);
                     emit = true;

src/Agent/AutopilotMonitor.Agent.V2.Core/Monitoring/Telemetry/Periodic/NetworkChangeDetector.cs

@@ -8,8 +8,8 @@ using System.Net.Sockets;
 using System.Threading;
 using System.Threading.Tasks;
 using AutopilotMonitor.Agent.V2.Core.Logging;
+using AutopilotMonitor.Agent.V2.Core.Monitoring.Interop;
 using AutopilotMonitor.Agent.V2.Core.Orchestration;
-using AutopilotMonitor.Agent.V2.Core.Security;
 using AutopilotMonitor.Shared;
 using AutopilotMonitor.Shared.Models;
 
@@ -37,7 +37,6 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Periodic
         private const int DebounceDelayMs = 3000;
         private const int ConnectivityCheckDelayMs = 5000;
         private const int ConnectivityCheckTimeoutMs = 8000;
-        private const int WifiCollectTimeoutMs = 3000;
         private const string Source = "NetworkChangeDetector";
 
         /// <summary>
@@ -374,7 +373,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Periodic
                 // Collect WiFi SSID synchronously (needed for before/after comparison)
                 if (isWifi)
                 {
-                    var wifiInfo = CollectWiFiInfo();
+                    Guid? nicGuid = Guid.TryParse(activeNic.Id, out var parsedGuid) ? parsedGuid : (Guid?)null;
+                    var wifiInfo = CollectWiFiInfo(nicGuid);
                     snapshot.WifiSsid = wifiInfo.ssid;
                     snapshot.WifiSignalPercent = wifiInfo.signal;
                     snapshot.WifiRadioType = wifiInfo.radioType;
@@ -390,73 +390,30 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Telemetry.Periodic
         }
 
         /// <summary>
-        /// Collects WiFi SSID, signal, and radio type via netsh wlan show interfaces.
-        /// Synchronous with timeout — needed before emitting the event.
+        /// Collects WiFi SSID, signal, and radio type via the native WLAN API
+        /// (<see cref="WifiInfoReader"/> — language-neutral, no process spawn).
+        /// Synchronous — needed before emitting the event.
         /// </summary>
-        private (string ssid, int? signal, string radioType) CollectWiFiInfo()
+        private (string ssid, int? signal, string radioType) CollectWiFiInfo(Guid? interfaceGuid)
         {
-            string ssid = null;
-            int? signal = null;
-            string radioType = null;
-
             try
             {
-                var psi = new ProcessStartInfo
+                var wifi = WifiInfoReader.TryGetCurrentConnection(interfaceGuid, out var wifiDiag);
+                if (wifi == null)
                 {
-                    FileName = SystemPaths.Netsh,
-                    Arguments = "wlan show interfaces",
-                    UseShellExecute = false,
-                    RedirectStandardOutput = true,
-                    RedirectStandardError = true,
-                    CreateNoWindow = true
-                };
-
-                string output;
-                using (var process = Process.Start(psi))
-                {
-                    output = process.StandardOutput.ReadToEnd();
-                    if (!process.WaitForExit(WifiCollectTimeoutMs))
-                    {
-                        try { process.Kill(); } catch { }
-                        _logger.Debug("NetworkChangeDetector: netsh timed out");
-                        return (null, null, null);
-                    }
+                    _logger.Debug($"NetworkChangeDetector: native WLAN API returned no WiFi info ({wifiDiag ?? "no connected WLAN interface"}) — trying netsh fallback");
+                    wifi = NetshWifiFallback.TryRead();
                 }
 
-                if (string.IsNullOrEmpty(output))
-                    return (null, null, null);
-
-                foreach (var line in output.Split(new[] { '\r', '\n' }, StringSplitOptions.RemoveEmptyEntries))
-                {
-                    var trimmed = line.Trim();
-                    var colonIndex = trimmed.IndexOf(':');
-                    if (colonIndex < 0) continue;
-
-                    var key = trimmed.Substring(0, colonIndex).Trim();
-                    var value = trimmed.Substring(colonIndex + 1).Trim();
-
-                    if (key.Equals("SSID", StringComparison.OrdinalIgnoreCase) &&
-                        !key.Equals("BSSID", StringComparison.OrdinalIgnoreCase))
-                    {
-                        ssid = value;
-                    }
-                    else if (key.Equals("Signal", StringComparison.OrdinalIgnoreCase))
-                    {
-                        if (int.TryParse(value.TrimEnd('%'), out var sig))
-                            signal = sig;
-                    }
-                    else if (key.Equals("Radio type", StringComparison.OrdinalIgnoreCase))
-                    {
-                        radioType = value;
-                    }
-                }
+                if (wifi != null)
+                    return (wifi.Ssid, wifi.SignalPercent, wifi.RadioType);
             }
             catch (Exception ex)
             {
                 _logger.Debug($"NetworkChangeDetector: WiFi info collection failed: {ex.Message}");
             }
 
-            return (ssid, signal, radioType);
+            return (null, null, null);
         }
 
         // -------------------------------------------------------------------

src/Agent/AutopilotMonitor.Agent.V2.Core/Monitoring/Transport/DistressReporter.cs

@@ -56,6 +56,10 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Transport
         private DateTime? _lastReportTime;
         private int _reportCount;
 
+        // Local W365 marker verdict, captured once at construction (same UNVERIFIED contract
+        // as the hardware fields). Optional ctor arg so test fakes stay source-compatible.
+        private readonly bool _isCloudPc;
+
         public DistressReporter(
             string baseUrl,
             string tenantId,
@@ -64,7 +68,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Transport
             string serialNumber,
             string agentVersion,
             AgentLogger logger,
-            X509Certificate2 clientCertificate = null)
+            X509Certificate2 clientCertificate = null,
+            bool isCloudPc = false)
         {
             _tenantId = tenantId;
             _manufacturer = manufacturer;
@@ -72,6 +77,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Transport
             _serialNumber = serialNumber;
             _agentVersion = agentVersion;
             _logger = logger;
+            _isCloudPc = isCloudPc;
 
             // Capture cert context. Each field is independently nullable so the backend can tell
             // "agent had no cert at all" (NoCertInStore + all-null fields) from "agent had a cert
@@ -169,6 +175,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Monitoring.Transport
                 HttpStatusCode = httpStatusCode,
                 Message = Truncate(message, 256),
                 Timestamp = DateTime.UtcNow,
+                IsCloudPc = _isCloudPc,
                 CertSourceState = _capturedCertState,
                 CertThumbprint = _capturedCertThumbprint,
                 CertSubject = Truncate(_capturedCertSubject, 96),

src/Agent/AutopilotMonitor.Agent.V2.Core/Orchestration/DefaultComponentFactory.cs

@@ -97,7 +97,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
             IReadOnlyCollection<string> whiteGloveSealingPatternIds,
             ISignalIngressSink ingress,
             IClock clock,
-            Transport.Telemetry.ITelemetrySpool? telemetrySpool)
+            Transport.Telemetry.ITelemetrySpool? telemetrySpool,
+            TimelineEventStream? timelineEvents = null)
         {
             if (string.IsNullOrEmpty(sessionId)) throw new ArgumentException("SessionId required.", nameof(sessionId));
             if (string.IsNullOrEmpty(tenantId)) throw new ArgumentException("TenantId required.", nameof(tenantId));
@@ -471,8 +472,10 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
             if (officeHost != null) hosts.Add(officeHost);
 
             // M4.6.δ — Gather-rules runtime executor. Runs "startup" rules once the agent is up
-            // and "interval" rules on their timers; "phase_change" / "on_event" rules are driven
-            // by the host's SignalIngress.SignalPosted subscription (MON-A1).
+            // and "interval" rules on their timers; "phase_change" / "phase_exit" / "on_event"
+            // rules are driven by the post-reduce TimelineEventStream (emitted timeline events),
+            // NOT the raw SignalPosted stream — the raw phase can run minutes ahead of the
+            // engine-declared one (RealmJoin gate, session 32312a32). See TimelineEventStream doc.
             if (_remoteConfig.GatherRules != null && _remoteConfig.GatherRules.Count > 0)
             {
                 hosts.Add(new GatherRuleExecutorHost(
@@ -483,7 +486,17 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
                     logger: logger,
                     rules: _remoteConfig.GatherRules,
                     imeLogPathOverride: _agentConfig.ImeLogPathOverride,
-                    unrestrictedMode: _agentConfig.UnrestrictedMode));
+                    unrestrictedMode: _agentConfig.UnrestrictedMode,
+                    gatherDebugLogPath: _agentConfig.GatherRuleDebugLogPath,
+                    timelineEvents: timelineEvents));
+            }
+            else if (!string.IsNullOrEmpty(_agentConfig.GatherRuleDebugLogPath))
+            {
+                // Debug trace is on but the backend delivered zero gather rules — the trace
+                // file must say so instead of silently not existing.
+                Monitoring.Telemetry.Gather.GatherRuleDebugLog.WriteStandalone(
+                    _agentConfig.GatherRuleDebugLogPath,
+                    "no gather rules delivered by backend — nothing to execute", logger);
             }
 
             return new CollectorSurfaces(hosts, imeLogHost, espAndHelloHost, aadJoinHost);

src/Agent/AutopilotMonitor.Agent.V2.Core/Orchestration/EnrollmentOrchestrator.cs

@@ -107,6 +107,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
         private TelemetrySignalEmitter? _signalEmitter;
         private TelemetryTransitionEmitter? _transitionEmitter;
         private EventTimelineEmitter? _timelineEmitter;
+        private TimelineEventStream? _timelineEvents;
         private BackPressureEventObserver? _backPressureObserver;
         private IDeadlineScheduler? _scheduler;
         private ClassifierRegistry? _classifierRegistry;
@@ -413,7 +414,12 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
                 _transport, _eventSequenceCounter, _sessionId, _tenantId, _traceEventsEnabled);
             _signalEmitter = new TelemetrySignalEmitter(_transport, _sessionId, _tenantId);
             _transitionEmitter = new TelemetryTransitionEmitter(_transport, _sessionId, _tenantId);
-            _timelineEmitter = new EventTimelineEmitter(eventEmitter);
+            // Post-reduce timeline observer: EventTimelineEmitter publishes every emitted event's
+            // (eventType, phase) here. Fed to the collector-host factory at step 14 so gather-rule
+            // phase_change/on_event triggers key off the ENGINE-REDUCED timeline (RealmJoin gate
+            // et al. respected) instead of raw pre-reduce signals — see TimelineEventStream doc.
+            _timelineEvents = new TimelineEventStream();
+            _timelineEmitter = new EventTimelineEmitter(eventEmitter, _timelineEvents);
             _backPressureObserver = new BackPressureEventObserver(eventEmitter, _clock);
 
             // 5) Deadlines + Classifiers.
@@ -653,7 +659,8 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
             {
                 var surfaces = _componentFactory.CreateCollectorHosts(
                     _sessionId, _tenantId, _logger, _whiteGloveSealingPatternIds,
-                    ingress: _ingress, clock: _clock, telemetrySpool: _spool);
+                    ingress: _ingress, clock: _clock, telemetrySpool: _spool,
+                    timelineEvents: _timelineEvents);
                 CollectorSurfaces = surfaces;
                 _collectorHosts = surfaces.Hosts;
                 foreach (var host in _collectorHosts)

src/Agent/AutopilotMonitor.Agent.V2.Core/Orchestration/Hosts/DeliveryOptimizationHost.cs

@@ -51,7 +51,9 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
                 getPackageStates: () => imeHost.PackageStates,
                 onDoTelemetryReceived: pkg =>
                 {
-                    try { imeHost.Tracker.OnDoTelemetryReceived?.Invoke(pkg); }
+                    // null source timestamp: poll-driven completion, no log line backs it —
+                    // the adapter stamps the clock instead of LastMatchedLogTimestamp.
+                    try { imeHost.Tracker.OnDoTelemetryReceived?.Invoke(pkg, null); }
                     catch (Exception ex) { logger.Warning($"DeliveryOptimizationHost: OnDoTelemetryReceived invocation threw: {ex.Message}"); }
                 },
                 logDirectory: Environment.ExpandEnvironmentVariables(Constants.LogDirectory),

src/Agent/AutopilotMonitor.Agent.V2.Core/Orchestration/Hosts/GatherRuleExecutorHost.cs

@@ -4,7 +4,6 @@ using System.Collections.Generic;
 using System.Threading;
 using AutopilotMonitor.Agent.V2.Core.Logging;
 using AutopilotMonitor.DecisionCore.Engine;
-using AutopilotMonitor.DecisionCore.Signals;
 using AutopilotMonitor.Shared.Models;
 
 namespace AutopilotMonitor.Agent.V2.Core.Orchestration
@@ -19,17 +18,24 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
         private readonly bool _unrestrictedMode;
         private int _disposed;
 
-        // MON-A1: drive phase_change / on_event gather triggers from the central signal stream.
-        // V1 fired these from MonitoringService on every EnrollmentEvent (OnPhaseChanged(evt.Phase)
-        // on phase change + OnEvent(evt.EventType) per event); the V2 host previously only called
-        // UpdateRules, so 5 of 10 shipped rules (incl. the only enabled one, dsregcmd at
-        // FinalizingSetup) silently never fired. In V2 every event is an InformationalEvent signal
-        // carrying eventType + (optional) phase in its payload. Null on test fakes / non-SignalIngress
-        // sinks — then signal-triggers degrade off (startup + interval rules still run).
-        private readonly SignalIngress? _observableIngress;
-        private Action<DecisionSignalKind, IReadOnlyDictionary<string, string>?>? _signalPostedHandler;
+        // MON-A1 (revised): drive phase_change / phase_exit / on_event gather triggers from the
+        // POST-REDUCE emitted timeline (TimelineEventStream), not from the raw signal stream.
+        // V1 fired these from MonitoringService on every emitted EnrollmentEvent; the first V2
+        // wiring subscribed to SignalIngress.SignalPosted instead, which fires at enqueue time
+        // with the RAW collector payload — before the reducer has applied gates like the
+        // RealmJoin completion gate. Consequence (session 32312a32, rsneuffen.de): a phase_change
+        // rule on FinalizingSetup fired at the raw EspPhaseChanged(FinalizingSetup) signal (ESP
+        // exit / Hello wizard), 7 minutes before the engine declared phase_transition(FinalizingSetup)
+        // on the timeline — and before the RealmJoin package wrote the registry key the rule was
+        // built to read. The raw feed also never carried engine-emitted event types at all, so
+        // on_event rules on enrollment_complete (documented) could never fire. The emitted-event
+        // feed restores V1 semantics and matches what the UI timeline shows ("collect once when
+        // the enrollment reaches this phase"). Null on test fakes / standalone configurations —
+        // then phase/event triggers degrade off (startup + interval rules still run).
+        private readonly TimelineEventStream? _timelineEvents;
+        private Action<string, EnrollmentPhase>? _timelineHandler;
         private readonly object _sync = new object();
-        private string? _lastPhaseName;
+        private EnrollmentPhase _lastPhase = EnrollmentPhase.Unknown;
 
         public GatherRuleExecutorHost(
             string sessionId,
@@ -39,7 +45,9 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
             AgentLogger logger,
             List<GatherRule> rules,
             string? imeLogPathOverride,
-            bool unrestrictedMode = false)
+            bool unrestrictedMode = false,
+            string? gatherDebugLogPath = null,
+            TimelineEventStream? timelineEvents = null)
         {
             if (ingress == null) throw new ArgumentNullException(nameof(ingress));
             if (clock == null) throw new ArgumentNullException(nameof(clock));
@@ -55,10 +63,11 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
             // session mode we wrap post.Emit so every session-mode gather event still
             // flows through the InformationalEvent ingress pipe before hitting the
             // telemetry spool — Rail-A semantics for ordering / replay determinism.
-            var post = new InformationalEventPost(ingress, clock);
+            var post = new InformationalEventPost(ingress, clock, logger);
             _executor = new Monitoring.Telemetry.Gather.GatherRuleExecutor(
-                sessionId, tenantId, evt => post.Emit(evt), logger, imeLogPathOverride);
-            _observableIngress = ingress as SignalIngress;
+                sessionId, tenantId, evt => post.Emit(evt), logger, imeLogPathOverride,
+                debugLogPath: gatherDebugLogPath);
+            _timelineEvents = timelineEvents;
         }
 
         public void Start()
@@ -69,46 +78,43 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
             _executor.UnrestrictedMode = _unrestrictedMode;
             _executor.UpdateRules(_rules);
 
-            // MON-A1: observe the central signal stream so phase_change / on_event rules fire.
-            if (_observableIngress != null && _signalPostedHandler == null)
+            // MON-A1 (revised): observe the emitted timeline so phase/event triggers fire in
+            // step with what the timeline actually shows.
+            if (_timelineEvents != null && _timelineHandler == null)
             {
-                _signalPostedHandler = OnSignalPosted;
-                _observableIngress.SignalPosted += _signalPostedHandler;
+                _timelineHandler = OnTimelineEventEmitted;
+                _timelineEvents.EventEmitted += _timelineHandler;
             }
 
             _logger.Info(
-                $"GatherRuleExecutorHost: started with {_rules.Count} rule(s), unrestrictedMode={_unrestrictedMode}, signalTriggers={(_observableIngress != null)}.");
+                $"GatherRuleExecutorHost: started with {_rules.Count} rule(s), unrestrictedMode={_unrestrictedMode}, timelineTriggers={(_timelineEvents != null)}.");
         }
 
         /// <summary>
-        /// Translates posted signals into the executor's phase_change / on_event triggers (MON-A1).
-        /// Phase: fire <see cref="Monitoring.Telemetry.Gather.GatherRuleExecutor.OnPhaseChanged"/> when
-        /// the observed phase changes and parses to an <see cref="EnrollmentPhase"/> (raw collector
-        /// phase strings that aren't enum names are ignored — they carry no gather-rule meaning).
-        /// Event: fire <see cref="Monitoring.Telemetry.Gather.GatherRuleExecutor.OnEvent"/> for every
-        /// InformationalEvent's eventType. The executor dispatches rule execution on the ThreadPool,
-        /// so this stays off the signal-posting hot path; it also dedups phase rules per (rule, phase).
+        /// Translates emitted timeline events into the executor's triggers. Phase: fire
+        /// <see cref="Monitoring.Telemetry.Gather.GatherRuleExecutor.OnPhaseChanged"/> when a
+        /// phase-declaration event (Phase != Unknown) moves the timeline to a new phase — this
+        /// is by construction the engine-reduced phase, so deferred transitions (RealmJoin gate)
+        /// fire the rules exactly when the timeline shows them. Event: fire
+        /// <see cref="Monitoring.Telemetry.Gather.GatherRuleExecutor.OnEvent"/> for every emitted
+        /// event's type — including engine-emitted types (enrollment_complete, phase_transition,
+        /// realmjoin_resolved, …) that never existed on the raw signal stream. The executor
+        /// dispatches rule execution on the ThreadPool, so this stays off the ingress worker's
+        /// effect path; it also dedups phase rules per (rule, phase).
         /// </summary>
-        private void OnSignalPosted(DecisionSignalKind kind, IReadOnlyDictionary<string, string>? payload)
+        private void OnTimelineEventEmitted(string eventType, EnrollmentPhase phase)
         {
-            if (payload == null) return;
-
             try
             {
                 lock (_sync)
                 {
-                    if (payload.TryGetValue(SignalPayloadKeys.EspPhase, out var phaseName)
-                        && !string.IsNullOrEmpty(phaseName)
-                        && !string.Equals(phaseName, _lastPhaseName, StringComparison.OrdinalIgnoreCase)
-                        && Enum.TryParse<EnrollmentPhase>(phaseName, ignoreCase: true, out var phase))
+                    if (phase != EnrollmentPhase.Unknown && phase != _lastPhase)
                     {
-                        _lastPhaseName = phaseName;
+                        _lastPhase = phase;
                         _executor.OnPhaseChanged(phase);
                     }
 
-                    if (kind == DecisionSignalKind.InformationalEvent
-                        && payload.TryGetValue(SignalPayloadKeys.EventType, out var eventType)
-                        && !string.IsNullOrEmpty(eventType))
+                    if (!string.IsNullOrEmpty(eventType))
                     {
                         _executor.OnEvent(eventType);
                     }
@@ -116,17 +122,17 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
             }
             catch (Exception ex)
             {
-                _logger.Verbose($"GatherRuleExecutorHost: signal-trigger dispatch failed: {ex.Message}");
+                _logger.Verbose($"GatherRuleExecutorHost: timeline-trigger dispatch failed: {ex.Message}");
             }
         }
 
         public void Stop()
         {
-            if (_observableIngress != null && _signalPostedHandler != null)
+            if (_timelineEvents != null && _timelineHandler != null)
             {
-                try { _observableIngress.SignalPosted -= _signalPostedHandler; }
+                try { _timelineEvents.EventEmitted -= _timelineHandler; }
                 catch { /* best-effort unsubscribe during shutdown */ }
-                _signalPostedHandler = null;
+                _timelineHandler = null;
             }
             // GatherRuleExecutor is IDisposable; no explicit Stop beyond unsubscribe. Rely on Dispose.
         }

src/Agent/AutopilotMonitor.Agent.V2.Core/Orchestration/IComponentFactory.cs

@@ -39,6 +39,13 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
         /// <c>spool.pendingItemCount</c> / <c>spool.fileSizeBytes</c>. Nullable — fakes and
         /// spool-less configurations pass null and the metrics fields are simply absent.
         /// </para>
+        /// <para>
+        /// <paramref name="timelineEvents"/> flows into the <c>GatherRuleExecutorHost</c> so
+        /// <c>phase_change</c> / <c>phase_exit</c> / <c>on_event</c> gather triggers key off the
+        /// ENGINE-REDUCED emitted timeline (post-reduce, RealmJoin gate respected) instead of raw
+        /// pre-reduce signals — see <see cref="TimelineEventStream"/>. Nullable — fakes pass null
+        /// and the host's phase/event triggers degrade off (startup + interval rules still run).
+        /// </para>
         /// </summary>
         CollectorSurfaces CreateCollectorHosts(
             string sessionId,
@@ -47,6 +54,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Orchestration
             IReadOnlyCollection<string> whiteGloveSealingPatternIds,
             ISignalIngressSink ingress,
             IClock clock,
-            Transport.Telemetry.ITelemetrySpool? telemetrySpool);
+            Transport.Telemetry.ITelemetrySpool? telemetrySpool,
+            TimelineEventStream? timelineEvents = null);
     }
 }

src/Agent/AutopilotMonitor.Agent.V2.Core/Orchestration/TimelineEventStream.cs

@@ -0,0 +1,55 @@
+#nullable enable
+using System;
+using AutopilotMonitor.Shared.Models;
+
+namespace AutopilotMonitor.Agent.V2.Core.Orchestration
+{
+    /// <summary>
+    /// Post-reduce observer surface for emitted timeline events: <see cref="Telemetry.Events.EventTimelineEmitter"/>
+    /// publishes every <see cref="EnrollmentEvent"/> it emits as an <c>(eventType, phase)</c> pair,
+    /// AFTER the decision engine has reduced the originating signal and its effects have been
+    /// executed.
+    /// <para>
+    /// This is deliberately different from <see cref="SignalIngress.SignalPosted"/>, which fires
+    /// at enqueue time on the producer thread and therefore only ever carries the RAW collector
+    /// payload — before the reducer has applied gates like the RealmJoin completion gate that can
+    /// defer or suppress a phase transition. Consumers that must agree with what the timeline
+    /// actually shows (the gather-rule phase/event triggers) subscribe here, not to the raw
+    /// signal stream. See session 32312a32: a <c>phase_change</c> gather rule on FinalizingSetup
+    /// fired at the raw <c>EspPhaseChanged(FinalizingSetup)</c> signal (ESP exit), 7 minutes
+    /// before the engine — deferred behind the RealmJoin gate — actually declared
+    /// <c>phase_transition(FinalizingSetup)</c> on the timeline.
+    /// </para>
+    /// <para>
+    /// <b>Threading</b>: <see cref="Publish"/> runs on the ingress worker thread (the effect
+    /// execution path). Subscribers must stay fast and must not block; subscriber exceptions are
+    /// swallowed per handler so the emit path can never throw (an exception here would surface
+    /// as an EffectRunner transient retry and duplicate the emitted event).
+    /// </para>
+    /// </summary>
+    public sealed class TimelineEventStream
+    {
+        /// <summary>
+        /// Raised once per emitted timeline event with its <see cref="EnrollmentEvent.EventType"/>
+        /// and parsed <see cref="EnrollmentEvent.Phase"/> (<see cref="EnrollmentPhase.Unknown"/>
+        /// for the vast majority of events — only phase-declaration events carry a real phase,
+        /// which is exactly the set the UI timeline groups on).
+        /// </summary>
+        public event Action<string, EnrollmentPhase>? EventEmitted;
+
+        internal void Publish(string eventType, EnrollmentPhase phase)
+        {
+            var handler = EventEmitted;
+            if (handler == null) return;
+
+            foreach (Action<string, EnrollmentPhase> subscriber in handler.GetInvocationList())
+            {
+                try { subscriber(eventType, phase); }
+                catch
+                {
+                    // Subscriber isolation — see class doc: the emit path must never throw.
+                }
+            }
+        }
+    }
+}

src/Agent/AutopilotMonitor.Agent.V2.Core/Security/CloudPcDetector.cs

@@ -0,0 +1,77 @@
+using System;
+using Microsoft.Win32;
+
+namespace AutopilotMonitor.Agent.V2.Core.Security
+{
+    /// <summary>
+    /// Detects whether the agent runs on a Windows 365 Cloud PC, using the same marker
+    /// evidence the bootstrap script's <c>Test-IsCloudPc</c> settled on after the first
+    /// W365 field test (2026-08-06) disproved WMI-model matching (a Cloud PC reports only
+    /// Manufacturer='Microsoft Corporation' + Model='Virtual Machine' locally — identical
+    /// to any Hyper-V VM):
+    /// <list type="bullet">
+    ///   <item><c>HKLM\SOFTWARE\Microsoft\Windows365</c> exists, AND</item>
+    ///   <item>the <c>CloudManagedDesktopExtension</c> service (Microsoft Cloud Managed
+    ///         Desktop Extension, the W365 management agent that runs ON Cloud PCs) is
+    ///         installed — probed via its <c>HKLM\SYSTEM\CurrentControlSet\Services</c> key,
+    ///         so the agent needs no System.ServiceProcess dependency.</item>
+    /// </list>
+    /// BOTH markers are required (AND): each alone has plausible look-alikes (W365-Boot
+    /// physical clients may carry Windows365 policy state; the MCMD agent family also
+    /// served other managed-desktop offerings).
+    /// <para>
+    /// Display/context metadata only — the flag rides on <c>SessionRegistration</c> and the
+    /// <c>EnrollmentFactsObserved</c> signal. It is NEVER an auth input: backend device
+    /// validation trusts exclusively the cert-CN-bound Graph lookup
+    /// (<c>CloudPcDeviceValidator</c>), not this locally-derived value.
+    /// Exception-swallowing, false on any error — mirrors the SKIP-safe bootstrap contract
+    /// and the <see cref="EnrollmentRegistryDetector"/> degradation rules.
+    /// </para>
+    /// </summary>
+    public static class CloudPcDetector
+    {
+        internal const string Windows365MarkerKey = @"SOFTWARE\Microsoft\Windows365";
+        internal const string CmdeServiceKey = @"SYSTEM\CurrentControlSet\Services\CloudManagedDesktopExtension";
+
+        public static bool DetectIsCloudPc()
+        {
+            try
+            {
+                return ResolveIsCloudPc(SubKeyExists);
+            }
+            catch
+            {
+                return false;
+            }
+        }
+
+        /// <summary>
+        /// Pure decision logic for <see cref="DetectIsCloudPc"/>. Exposed internally so the
+        /// marker-AND semantics can be exercised without a real registry (same seam contract
+        /// as <see cref="EnrollmentRegistryDetector.ResolveHybridJoinFromValues"/>).
+        /// <paramref name="subKeyExists"/> receives an HKLM-relative subkey path and reports
+        /// whether it exists; a throwing probe degrades to <c>false</c>.
+        /// </summary>
+        internal static bool ResolveIsCloudPc(Func<string, bool> subKeyExists)
+        {
+            if (subKeyExists == null) return false;
+
+            try
+            {
+                return subKeyExists(Windows365MarkerKey) && subKeyExists(CmdeServiceKey);
+            }
+            catch
+            {
+                return false;
+            }
+        }
+
+        private static bool SubKeyExists(string subKeyPath)
+        {
+            using (var key = Registry.LocalMachine.OpenSubKey(subKeyPath))
+            {
+                return key != null;
+            }
+        }
+    }
+}

src/Agent/AutopilotMonitor.Agent.V2.Core/Security/SessionRegistrationHelper.cs

@@ -176,6 +176,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Security
                 EnrollmentType = EnrollmentRegistryDetector.DetectEnrollmentType(),
                 IsHybridJoin = EnrollmentRegistryDetector.DetectHybridJoin(),
                 IsSelfDeployingProfile = EnrollmentRegistryDetector.DetectSelfDeployingProfile(),
+                IsCloudPc = CloudPcDetector.DetectIsCloudPc(),
                 // Deliberately stays true even for self-deploying profiles: the WhiteGlove
                 // Part1/Part2 merge paths and existing dashboards key on IsUserDriven;
                 // IsSelfDeployingProfile is the additive classification signal.

src/Agent/AutopilotMonitor.Agent.V2.Core/SignalAdapters/ImeLogTrackerAdapter.cs

@@ -72,7 +72,7 @@ namespace AutopilotMonitor.Agent.V2.Core.SignalAdapters
         private readonly Action<AppPackageState, AppInstallationState, AppInstallationState>? _prevOnAppStateChanged;
         private readonly Action<string>? _prevOnPatternMatched;
         private readonly Action<string>? _prevOnImeAgentVersion;
-        private readonly Action<AppPackageState>? _prevOnDoTelemetryReceived;
+        private readonly Action<AppPackageState, DateTime?>? _prevOnDoTelemetryReceived;
         private readonly Action<ScriptExecutionState>? _prevOnScriptCompleted;
         private readonly Action<ScriptStartedInfo>? _prevOnScriptStarted;
 
@@ -82,7 +82,7 @@ namespace AutopilotMonitor.Agent.V2.Core.SignalAdapters
         private readonly Action<AppPackageState, AppInstallationState, AppInstallationState> _ourOnAppStateChanged;
         private readonly Action<string> _ourOnPatternMatched;
         private readonly Action<string> _ourOnImeAgentVersion;
-        private readonly Action<AppPackageState> _ourOnDoTelemetryReceived;
+        private readonly Action<AppPackageState, DateTime?> _ourOnDoTelemetryReceived;
         private readonly Action<ScriptExecutionState> _ourOnScriptCompleted;
         private readonly Action<ScriptStartedInfo> _ourOnScriptStarted;
 
@@ -242,10 +242,10 @@ namespace AutopilotMonitor.Agent.V2.Core.SignalAdapters
             EmitImeAgentVersion(version);
         }
 
-        private void OnDoTelemetryReceived(AppPackageState app)
+        private void OnDoTelemetryReceived(AppPackageState app, DateTime? sourceTimestampUtc)
         {
-            _prevOnDoTelemetryReceived?.Invoke(app);
-            EmitDoTelemetry(app);
+            _prevOnDoTelemetryReceived?.Invoke(app, sourceTimestampUtc);
+            EmitDoTelemetry(app, sourceTimestampUtc);
         }
 
         private void OnScriptCompleted(ScriptExecutionState script)
@@ -266,7 +266,8 @@ namespace AutopilotMonitor.Agent.V2.Core.SignalAdapters
             EmitAppState(app, oldState, newState);
         internal void TriggerPatternMatchedFromTest(string patternId) => MaybeEmitWhiteGloveSealingPattern(patternId);
         internal void TriggerImeAgentVersionFromTest(string version) => EmitImeAgentVersion(version);
-        internal void TriggerDoTelemetryFromTest(AppPackageState app) => EmitDoTelemetry(app);
+        internal void TriggerDoTelemetryFromTest(AppPackageState app, DateTime? sourceTimestampUtc = null) =>
+            EmitDoTelemetry(app, sourceTimestampUtc);
         internal void TriggerScriptCompletedFromTest(ScriptExecutionState script) => EmitScriptCompleted(script);
         internal void TriggerScriptStartedFromTest(ScriptStartedInfo info) => EmitScriptStarted(info);
 
@@ -876,7 +877,7 @@ namespace AutopilotMonitor.Agent.V2.Core.SignalAdapters
             _logger?.Info($"ImeAdapter: IME agent version detected: {version}");
         }
 
-        private void EmitDoTelemetry(AppPackageState app)
+        private void EmitDoTelemetry(AppPackageState app, DateTime? sourceTimestampUtc)
         {
             if (app == null || string.IsNullOrEmpty(app.Id)) return;
 
@@ -912,11 +913,31 @@ namespace AutopilotMonitor.Agent.V2.Core.SignalAdapters
             var patternId = _tracker.LastMatchedPatternId;
             if (!string.IsNullOrEmpty(patternId)) data["patternId"] = patternId!;
 
-            var now = ResolveOccurredAt(out var derivedFromClock, out var rawSourceTs);
+            // Two trigger paths with different time grounding (session df1fcf47: a single
+            // tz-skewed unrelated log line inherited via LastMatchedLogTimestamp dragged the
+            // session StartedAt back 7h and inflated the reported duration):
+            //  - [DO TEL] log line (sourceTimestampUtc set): the line's own timestamp is the
+            //    event time — resolve/clamp it and apply historic-replay suppression.
+            //  - DO collector poll (sourceTimestampUtc null): the completion was observed live
+            //    via Get-DeliveryOptimizationStatus; no log line is involved, so the clock is
+            //    the only honest source. LastMatchedLogTimestamp must NOT be consulted here.
+            DateTime now;
+            bool derivedFromClock;
+            DateTime? rawSourceTs;
+            if (sourceTimestampUtc.HasValue)
+            {
+                now = ResolveOccurredAt(sourceTimestampUtc, out derivedFromClock, out rawSourceTs);
 
-            // Historic replay — a week-old DO summary is not this enrollment's download.
-            if (SuppressIfHistoricReplay(derivedFromClock, rawSourceTs, SharedEventTypes.DoTelemetry, app.Id))
-                return;
+                // Historic replay — a week-old DO summary is not this enrollment's download.
+                if (SuppressIfHistoricReplay(derivedFromClock, rawSourceTs, SharedEventTypes.DoTelemetry, app.Id))
+                    return;
+            }
+            else
+            {
+                now = _clock.UtcNow;
+                derivedFromClock = true;
+                rawSourceTs = null;
+            }
 
             TagDerivedTimestamp(data, derivedFromClock, rawSourceTs);
 

src/Agent/AutopilotMonitor.Agent.V2.Core/Telemetry/Events/EventTimelineEmitter.cs

@@ -81,10 +81,12 @@ namespace AutopilotMonitor.Agent.V2.Core.Telemetry.Events
         internal const string ReasonParamKey = "reason";
 
         private readonly TelemetryEventEmitter _emitter;
+        private readonly TimelineEventStream? _timelineEvents;
 
-        public EventTimelineEmitter(TelemetryEventEmitter emitter)
+        public EventTimelineEmitter(TelemetryEventEmitter emitter, TimelineEventStream? timelineEvents = null)
         {
             _emitter = emitter ?? throw new ArgumentNullException(nameof(emitter));
+            _timelineEvents = timelineEvents;
         }
 
         public void Emit(
@@ -142,6 +144,11 @@ namespace AutopilotMonitor.Agent.V2.Core.Telemetry.Events
             };
 
             _emitter.Emit(evt);
+
+            // Post-reduce observer surface: published AFTER the transport enqueue so subscribers
+            // (gather-rule phase/event triggers) see exactly the ordering that reaches the wire.
+            // Publish never throws (subscriber isolation inside the stream).
+            _timelineEvents?.Publish(evt.EventType, evt.Phase);
         }
 
         /// <summary>

src/Agent/AutopilotMonitor.Agent.V2.Core/Termination/EnrollmentTerminationHandler.cs

@@ -39,8 +39,11 @@ namespace AutopilotMonitor.Agent.V2.Core.Termination
     ///     <see cref="SessionStage.WhiteGloveSealed"/> (Part-1 exit, session resumes Part 2).</item>
     ///   <item>WhiteGlove Part-1 path: stop peripheral collectors first (so their stop-time
     ///     stragglers — e.g. <c>network_bandwidth_estimate</c> — sequence BEFORE the marker),
-    ///     then emit <c>whiteglove_part1_complete</c>, drain spool, and write
-    ///     <c>whiteglove.complete</c> marker via <see cref="SessionIdPersistence.SaveWhiteGloveComplete"/>
+    ///     upload the diagnostics package as a pre-provisioning intermediate (suffix
+    ///     <c>preprov</c>, same mode gating as the terminal path — the seal counts as a
+    ///     success, so <c>OnFailure</c> skips), then emit <c>whiteglove_part1_complete</c>,
+    ///     drain spool, and write <c>whiteglove.complete</c> marker via
+    ///     <see cref="SessionIdPersistence.SaveWhiteGloveComplete"/>
     ///     so Part-2 resume is detected on the next boot.</item>
     ///   <item>Signal the caller-owned shutdown <see cref="ManualResetEventSlim"/>.</item>
     /// </list>
@@ -241,6 +244,18 @@ namespace AutopilotMonitor.Agent.V2.Core.Termination
                     // the full Stop() later is a no-op for the hosts.
                     StopPeripheralCollectorsBestEffort();
 
+                    // V1 parity (restored 2026-07-28) — upload the diagnostics package as a
+                    // pre-provisioning intermediate. Between reseal and user OOBE the device
+                    // may sit boxed for weeks, and if Part 2 never uploads (never runs, or
+                    // OnFailure + success) the Part-1 forensics would be lost to self-destruct.
+                    // No dedicated flag: the existing mode semantics apply — Always uploads,
+                    // OnFailure skips (the seal is a success; a Part-1 failure terminates via
+                    // the regular Failed path below, which uploads), Off does nothing. Must run
+                    // BEFORE the whiteglove_part1_complete emit so diagnostics_* events keep a
+                    // lower sequence than the Part-1/Part-2 boundary marker. Best-effort: a
+                    // reseal-reboot racing the upload just loses the intermediate package.
+                    RunUploadDiagnosticsWithEvents(args, suffixOverride: "preprov");
+
                     EmitEventSafe(new EnrollmentEvent
                     {
                         SessionId = _configuration.SessionId,
@@ -777,7 +792,13 @@ namespace AutopilotMonitor.Agent.V2.Core.Termination
                 StringComparison.Ordinal);
         }
 
-        private void RunUploadDiagnosticsWithEvents(EnrollmentTerminatedEventArgs args)
+        /// <param name="args">Termination payload — outcome drives the OnFailure gate.</param>
+        /// <param name="suffixOverride">
+        /// Blob-name suffix override. Null (terminal path) derives "success"/"failure" from
+        /// the outcome; the WhiteGlove Part-1 seal passes "preprov" so the intermediate
+        /// package is distinguishable from the later Part-2 terminal upload.
+        /// </param>
+        private void RunUploadDiagnosticsWithEvents(EnrollmentTerminatedEventArgs args, string suffixOverride = null)
         {
             var mode = _configuration.DiagnosticsUploadMode ?? "Off";
             if (!_configuration.DiagnosticsUploadEnabled || string.Equals(mode, "Off", StringComparison.OrdinalIgnoreCase))
@@ -813,7 +834,7 @@ namespace AutopilotMonitor.Agent.V2.Core.Termination
             DiagnosticsUploadResult result = null;
             try
             {
-                var suffix = enrollmentSucceeded ? "success" : "failure";
+                var suffix = suffixOverride ?? (enrollmentSucceeded ? "success" : "failure");
                 result = _uploadDiagnosticsAsync(enrollmentSucceeded, suffix).GetAwaiter().GetResult();
             }
             catch (Exception ex)

src/Agent/AutopilotMonitor.Agent.V2/Program.GatherRulesMode.cs

@@ -221,8 +221,18 @@ namespace AutopilotMonitor.Agent.V2
                         },
                     });
 
-                    // Step 4 — run the executor and wait.
-                    using (var executor = new GatherRuleExecutor(sessionId, tenantId, emitEvent, logger, config.ImeLogPathOverride))
+                    // Step 4 — run the executor and wait. Diagnostic mode always writes the
+                    // gather-rule debug trace (CLI override or default path) and mirrors it
+                    // to the console in --console mode.
+                    var gatherDebugLogPath = !string.IsNullOrEmpty(config.GatherRuleDebugLogPath)
+                        ? config.GatherRuleDebugLogPath
+                        : Environment.ExpandEnvironmentVariables(Constants.GatherRuleDebugLogPath);
+                    logger.Info($"--run-gather-rules: debug trace -> {gatherDebugLogPath}");
+                    if (consoleMode) Console.WriteLine($"Debug trace: {gatherDebugLogPath}");
+
+                    using (var executor = new GatherRuleExecutor(sessionId, tenantId, emitEvent, logger, config.ImeLogPathOverride,
+                        debugLogPath: gatherDebugLogPath,
+                        debugEcho: consoleMode ? (Action<string>)(line => Console.WriteLine($"  {line}")) : null))
                     {
                         // Diagnostic mode has no enrollment phase context — scoped rules
                         // (activePhases / activeFromPhase) execute unconditionally here.

src/Agent/AutopilotMonitor.Agent.V2/Program.ImeMatchingMode.cs

@@ -6,6 +6,7 @@ using System.Net.Http;
 using System.Text;
 using System.Text.RegularExpressions;
 using AutopilotMonitor.Agent.V2.Core.Monitoring.Enrollment.Ime;
+using AutopilotMonitor.Shared.Logging;
 using AutopilotMonitor.Shared.Models;
 using Newtonsoft.Json;
 

src/Agent/AutopilotMonitor.Agent.V2/Program.cs

@@ -303,6 +303,7 @@ namespace AutopilotMonitor.Agent.V2
             var apiBaseUrl = GetArgValue(args, "--api-url", "--backend-api") ?? Constants.ApiBaseUrl;
             var imeLogPathOverride = GetArgValue(args, "--ime-log-path");
             var imeMatchLogPath = GetArgValue(args, "--ime-match-log");
+            var gatherDebugLogPath = GetArgValue(args, "--gather-debug-log");
 
             // Dev / test — IME log replay (V1 compat mode). Feeds ImeLogTracker.SimulationMode
             // + SpeedFactor so recorded raw IME logs are replayed at an accelerated rate; signal
@@ -373,6 +374,7 @@ namespace AutopilotMonitor.Agent.V2
                 EnableGeoLocation = !disableGeoLocation,
                 ImeLogPathOverride = imeLogPathOverride,
                 ImeMatchLogPath = imeMatchLogPath,
+                GatherRuleDebugLogPath = gatherDebugLogPath,
                 KeepLogFile = keepLogFile,
                 SelfDestructOnComplete = !noCleanup,
                 CommandLineArgs = FormatArgsForLog(args),
@@ -485,6 +487,7 @@ namespace AutopilotMonitor.Agent.V2
             Console.Out.WriteLine("  --api-url <URL>                   Override backend API base URL (alias: --backend-api)");
             Console.Out.WriteLine("  --ime-log-path <PATH>             Override IME logs directory");
             Console.Out.WriteLine("  --ime-match-log <PATH>            Write matched IME log lines to file (debug)");
+            Console.Out.WriteLine("  --gather-debug-log <PATH>         Write gather-rule evaluation trace to file (debug)");
             Console.Out.WriteLine();
             Console.Out.WriteLine("Dev / Test:");
             Console.Out.WriteLine("  --replay-log-dir <PATH>           Replay IME logs from this directory (simulation mode)");

src/Agent/AutopilotMonitor.Agent.V2/Runtime/BackendClientFactory.cs

@@ -102,7 +102,8 @@ namespace AutopilotMonitor.Agent.V2.Runtime
                 serialNumber: hardware.SerialNumber,
                 agentVersion: agentVersion,
                 logger: logger,
-                clientCertificate: clientCertificate);
+                clientCertificate: clientCertificate,
+                isCloudPc: CloudPcDetector.DetectIsCloudPc());
 
             var emergencyReporter = new EmergencyReporter(
                 apiClient: backendApiClient,

src/Agent/AutopilotMonitor.Agent.V2/Runtime/LifecycleEmitters.cs

@@ -309,12 +309,14 @@ namespace AutopilotMonitor.Agent.V2.Runtime
                 var enrollmentType = EnrollmentRegistryDetector.DetectEnrollmentType();
                 var isHybridJoin = EnrollmentRegistryDetector.DetectHybridJoin();
                 var isSelfDeploying = EnrollmentRegistryDetector.DetectSelfDeployingProfile();
+                var isCloudPc = CloudPcDetector.DetectIsCloudPc();
 
                 var payload = new Dictionary<string, string>(StringComparer.Ordinal)
                 {
                     ["enrollmentType"] = enrollmentType,
                     ["isHybridJoin"] = isHybridJoin ? "true" : "false",
                     ["isSelfDeployingProfile"] = isSelfDeploying ? "true" : "false",
+                    ["isCloudPc"] = isCloudPc ? "true" : "false",
                 };
 
                 var evidence = new Evidence(
@@ -329,7 +331,7 @@ namespace AutopilotMonitor.Agent.V2.Runtime
                     evidence: evidence,
                     payload: payload);
 
-                logger.Debug($"EnrollmentFactsObserved signal posted (enrollmentType={enrollmentType}, isHybridJoin={isHybridJoin}, isSelfDeployingProfile={isSelfDeploying}).");
+                logger.Debug($"EnrollmentFactsObserved signal posted (enrollmentType={enrollmentType}, isHybridJoin={isHybridJoin}, isSelfDeployingProfile={isSelfDeploying}, isCloudPc={isCloudPc}).");
             }
             catch (Exception ex)
             {

src/Agent/AutopilotMonitor.Agent.V2/Runtime/ServerControlPlane.cs

@@ -46,8 +46,12 @@ namespace AutopilotMonitor.Agent.V2.Runtime
                     try { var _ = await remoteConfigService.FetchConfigAsync(); return true; }
                     catch (Exception ex) { logger.Warning($"ServerAction rotate_config failed: {ex.Message}"); return false; }
                 },
+                // On-demand request mid-enrollment — the session has no outcome yet. Null keeps
+                // sessioninfo.txt honest ("In Progress") and passes the OnFailure gate by
+                // semantics (there is no success to skip on) instead of the former
+                // enrollmentSucceeded:false workaround that stamped in-flight packages "Failed".
                 uploadDiagnosticsAsync: async (suffix) =>
-                    await diagnosticsService.CreateAndUploadAsync(enrollmentSucceeded: false, fileNameSuffix: suffix),
+                    await diagnosticsService.CreateAndUploadAsync(enrollmentSucceeded: null, fileNameSuffix: suffix),
                 onTerminateRequested: action => OnTerminateRequested(
                     action, agentConfig, orchestrator, terminationHandler, shutdown, shutdownComplete, logger),
                 post: post);

src/Agent/AutopilotMonitor.DecisionCore.Tests/CloudPcObservationTests.cs

@@ -0,0 +1,103 @@
+using System;
+using System.Collections.Generic;
+using AutopilotMonitor.DecisionCore.Engine;
+using AutopilotMonitor.DecisionCore.Signals;
+using AutopilotMonitor.DecisionCore.State;
+using Xunit;
+
+namespace AutopilotMonitor.DecisionCore.Tests
+{
+    /// <summary>
+    /// W365 — reducer-level coverage for the Cloud PC marker fact riding
+    /// <see cref="DecisionSignalKind.EnrollmentFactsObserved"/>: the observation records BOTH
+    /// values set-once (mirror of the registry self-deploying fact), the profile reason
+    /// carries the "no Device-ESP phase expected" expectation, and the signal census folds the
+    /// positive marker into terminal audit trails. The engine deliberately has no DeviceSetup
+    /// arrival requirement, so no behavioural gate is added — the observation is the
+    /// engine-side context that a session starting at Account Setup is the expected shape.
+    /// </summary>
+    public sealed class CloudPcObservationTests
+    {
+        private static readonly DateTime T0 = new DateTime(2026, 8, 7, 10, 0, 0, DateTimeKind.Utc);
+
+        private static DecisionSignal MakeSignal(
+            long ordinal,
+            DecisionSignalKind kind,
+            DateTime occurredAtUtc,
+            IReadOnlyDictionary<string, string>? payload = null) =>
+            new DecisionSignal(
+                sessionSignalOrdinal: ordinal,
+                sessionTraceOrdinal: ordinal,
+                kind: kind,
+                kindSchemaVersion: 1,
+                occurredAtUtc: occurredAtUtc,
+                sourceOrigin: "test",
+                evidence: new Evidence(EvidenceKind.Synthetic, $"t-{kind}-{ordinal}", $"synthetic {kind}"),
+                payload: payload);
+
+        private static DecisionState ReduceFacts(DecisionEngine engine, DecisionState state, long ordinal, string isCloudPc)
+            => engine.Reduce(state, MakeSignal(ordinal, DecisionSignalKind.EnrollmentFactsObserved, T0.AddSeconds(ordinal),
+                new Dictionary<string, string>
+                {
+                    [SignalPayloadKeys.EnrollmentType] = "v1",
+                    [SignalPayloadKeys.IsCloudPc] = isCloudPc,
+                })).NewState;
+
+        [Fact]
+        public void EnrollmentFactsObserved_true_recordsObservation_andExpectationReason()
+        {
+            var engine = new DecisionEngine();
+            var state = engine.Reduce(
+                DecisionState.CreateInitial("cpc-1", "t", T0),
+                MakeSignal(0, DecisionSignalKind.SessionStarted, T0)).NewState;
+
+            state = ReduceFacts(engine, state, 1, "true");
+
+            Assert.NotNull(state.ScenarioObservations.CloudPc);
+            Assert.True(state.ScenarioObservations.CloudPc!.Value);
+            Assert.Equal(1, state.ScenarioObservations.CloudPc!.SourceSignalOrdinal);
+            Assert.Equal(
+                EnrollmentScenarioProfileUpdater.CloudPcNoDeviceEspExpectedReason,
+                state.ScenarioProfile.Reason);
+            // Stage-agnostic fact signal — the reducer must not move the session anywhere.
+            Assert.Equal(SessionStage.SessionStarted, state.Stage);
+        }
+
+        [Fact]
+        public void EnrollmentFactsObserved_false_recordsObservation_setOnce()
+        {
+            var engine = new DecisionEngine();
+            var state = engine.Reduce(
+                DecisionState.CreateInitial("cpc-2", "t", T0),
+                MakeSignal(0, DecisionSignalKind.SessionStarted, T0)).NewState;
+
+            state = ReduceFacts(engine, state, 1, "false");
+            Assert.NotNull(state.ScenarioObservations.CloudPc);
+            Assert.False(state.ScenarioObservations.CloudPc!.Value);
+
+            // Set-once: a later contradicting re-read must not overwrite the first sighting
+            // (same contract as RegistrySelfDeployingProfile — replay-deterministic evidence).
+            state = ReduceFacts(engine, state, 2, "true");
+            Assert.False(state.ScenarioObservations.CloudPc!.Value);
+            Assert.Equal(1, state.ScenarioObservations.CloudPc!.SourceSignalOrdinal);
+        }
+
+        [Fact]
+        public void Census_foldsPositiveMarker_only()
+        {
+            var engine = new DecisionEngine();
+            var initial = engine.Reduce(
+                DecisionState.CreateInitial("cpc-3", "t", T0),
+                MakeSignal(0, DecisionSignalKind.SessionStarted, T0)).NewState;
+
+            var cloudPcState = ReduceFacts(engine, initial, 1, "true");
+            var census = DecisionStateSignalCensus.Build(cloudPcState);
+            Assert.Contains("cloud_pc_marker", census.SignalsSeen);
+            Assert.True(census.SignalEvidence.ContainsKey("cloudPcMarker"));
+
+            var physicalState = ReduceFacts(engine, initial, 1, "false");
+            var physicalCensus = DecisionStateSignalCensus.Build(physicalState);
+            Assert.DoesNotContain("cloud_pc_marker", physicalCensus.SignalsSeen);
+        }
+    }
+}

src/Agent/AutopilotMonitor.DecisionCore.Tests/SerializationTests.cs

@@ -490,7 +490,8 @@ namespace AutopilotMonitor.DecisionCore.Tests
                     .WithShellCoreWhiteGloveSuccessSeen(sourceSignalOrdinal: 3)
                     .WithSkipUserEsp(value: true, sourceSignalOrdinal: 4)
                     .WithEspSyncFailureTimeoutMinutes(value: 90, sourceSignalOrdinal: 5)
-                    .WithRegistrySelfDeployingProfile(value: false, sourceSignalOrdinal: 6))
+                    .WithRegistrySelfDeployingProfile(value: false, sourceSignalOrdinal: 6)
+                    .WithCloudPc(value: true, sourceSignalOrdinal: 7))
                 .Build();
 
             var json = StateSerializer.Serialize(state);
@@ -504,6 +505,8 @@ namespace AutopilotMonitor.DecisionCore.Tests
             Assert.Equal(5, o.EspSyncFailureTimeoutMinutes!.SourceSignalOrdinal);
             Assert.False(o.RegistrySelfDeployingProfile!.Value);
             Assert.Equal(6, o.RegistrySelfDeployingProfile!.SourceSignalOrdinal);
+            Assert.True(o.CloudPc!.Value);
+            Assert.Equal(7, o.CloudPc!.SourceSignalOrdinal);
 
             // Never-observed facts must rehydrate as null (null ≠ veto — session 62e603c9).
             Assert.Null(o.WhiteGloveSealingPatternSeen);

src/Agent/AutopilotMonitor.DecisionCore.Tests/State/EnrollmentScenarioProfileUpdaterTests.cs

@@ -515,6 +515,99 @@ namespace AutopilotMonitor.DecisionCore.Tests.State
 
         // ================================================================== helpers
 
+        // ------------------------------------------------ isCloudPc annotation (W365)
+        // Cloud PC first connect: Device-ESP already ran headless at provisioning, so the
+        // profile records the "no Device-ESP phase expected" expectation as the reason.
+        // Reason-only by design — Mode is classified by AccountSetup/IME signals (Classic),
+        // and EspConfig keeps the CONFIGURED FirstSync semantics.
+
+        [Fact]
+        public void EnrollmentFactsObserved_cloudPc_annotatesReason_keepsModeUnknown()
+        {
+            var signal = MakeSignal(
+                DecisionSignalKind.EnrollmentFactsObserved,
+                ordinal: 0,
+                payload: new Dictionary<string, string>
+                {
+                    [SignalPayloadKeys.EnrollmentType] = "v1",
+                    [SignalPayloadKeys.IsHybridJoin] = "false",
+                    [SignalPayloadKeys.IsCloudPc] = "true",
+                });
+
+            var profile = EnrollmentScenarioProfileUpdater.ApplyEnrollmentFactsObserved(
+                EnrollmentScenarioProfile.Empty, signal);
+
+            Assert.Equal(EnrollmentMode.Unknown, profile.Mode);
+            Assert.Equal(EnrollmentScenarioProfileUpdater.CloudPcNoDeviceEspExpectedReason, profile.Reason);
+            Assert.Equal(EnrollmentJoinMode.AzureAdJoin, profile.JoinMode);
+            Assert.Equal(EspConfig.Unknown, profile.EspConfig);
+        }
+
+        [Fact]
+        public void EnrollmentFactsObserved_cloudPc_repeatPost_isIdempotent()
+        {
+            Dictionary<string, string> Facts() => new Dictionary<string, string>
+            {
+                [SignalPayloadKeys.EnrollmentType] = "v1",
+                [SignalPayloadKeys.IsHybridJoin] = "false",
+                [SignalPayloadKeys.IsCloudPc] = "true",
+            };
+            var first = MakeSignal(DecisionSignalKind.EnrollmentFactsObserved, ordinal: 0, payload: Facts());
+            var second = MakeSignal(DecisionSignalKind.EnrollmentFactsObserved, ordinal: 9, payload: Facts());
+
+            var p1 = EnrollmentScenarioProfileUpdater.ApplyEnrollmentFactsObserved(
+                EnrollmentScenarioProfile.Empty, first);
+            var p2 = EnrollmentScenarioProfileUpdater.ApplyEnrollmentFactsObserved(p1, second);
+
+            // The repeat must be a full no-op: the Cloud PC annotation already owns the
+            // reason slot, and the cloudPcAnnotates gate keeps the generic v1 annotation
+            // from re-claiming it (which would bump EvidenceOrdinal every post).
+            Assert.Same(p1, p2);
+            Assert.Equal(0, p2.EvidenceOrdinal);
+        }
+
+        [Fact]
+        public void EnrollmentFactsObserved_cloudPcFalse_keepsGenericV1Reason()
+        {
+            var signal = MakeSignal(
+                DecisionSignalKind.EnrollmentFactsObserved,
+                ordinal: 0,
+                payload: new Dictionary<string, string>
+                {
+                    [SignalPayloadKeys.EnrollmentType] = "v1",
+                    [SignalPayloadKeys.IsCloudPc] = "false",
+                });
+
+            var profile = EnrollmentScenarioProfileUpdater.ApplyEnrollmentFactsObserved(
+                EnrollmentScenarioProfile.Empty, signal);
+
+            Assert.Equal("enrollment_facts_observed:v1", profile.Reason);
+        }
+
+        [Fact]
+        public void EnrollmentFactsObserved_cloudPc_doesNotDisturbSelfDeployingSeed()
+        {
+            // Defensive combination (not expected in the field — Cloud PCs are never
+            // Autopilot-registered): the deterministic self-deploying Mode seed must
+            // survive; only the reason slot goes to the more specific annotation.
+            var signal = MakeSignal(
+                DecisionSignalKind.EnrollmentFactsObserved,
+                ordinal: 0,
+                payload: new Dictionary<string, string>
+                {
+                    [SignalPayloadKeys.EnrollmentType] = "v1",
+                    [SignalPayloadKeys.IsSelfDeployingProfile] = "true",
+                    [SignalPayloadKeys.IsCloudPc] = "true",
+                });
+
+            var profile = EnrollmentScenarioProfileUpdater.ApplyEnrollmentFactsObserved(
+                EnrollmentScenarioProfile.Empty, signal);
+
+            Assert.Equal(EnrollmentMode.SelfDeploying, profile.Mode);
+            Assert.Equal(ProfileConfidence.High, profile.Confidence);
+            Assert.Equal(EnrollmentScenarioProfileUpdater.CloudPcNoDeviceEspExpectedReason, profile.Reason);
+        }
+
         private static DecisionSignal MakeSignal(
             DecisionSignalKind kind,
             long ordinal,

src/Backend/AutopilotMonitor.Functions.Tests/AdminConfigurationAutoApproveNewTenantsTests.cs

@@ -0,0 +1,34 @@
+using AutopilotMonitor.Shared.Models;
+
+namespace AutopilotMonitor.Functions.Tests;
+
+/// <summary>
+/// Default-value + round-trip tests for <see cref="AdminConfiguration.AutoApproveNewTenants"/>.
+/// The flag gates the tenant auto-approve queue worker — defaulting to false keeps new tenant
+/// signups on manual Global Admin approval until the operator deliberately opts in.
+/// </summary>
+public class AdminConfigurationAutoApproveNewTenantsTests
+{
+    [Fact]
+    public void AutoApproveNewTenants_defaults_to_false_on_new_config()
+    {
+        var cfg = new AdminConfiguration();
+        Assert.False(cfg.AutoApproveNewTenants);
+    }
+
+    [Fact]
+    public void AutoApproveNewTenants_defaults_to_false_on_CreateDefault()
+    {
+        // CreateDefault() is called when no admin-config row exists yet — if it somehow
+        // enabled auto-approve, tenants would activate without any operator opt-in.
+        var cfg = AdminConfiguration.CreateDefault();
+        Assert.False(cfg.AutoApproveNewTenants);
+    }
+
+    [Fact]
+    public void AutoApproveNewTenants_true_persists_on_the_config()
+    {
+        var cfg = new AdminConfiguration { AutoApproveNewTenants = true };
+        Assert.True(cfg.AutoApproveNewTenants);
+    }
+}

src/Backend/AutopilotMonitor.Functions.Tests/AdminConfigurationRateLimitSyncTests.cs

@@ -51,5 +51,7 @@ public class AdminConfigurationRateLimitSyncTests
         // ...but NO tenant configuration is enumerated or mutated (sync removed).
         repo.Verify(r => r.GetAllTenantConfigurationsAsync(), Times.Never);
         repo.Verify(r => r.SaveTenantConfigurationAsync(It.IsAny<TenantConfiguration>()), Times.Never);
+        repo.Verify(r => r.SaveTenantConfigurationAsync(
+            It.IsAny<TenantConfiguration>(), It.IsAny<string?>(), It.IsAny<string?>()), Times.Never);
     }
 }

src/Backend/AutopilotMonitor.Functions.Tests/AdminConfigurationSelfServiceAppHomingTests.cs

@@ -0,0 +1,64 @@
+using AutopilotMonitor.Functions.Services;
+using AutopilotMonitor.Shared.DataAccess;
+using AutopilotMonitor.Shared.Models;
+using Microsoft.Extensions.Caching.Memory;
+using Microsoft.Extensions.Logging.Abstractions;
+using Moq;
+
+namespace AutopilotMonitor.Functions.Tests;
+
+/// <summary>
+/// Default-value + fail-closed tests for <see cref="AdminConfiguration.SelfServiceAppHomingEnabled"/>.
+/// The flag is the kill switch of the dual app-reg self-service homing flip — defaulting to false
+/// keeps the consent funnel and auto-flip off until the operator deliberately opts in, and a
+/// storage error must read as "disabled" (kill switch wins over a blip).
+/// </summary>
+public class AdminConfigurationSelfServiceAppHomingTests
+{
+    [Fact]
+    public void SelfServiceAppHoming_defaults_to_false_on_new_config()
+    {
+        var cfg = new AdminConfiguration();
+        Assert.False(cfg.SelfServiceAppHomingEnabled);
+    }
+
+    [Fact]
+    public void SelfServiceAppHoming_defaults_to_false_on_CreateDefault()
+    {
+        var cfg = AdminConfiguration.CreateDefault();
+        Assert.False(cfg.SelfServiceAppHomingEnabled);
+    }
+
+    [Fact]
+    public void SelfServiceAppHoming_true_persists_on_the_config()
+    {
+        var cfg = new AdminConfiguration { SelfServiceAppHomingEnabled = true };
+        Assert.True(cfg.SelfServiceAppHomingEnabled);
+    }
+
+    [Fact]
+    public async Task Reader_returns_true_when_flag_enabled()
+    {
+        var repo = new Mock<IConfigRepository>();
+        repo.Setup(r => r.GetAdminConfigurationAsync())
+            .ReturnsAsync(new AdminConfiguration { SelfServiceAppHomingEnabled = true });
+        var svc = new AdminConfigurationService(
+            repo.Object, NullLogger<AdminConfigurationService>.Instance,
+            new MemoryCache(new MemoryCacheOptions()));
+
+        Assert.True(await svc.IsSelfServiceAppHomingEnabledAsync());
+    }
+
+    [Fact]
+    public async Task Reader_fails_closed_on_repository_error()
+    {
+        var repo = new Mock<IConfigRepository>();
+        repo.Setup(r => r.GetAdminConfigurationAsync())
+            .ThrowsAsync(new InvalidOperationException("storage down"));
+        var svc = new AdminConfigurationService(
+            repo.Object, NullLogger<AdminConfigurationService>.Instance,
+            new MemoryCache(new MemoryCacheOptions()));
+
+        Assert.False(await svc.IsSelfServiceAppHomingEnabledAsync());
+    }
+}

src/Backend/AutopilotMonitor.Functions.Tests/AnalyzeRuleNotifyTests.cs

@@ -189,7 +189,7 @@ public class AnalyzeRuleNotifyTests
 
         var alert = NotificationAlertBuilder.BuildRuleFiredAlert(
             result, "DESKTOP-CONTOSO1", "SN-1234",
-            "https://portal.autopilotmonitor.com/sessions/abc");
+            "https://portal.autopilotmonitor.com/sessions?id=abc");
 
         Assert.Equal("analyze_rule_fired", alert.EventType);
         Assert.Contains("Proxy blocks enrollment endpoints", alert.Title);
@@ -197,7 +197,7 @@ public class AnalyzeRuleNotifyTests
         Assert.Contains(alert.Facts, f => f.Name == "Serial" && f.Value == "SN-1234");
         Assert.Contains(alert.Facts, f => f.Name == "Rule" && f.Value.Contains("ANALYZE-NET-001"));
         Assert.Contains(alert.Facts, f => f.Name == "Confidence" && f.Value == "85%");
-        Assert.Contains(alert.Actions, a => a.Type == "openUrl" && a.Url == "https://portal.autopilotmonitor.com/sessions/abc");
+        Assert.Contains(alert.Actions, a => a.Type == "openUrl" && a.Url == "https://portal.autopilotmonitor.com/sessions?id=abc");
         Assert.Contains(alert.Sections, s => s.Text.Contains("could not reach"));
     }
 

src/Backend/AutopilotMonitor.Functions.Tests/AppHomingDecisionTests.cs

@@ -0,0 +1,135 @@
+using AutopilotMonitor.Functions.Services;
+
+namespace AutopilotMonitor.Functions.Tests;
+
+/// <summary>
+/// Authorization/validation matrix for <see cref="AppHomingService.EvaluateManualFlip"/> — the
+/// pure decision behind <c>POST config/{tenantId}/app-homing</c>. Contract: tenant admins may
+/// only flip TO primary, without force, with the self-service flag on, and only after a
+/// successful consent probe; Global Admins may flip both directions and force past the probe.
+/// </summary>
+public class AppHomingDecisionTests
+{
+    private static readonly AppHomingProbeResult ProbeOk = new(Succeeded: true, IsTransient: false);
+    private static readonly AppHomingProbeResult ProbeFail = new(Succeeded: false, IsTransient: false);
+    private static readonly AppHomingProbeResult ProbeTransient = new(Succeeded: false, IsTransient: true);
+
+    private static AppHomingDecision Evaluate(
+        bool isGlobalAdmin = false,
+        bool selfServiceEnabled = true,
+        bool legacyConfigured = true,
+        bool currentlyPrimary = false,
+        bool targetPrimary = true,
+        bool force = false,
+        AppHomingProbeResult? probe = null)
+        => AppHomingService.EvaluateManualFlip(
+            isGlobalAdmin, selfServiceEnabled, legacyConfigured, currentlyPrimary, targetPrimary, force, probe);
+
+    [Fact]
+    public void ParallelWindowInactive_denies_for_everyone()
+    {
+        var decision = Evaluate(isGlobalAdmin: true, legacyConfigured: false, force: true);
+        Assert.Equal(AppHomingDecisionKind.Deny, decision.Kind);
+        Assert.Equal("parallel-window-inactive", decision.ReasonCode);
+        Assert.Equal(409, decision.StatusCode);
+    }
+
+    [Theory]
+    [InlineData(false, false)] // legacy-homed, target legacy
+    [InlineData(true, true)]   // primary-homed, target primary
+    public void AlreadyAtTarget_is_a_noop(bool currentlyPrimary, bool targetPrimary)
+    {
+        var decision = Evaluate(currentlyPrimary: currentlyPrimary, targetPrimary: targetPrimary);
+        Assert.Equal(AppHomingDecisionKind.AllowNoOp, decision.Kind);
+    }
+
+    [Fact]
+    public void NonGa_revert_to_legacy_is_denied()
+    {
+        var decision = Evaluate(currentlyPrimary: true, targetPrimary: false);
+        Assert.Equal(AppHomingDecisionKind.Deny, decision.Kind);
+        Assert.Equal("revert-is-ga-only", decision.ReasonCode);
+        Assert.Equal(403, decision.StatusCode);
+    }
+
+    [Fact]
+    public void NonGa_force_is_denied()
+    {
+        var decision = Evaluate(force: true);
+        Assert.Equal(AppHomingDecisionKind.Deny, decision.Kind);
+        Assert.Equal("force-is-ga-only", decision.ReasonCode);
+        Assert.Equal(403, decision.StatusCode);
+    }
+
+    [Fact]
+    public void NonGa_with_flag_off_is_denied()
+    {
+        // The kill switch: turning the admin-config flag off must stop tenant-admin flips
+        // immediately, while the GA path below stays open (operator lever survives).
+        var decision = Evaluate(selfServiceEnabled: false);
+        Assert.Equal(AppHomingDecisionKind.Deny, decision.Kind);
+        Assert.Equal("self-service-disabled", decision.ReasonCode);
+        Assert.Equal(409, decision.StatusCode);
+    }
+
+    [Fact]
+    public void Ga_with_flag_off_still_requires_only_the_probe()
+    {
+        var decision = Evaluate(isGlobalAdmin: true, selfServiceEnabled: false);
+        Assert.Equal(AppHomingDecisionKind.RequireProbe, decision.Kind);
+    }
+
+    [Fact]
+    public void FlipToPrimary_without_probe_requires_probe()
+    {
+        var decision = Evaluate();
+        Assert.Equal(AppHomingDecisionKind.RequireProbe, decision.Kind);
+    }
+
+    [Fact]
+    public void FlipToPrimary_with_successful_probe_is_allowed()
+    {
+        var decision = Evaluate(probe: ProbeOk);
+        Assert.Equal(AppHomingDecisionKind.Allow, decision.Kind);
+    }
+
+    [Fact]
+    public void FlipToPrimary_with_failed_probe_is_denied()
+    {
+        var decision = Evaluate(probe: ProbeFail);
+        Assert.Equal(AppHomingDecisionKind.Deny, decision.Kind);
+        Assert.Equal("probe-failed", decision.ReasonCode);
+        Assert.Equal(409, decision.StatusCode);
+    }
+
+    [Fact]
+    public void FlipToPrimary_with_transient_probe_is_denied_as_retryable()
+    {
+        var decision = Evaluate(probe: ProbeTransient);
+        Assert.Equal(AppHomingDecisionKind.Deny, decision.Kind);
+        Assert.Equal("probe-transient", decision.ReasonCode);
+        Assert.Equal(503, decision.StatusCode);
+    }
+
+    [Fact]
+    public void Ga_flip_without_force_also_requires_probe()
+    {
+        var decision = Evaluate(isGlobalAdmin: true);
+        Assert.Equal(AppHomingDecisionKind.RequireProbe, decision.Kind);
+    }
+
+    [Fact]
+    public void Ga_force_skips_the_probe()
+    {
+        var decision = Evaluate(isGlobalAdmin: true, force: true);
+        Assert.Equal(AppHomingDecisionKind.Allow, decision.Kind);
+    }
+
+    [Fact]
+    public void Ga_revert_to_legacy_needs_no_probe()
+    {
+        // The legacy app is consented by construction — probing it would be meaningless.
+        var decision = Evaluate(isGlobalAdmin: true, currentlyPrimary: true, targetPrimary: false);
+        Assert.Equal(AppHomingDecisionKind.Allow, decision.Kind);
+    }
+}

src/Backend/AutopilotMonitor.Functions.Tests/AppHomingServiceTests.cs

@@ -0,0 +1,289 @@
+using AutopilotMonitor.Functions.Security;
+using AutopilotMonitor.Functions.Services;
+using AutopilotMonitor.Functions.Services.GraphResolution;
+using AutopilotMonitor.Functions.Services.Notifications;
+using AutopilotMonitor.Shared.DataAccess;
+using AutopilotMonitor.Shared.Models;
+using Microsoft.ApplicationInsights;
+using Microsoft.ApplicationInsights.Extensibility;
+using Microsoft.Extensions.Caching.Memory;
+using Microsoft.Extensions.Configuration;
+using Microsoft.Extensions.Logging.Abstractions;
+using Moq;
+
+namespace AutopilotMonitor.Functions.Tests;
+
+/// <summary>
+/// Unit tests for <see cref="AppHomingService"/> — funnel eligibility, the consent-driven
+/// auto-flip, and the flip persist side-effect chain (save + cache invalidation + audit +
+/// ops events). The consent probe and the kill-switch flag are mocked at their virtual seams.
+/// </summary>
+public class AppHomingServiceTests
+{
+    private const string TenantId = "11111111-1111-1111-1111-111111111111";
+    private const string PrimaryId = "aaaaaaaa-0000-0000-0000-000000000001";
+    private const string LegacyId = "bbbbbbbb-0000-0000-0000-000000000002";
+    private const string Actor = "admin@contoso.com";
+
+    private readonly Mock<AdminConfigurationService> _adminConfigMock;
+    private readonly Mock<TenantConfigurationService> _tenantConfigMock;
+    private readonly Mock<GraphTokenService> _graphTokenMock;
+    private readonly Mock<IGraphFeatureDetector> _detectorMock;
+    private readonly Mock<IMaintenanceRepository> _maintenanceMock;
+    private readonly List<OpsEventEntry> _savedOpsEvents = new();
+    private readonly EntraAppRegistry _registry;
+    private readonly AppHomingService _sut;
+
+    public AppHomingServiceTests() : this(legacyConfigured: true) { }
+
+    private AppHomingServiceTests(bool legacyConfigured)
+    {
+        var configValues = new Dictionary<string, string?>
+        {
+            ["EntraId:ClientId"] = PrimaryId,
+            ["EntraId:ClientSecret"] = "primary-secret",
+        };
+        if (legacyConfigured)
+        {
+            configValues["EntraId:LegacyClientId"] = LegacyId;
+            configValues["EntraId:LegacyClientSecret"] = "legacy-secret";
+        }
+        var configuration = new ConfigurationBuilder().AddInMemoryCollection(configValues).Build();
+        _registry = new EntraAppRegistry(configuration, NullLogger<EntraAppRegistry>.Instance);
+
+        var configRepo = Mock.Of<IConfigRepository>();
+        var cache = new MemoryCache(new MemoryCacheOptions());
+
+        _adminConfigMock = new Mock<AdminConfigurationService>(
+            configRepo, NullLogger<AdminConfigurationService>.Instance, cache)
+        { CallBase = false };
+        _tenantConfigMock = new Mock<TenantConfigurationService>(
+            configRepo, NullLogger<TenantConfigurationService>.Instance, cache)
+        { CallBase = false };
+        _graphTokenMock = new Mock<GraphTokenService>(
+            NullLogger<GraphTokenService>.Instance,
+            Mock.Of<System.Net.Http.IHttpClientFactory>(),
+            cache,
+            configuration,
+            _registry,
+            _tenantConfigMock.Object)
+        { CallBase = false };
+        _detectorMock = new Mock<IGraphFeatureDetector>();
+        _maintenanceMock = new Mock<IMaintenanceRepository>();
+        _maintenanceMock
+            .Setup(m => m.LogAuditEntryAsync(It.IsAny<string>(), It.IsAny<string>(), It.IsAny<string>(),
+                It.IsAny<string>(), It.IsAny<string>(), It.IsAny<Dictionary<string, string>?>()))
+            .ReturnsAsync(true);
+
+        var opsRepo = new Mock<IOpsEventRepository>();
+        opsRepo.Setup(r => r.SaveOpsEventAsync(It.IsAny<OpsEventEntry>()))
+            .Callback<OpsEventEntry>(e => { lock (_savedOpsEvents) _savedOpsEvents.Add(e); })
+            .Returns(Task.CompletedTask);
+        var alertDispatch = new OpsAlertDispatchService(
+            _adminConfigMock.Object,
+            new TelegramNotificationService(new HttpClient(), configRepo,
+                NullLogger<TelegramNotificationService>.Instance),
+            new WebhookNotificationService(new HttpClient(),
+                NullLogger<WebhookNotificationService>.Instance),
+            NullLogger<OpsAlertDispatchService>.Instance);
+        var opsService = new OpsEventService(opsRepo.Object, NullLogger<OpsEventService>.Instance, alertDispatch);
+
+        _sut = new AppHomingService(
+            NullLogger<AppHomingService>.Instance,
+            _adminConfigMock.Object,
+            _tenantConfigMock.Object,
+            _registry,
+            _graphTokenMock.Object,
+            _detectorMock.Object,
+            _maintenanceMock.Object,
+            opsService,
+            new TelemetryClient(new TelemetryConfiguration { DisableTelemetry = true }));
+
+        // Defaults: flag on, legacy-homed config exists, probe succeeds. FlipAsync reads via
+        // the cache-bypassing GetConfigurationFreshAsync (read-modify-write on the whole entity).
+        _adminConfigMock.Setup(x => x.IsSelfServiceAppHomingEnabledAsync()).ReturnsAsync(true);
+        var config = LegacyHomedConfig();
+        _tenantConfigMock.Setup(x => x.GetConfigurationFreshAsync(TenantId)).ReturnsAsync(config);
+        _tenantConfigMock.Setup(x => x.SaveConfigurationAsync(It.IsAny<TenantConfiguration>(), It.IsAny<string?>(), It.IsAny<string?>()))
+            .Returns(Task.CompletedTask);
+        SetupProbe(GraphTokenResult.Success("tok"));
+    }
+
+    private static TenantConfiguration LegacyHomedConfig()
+    {
+        var config = TenantConfiguration.CreateDefault(TenantId);
+        config.HomedAppClientId = null;
+        return config;
+    }
+
+    private void SetupProbe(GraphTokenResult result) =>
+        _graphTokenMock
+            .Setup(x => x.GetAccessTokenForAppAsync(TenantId, It.Is<EntraAppCredentials>(c => !c.IsLegacy),
+                It.IsAny<CancellationToken>()))
+            .ReturnsAsync(result);
+
+    // ── IsFunnelEligibleAsync ───────────────────────────────────────────────
+
+    [Fact]
+    public async Task Funnel_is_eligible_for_legacy_homed_tenant_with_flag_on()
+    {
+        Assert.True(await _sut.IsFunnelEligibleAsync(LegacyHomedConfig()));
+    }
+
+    [Fact]
+    public async Task Funnel_is_not_eligible_when_legacy_pair_unconfigured()
+    {
+        var sut = new AppHomingServiceTests(legacyConfigured: false)._sut;
+        Assert.False(await sut.IsFunnelEligibleAsync(LegacyHomedConfig()));
+    }
+
+    [Fact]
+    public async Task Funnel_is_not_eligible_for_primary_homed_tenant()
+    {
+        var config = LegacyHomedConfig();
+        config.HomedAppClientId = PrimaryId;
+        Assert.False(await _sut.IsFunnelEligibleAsync(config));
+    }
+
+    [Fact]
+    public async Task Funnel_is_not_eligible_when_flag_off()
+    {
+        _adminConfigMock.Setup(x => x.IsSelfServiceAppHomingEnabledAsync()).ReturnsAsync(false);
+        Assert.False(await _sut.IsFunnelEligibleAsync(LegacyHomedConfig()));
+    }
+
+    [Fact]
+    public async Task Funnel_does_not_block_on_entra_app_roles()
+    {
+        // Deliberate: app-role tenants may flip (operator informs them personally); the
+        // reminder trail is asserted in the flip test below.
+        var config = LegacyHomedConfig();
+        config.EntraAppRolesEnabled = true;
+        Assert.True(await _sut.IsFunnelEligibleAsync(config));
+    }
+
+    // ── TryAutoFlipToPrimaryAsync ───────────────────────────────────────────
+
+    [Fact]
+    public async Task AutoFlip_flips_on_probe_success_with_full_side_effect_chain()
+    {
+        var outcome = await _sut.TryAutoFlipToPrimaryAsync(LegacyHomedConfig(), Actor);
+
+        Assert.Equal(AppHomingAutoFlipOutcome.Flipped, outcome);
+        _tenantConfigMock.Verify(x => x.SaveConfigurationAsync(It.Is<TenantConfiguration>(c =>
+            string.Equals(c.HomedAppClientId, PrimaryId, StringComparison.OrdinalIgnoreCase)
+            && c.UpdatedBy == Actor), It.IsAny<string?>(), It.IsAny<string?>()), Times.Once);
+        _detectorMock.Verify(x => x.InvalidateTenant(TenantId), Times.Once);
+        _maintenanceMock.Verify(m => m.LogAuditEntryAsync(TenantId, "UPDATE", "TenantConfiguration",
+            TenantId, Actor, It.Is<Dictionary<string, string>?>(d =>
+                d != null && d.ContainsKey("HomedAppClientId"))), Times.Once);
+        Assert.Contains(_savedOpsEvents, e => e.EventType == "AppHomingFlipped");
+        Assert.DoesNotContain(_savedOpsEvents, e => e.EventType == "AppHomingFlippedWithEntraRoles");
+    }
+
+    [Fact]
+    public async Task AutoFlip_does_not_flip_on_permanent_probe_failure()
+    {
+        SetupProbe(GraphTokenResult.PermanentFailure());
+
+        var outcome = await _sut.TryAutoFlipToPrimaryAsync(LegacyHomedConfig(), Actor);
+
+        Assert.Equal(AppHomingAutoFlipOutcome.ProbeFailed, outcome);
+        _tenantConfigMock.Verify(x => x.SaveConfigurationAsync(It.IsAny<TenantConfiguration>(), It.IsAny<string?>(), It.IsAny<string?>()), Times.Never);
+    }
+
+    [Fact]
+    public async Task AutoFlip_does_not_flip_on_transient_probe()
+    {
+        SetupProbe(GraphTokenResult.TransientFailure());
+
+        var outcome = await _sut.TryAutoFlipToPrimaryAsync(LegacyHomedConfig(), Actor);
+
+        Assert.Equal(AppHomingAutoFlipOutcome.ProbeTransient, outcome);
+        _tenantConfigMock.Verify(x => x.SaveConfigurationAsync(It.IsAny<TenantConfiguration>(), It.IsAny<string?>(), It.IsAny<string?>()), Times.Never);
+    }
+
+    [Fact]
+    public async Task AutoFlip_is_not_eligible_for_primary_homed_tenant_and_never_probes()
+    {
+        var config = LegacyHomedConfig();
+        config.HomedAppClientId = PrimaryId;
+
+        var outcome = await _sut.TryAutoFlipToPrimaryAsync(config, Actor);
+
+        Assert.Equal(AppHomingAutoFlipOutcome.NotEligible, outcome);
+        _graphTokenMock.Verify(x => x.GetAccessTokenForAppAsync(It.IsAny<string>(),
+            It.IsAny<EntraAppCredentials>(), It.IsAny<CancellationToken>()), Times.Never);
+    }
+
+    [Fact]
+    public async Task AutoFlip_is_not_eligible_when_flag_off()
+    {
+        _adminConfigMock.Setup(x => x.IsSelfServiceAppHomingEnabledAsync()).ReturnsAsync(false);
+
+        var outcome = await _sut.TryAutoFlipToPrimaryAsync(LegacyHomedConfig(), Actor);
+
+        Assert.Equal(AppHomingAutoFlipOutcome.NotEligible, outcome);
+        _tenantConfigMock.Verify(x => x.SaveConfigurationAsync(It.IsAny<TenantConfiguration>(), It.IsAny<string?>(), It.IsAny<string?>()), Times.Never);
+    }
+
+    // ── FlipAsync ───────────────────────────────────────────────────────────
+
+    [Fact]
+    public async Task Flip_of_entra_app_roles_tenant_emits_reminder_ops_event()
+    {
+        var config = LegacyHomedConfig();
+        config.EntraAppRolesEnabled = true;
+        _tenantConfigMock.Setup(x => x.GetConfigurationFreshAsync(TenantId)).ReturnsAsync(config);
+
+        await _sut.FlipAsync(TenantId, PrimaryId, Actor, "manual-ga");
+
+        Assert.Contains(_savedOpsEvents, e => e.EventType == "AppHomingFlipped");
+        Assert.Contains(_savedOpsEvents, e => e.EventType == "AppHomingFlippedWithEntraRoles");
+    }
+
+    [Fact]
+    public async Task Flip_noops_when_already_at_target()
+    {
+        var config = LegacyHomedConfig();
+        config.HomedAppClientId = PrimaryId;
+        _tenantConfigMock.Setup(x => x.GetConfigurationFreshAsync(TenantId)).ReturnsAsync(config);
+
+        await _sut.FlipAsync(TenantId, PrimaryId, Actor, "manual-ga");
+
+        _tenantConfigMock.Verify(x => x.SaveConfigurationAsync(It.IsAny<TenantConfiguration>(), It.IsAny<string?>(), It.IsAny<string?>()), Times.Never);
+        _detectorMock.Verify(x => x.InvalidateTenant(It.IsAny<string>()), Times.Never);
+        Assert.Empty(_savedOpsEvents);
+    }
+
+    [Fact]
+    public async Task Flip_throws_when_config_row_missing_and_saves_nothing()
+    {
+        // A flip must never materialize a default row (e.g. resurrect an offboarded tenant);
+        // the fresh read returning null is a hard stop.
+        _tenantConfigMock.Setup(x => x.GetConfigurationFreshAsync(TenantId))
+            .ReturnsAsync((TenantConfiguration?)null);
+
+        await Assert.ThrowsAsync<InvalidOperationException>(
+            () => _sut.FlipAsync(TenantId, PrimaryId, Actor, "manual-ga"));
+
+        _tenantConfigMock.Verify(x => x.SaveConfigurationAsync(It.IsAny<TenantConfiguration>(), It.IsAny<string?>(), It.IsAny<string?>()), Times.Never);
+        _detectorMock.Verify(x => x.InvalidateTenant(It.IsAny<string>()), Times.Never);
+        Assert.Empty(_savedOpsEvents);
+    }
+
+    [Fact]
+    public async Task Flip_back_to_legacy_persists_null_homing()
+    {
+        var config = LegacyHomedConfig();
+        config.HomedAppClientId = PrimaryId;
+        _tenantConfigMock.Setup(x => x.GetConfigurationFreshAsync(TenantId)).ReturnsAsync(config);
+
+        await _sut.FlipAsync(TenantId, null, Actor, "manual-ga");
+
+        // The null-homing invariant: legacy is represented as null, never as the legacy GUID.
+        _tenantConfigMock.Verify(x => x.SaveConfigurationAsync(It.Is<TenantConfiguration>(c =>
+            c.HomedAppClientId == null), It.IsAny<string?>(), It.IsAny<string?>()), Times.Once);
+        _detectorMock.Verify(x => x.InvalidateTenant(TenantId), Times.Once);
+    }
+}

src/Backend/AutopilotMonitor.Functions.Tests/AuthFunctionSideEffectTests.cs

@@ -24,6 +24,7 @@ public class AuthFunctionSideEffectTests
     private readonly Mock<TelegramNotificationService> _telegramMock;
     private readonly Mock<GlobalNotificationService> _globalNotificationMock;
     private readonly Mock<IMetricsRepository> _metricsRepoMock;
+    private readonly Mock<AutopilotMonitor.Functions.Services.Activation.ITenantAutoApproveEnqueuer> _autoApproveEnqueuerMock;
     private readonly AuthFunction _sut;
 
     public AuthFunctionSideEffectTests()
@@ -44,7 +45,7 @@ public class AuthFunctionSideEffectTests
 
         var delegatedAdminMock = new Mock<DelegatedAdminService>(
             adminRepo,
-            new StubTenantEntitlementService(AutopilotMonitor.Functions.Security.TenantEdition.Enterprise),
+            new StubTenantEntitlementService(AutopilotMonitor.Functions.Security.TenantEdition.Pro),
             cache, Mock.Of<ILogger<DelegatedAdminService>>())
         { CallBase = false };
         delegatedAdminMock.Setup(x => x.GetScopeAsync(It.IsAny<string>(), It.IsAny<string?>()))
@@ -76,6 +77,7 @@ public class AuthFunctionSideEffectTests
         { CallBase = false };
 
         _metricsRepoMock = new Mock<IMetricsRepository>();
+        _autoApproveEnqueuerMock = new Mock<AutopilotMonitor.Functions.Services.Activation.ITenantAutoApproveEnqueuer>();
 
         _sut = new AuthFunction(
             Mock.Of<ILogger<AuthFunction>>(),
@@ -87,11 +89,15 @@ public class AuthFunctionSideEffectTests
             previewMock.Object,
             _telegramMock.Object,
             _globalNotificationMock.Object,
-            mcpUserMock.Object);
+            mcpUserMock.Object,
+            _autoApproveEnqueuerMock.Object,
+            new AutopilotMonitor.Functions.Security.EntraAppRegistry(
+                new Microsoft.Extensions.Configuration.ConfigurationBuilder().Build(),
+                Mock.Of<ILogger<AutopilotMonitor.Functions.Security.EntraAppRegistry>>()));
 
         // Default: all fire-and-forget calls succeed
         _tenantConfigMock
-            .Setup(x => x.SaveConfigurationAsync(It.IsAny<TenantConfiguration>()))
+            .Setup(x => x.SaveConfigurationAsync(It.IsAny<TenantConfiguration>(), It.IsAny<string?>(), It.IsAny<string?>()))
             .Returns(Task.CompletedTask);
         _telegramMock
             .Setup(x => x.SendNewTenantSignupAsync(It.IsAny<string>(), It.IsAny<string>()))
@@ -126,12 +132,89 @@ public class AuthFunctionSideEffectTests
         // OnboardedBy is the immutable copy of the first-login UPN that auto-promote on
         // preview approval reads — UpdatedBy may later be clobbered by background syncs.
         Assert.Equal(Upn, config.OnboardedBy);
-        _tenantConfigMock.Verify(x => x.SaveConfigurationAsync(config), Times.Once);
+        _tenantConfigMock.Verify(x => x.SaveConfigurationAsync(config, It.IsAny<string?>(), It.IsAny<string?>()), Times.Once);
         _telegramMock.Verify(x => x.SendNewTenantSignupAsync(TenantId, Upn), Times.Once);
         _globalNotificationMock.Verify(x => x.CreateNotificationAsync(
-            "preview_signup", "New Preview Signup",
+            "preview_signup", "New Tenant Signup",
             It.Is<string>(m => m.Contains(TenantId) && m.Contains("contoso.com") && m.Contains(Upn)),
-            null), Times.Once);
+            $"/admin/tenants/management?tenantId={TenantId}"), Times.Once);
+        // Signup enqueues the delayed auto-approve unconditionally — the worker is the
+        // decision point (flag check at processing time).
+        _autoApproveEnqueuerMock.Verify(x => x.EnqueueAsync(
+            It.Is<AutopilotMonitor.Functions.Services.Activation.TenantAutoApproveEnvelope>(
+                e => e.TenantId == TenantId && e.SignupUpn == Upn),
+            AutopilotMonitor.Functions.Services.Activation.TenantAutoApproveEnvelope.ActivationDelay,
+            It.IsAny<CancellationToken>()), Times.Once);
+    }
+
+    // -------------------------------------------------------------------------
+    // HandleAuthClientIdTrackingAsync — the write must mutate a cache-BYPASSING
+    // read, never the (possibly stale) cached view. Regression for the prod
+    // incident 2026-07-31: the login right after an app-homing flip carries the
+    // changed audience; blind-saving the stale cached entity reverted the flip.
+    // -------------------------------------------------------------------------
+
+    private const string LegacyAppId = "1a400946-62c1-4ab4-aa37-f730ac89704d";
+    private const string PrimaryAppId = "886ab5e2-6144-442c-80cc-9b28e0667731";
+
+    [Fact]
+    public async Task HandleAuthClientIdTracking_MutatesFreshConfig_PreservingConcurrentHomingFlip()
+    {
+        // Cached view: pre-flip (homing null, last-seen legacy). Fresh row: flipped meanwhile.
+        var cached = DefaultConfig();
+        cached.DomainName = "contoso.com";
+        cached.LastAuthClientId = LegacyAppId;
+        cached.HomedAppClientId = null;
+
+        var fresh = DefaultConfig();
+        fresh.DomainName = "contoso.com";
+        fresh.LastAuthClientId = LegacyAppId;
+        fresh.HomedAppClientId = PrimaryAppId; // the concurrent flip that must survive
+
+        _tenantConfigMock.Setup(x => x.GetConfigurationFreshAsync(TenantId)).ReturnsAsync(fresh);
+
+        await _sut.HandleAuthClientIdTrackingAsync(cached, TenantId, $"api://{PrimaryAppId}");
+
+        // The FRESH entity was mutated and saved — the flip survives, the stale view is discarded.
+        _tenantConfigMock.Verify(x => x.SaveConfigurationAsync(fresh, It.IsAny<string?>(), It.IsAny<string?>()), Times.Once);
+        _tenantConfigMock.Verify(x => x.SaveConfigurationAsync(cached, It.IsAny<string?>(), It.IsAny<string?>()), Times.Never);
+        Assert.Equal(PrimaryAppId, fresh.HomedAppClientId);
+        Assert.Equal(PrimaryAppId, fresh.LastAuthClientId);
+        Assert.NotNull(fresh.LastAuthClientIdSince);
+    }
+
+    [Fact]
+    public async Task HandleAuthClientIdTracking_FreshAlreadyCurrent_DoesNotWrite()
+    {
+        // Another instance already recorded the new client id — the fresh re-check must
+        // suppress the redundant write even though the cached view still looks outdated.
+        var cached = DefaultConfig();
+        cached.DomainName = "contoso.com";
+        cached.LastAuthClientId = LegacyAppId;
+
+        var fresh = DefaultConfig();
+        fresh.DomainName = "contoso.com";
+        fresh.LastAuthClientId = PrimaryAppId;
+
+        _tenantConfigMock.Setup(x => x.GetConfigurationFreshAsync(TenantId)).ReturnsAsync(fresh);
+
+        await _sut.HandleAuthClientIdTrackingAsync(cached, TenantId, PrimaryAppId);
+
+        _tenantConfigMock.Verify(x => x.SaveConfigurationAsync(It.IsAny<TenantConfiguration>(), It.IsAny<string?>(), It.IsAny<string?>()), Times.Never);
+    }
+
+    [Fact]
+    public async Task HandleAuthClientIdTracking_UnchangedOnCachedView_SkipsFreshRead()
+    {
+        // Steady state (same app as last time) must stay a zero-I/O no-op.
+        var cached = DefaultConfig();
+        cached.DomainName = "contoso.com";
+        cached.LastAuthClientId = PrimaryAppId;
+
+        await _sut.HandleAuthClientIdTrackingAsync(cached, TenantId, $"api://{PrimaryAppId}");
+
+        _tenantConfigMock.Verify(x => x.GetConfigurationFreshAsync(It.IsAny<string>()), Times.Never);
+        _tenantConfigMock.Verify(x => x.SaveConfigurationAsync(It.IsAny<TenantConfiguration>(), It.IsAny<string?>(), It.IsAny<string?>()), Times.Never);
     }
 
     [Fact]
@@ -156,7 +239,7 @@ public class AuthFunctionSideEffectTests
 
         await _sut.HandleNewTenantDomainAsync(config, TenantId, Upn);
 
-        _tenantConfigMock.Verify(x => x.SaveConfigurationAsync(It.IsAny<TenantConfiguration>()), Times.Never);
+        _tenantConfigMock.Verify(x => x.SaveConfigurationAsync(It.IsAny<TenantConfiguration>(), It.IsAny<string?>(), It.IsAny<string?>()), Times.Never);
         _telegramMock.Verify(x => x.SendNewTenantSignupAsync(It.IsAny<string>(), It.IsAny<string>()), Times.Never);
     }
 
@@ -168,7 +251,7 @@ public class AuthFunctionSideEffectTests
 
         await _sut.HandleNewTenantDomainAsync(config, TenantId, "");
 
-        _tenantConfigMock.Verify(x => x.SaveConfigurationAsync(It.IsAny<TenantConfiguration>()), Times.Never);
+        _tenantConfigMock.Verify(x => x.SaveConfigurationAsync(It.IsAny<TenantConfiguration>(), It.IsAny<string?>(), It.IsAny<string?>()), Times.Never);
     }
 
     [Fact]
@@ -179,7 +262,7 @@ public class AuthFunctionSideEffectTests
 
         await _sut.HandleNewTenantDomainAsync(config, TenantId, "nodomain");
 
-        _tenantConfigMock.Verify(x => x.SaveConfigurationAsync(It.IsAny<TenantConfiguration>()), Times.Never);
+        _tenantConfigMock.Verify(x => x.SaveConfigurationAsync(It.IsAny<TenantConfiguration>(), It.IsAny<string?>(), It.IsAny<string?>()), Times.Never);
     }
 
     [Fact]
@@ -196,7 +279,7 @@ public class AuthFunctionSideEffectTests
         await _sut.HandleNewTenantDomainAsync(config, TenantId, Upn);
 
         // SaveConfig should still have been called before the fire-and-forget
-        _tenantConfigMock.Verify(x => x.SaveConfigurationAsync(config), Times.Once);
+        _tenantConfigMock.Verify(x => x.SaveConfigurationAsync(config, It.IsAny<string?>(), It.IsAny<string?>()), Times.Once);
     }
 
     // -------------------------------------------------------------------------
@@ -217,7 +300,7 @@ public class AuthFunctionSideEffectTests
         Assert.Null(config.DisabledReason);
         Assert.Null(config.DisabledUntil);
         Assert.Equal("System (auto-re-enable)", config.UpdatedBy);
-        _tenantConfigMock.Verify(x => x.SaveConfigurationAsync(config), Times.Once);
+        _tenantConfigMock.Verify(x => x.SaveConfigurationAsync(config, It.IsAny<string?>(), It.IsAny<string?>()), Times.Once);
     }
 
     [Fact]
@@ -230,7 +313,7 @@ public class AuthFunctionSideEffectTests
         await _sut.HandleAutoReEnableAsync(config, TenantId);
 
         Assert.True(config.Disabled);
-        _tenantConfigMock.Verify(x => x.SaveConfigurationAsync(It.IsAny<TenantConfiguration>()), Times.Never);
+        _tenantConfigMock.Verify(x => x.SaveConfigurationAsync(It.IsAny<TenantConfiguration>(), It.IsAny<string?>(), It.IsAny<string?>()), Times.Never);
     }
 
     [Fact]
@@ -241,7 +324,7 @@ public class AuthFunctionSideEffectTests
 
         await _sut.HandleAutoReEnableAsync(config, TenantId);
 
-        _tenantConfigMock.Verify(x => x.SaveConfigurationAsync(It.IsAny<TenantConfiguration>()), Times.Never);
+        _tenantConfigMock.Verify(x => x.SaveConfigurationAsync(It.IsAny<TenantConfiguration>(), It.IsAny<string?>(), It.IsAny<string?>()), Times.Never);
     }
 
     [Fact]
@@ -254,7 +337,7 @@ public class AuthFunctionSideEffectTests
         await _sut.HandleAutoReEnableAsync(config, TenantId);
 
         Assert.True(config.Disabled);
-        _tenantConfigMock.Verify(x => x.SaveConfigurationAsync(It.IsAny<TenantConfiguration>()), Times.Never);
+        _tenantConfigMock.Verify(x => x.SaveConfigurationAsync(It.IsAny<TenantConfiguration>(), It.IsAny<string?>(), It.IsAny<string?>()), Times.Never);
     }
 
     // -------------------------------------------------------------------------

src/Backend/AutopilotMonitor.Functions.Tests/AuthFunctionTests.cs

@@ -223,11 +223,11 @@ public class AuthFunctionTests
     }
 
     // -------------------------------------------------------------------------
-    // Gate 2: Preview Gate
+    // Gate 2: Activation Gate
     // -------------------------------------------------------------------------
 
     [Fact]
-    public void PreviewGate_NotApproved_Returns403PrivatePreview()
+    public void PreviewGate_NotApproved_Returns403PendingActivation()
     {
         var result = AuthFunction.BuildAuthResult(
             DefaultConfig(), isGlobalAdmin: false, isGlobalReader: false, isPreviewApproved: false,
@@ -238,7 +238,7 @@ public class AuthFunctionTests
         Assert.False(result.IsSuccess);
         Assert.Equal(HttpStatusCode.Forbidden, result.StatusCode);
         var body = ToDynamic(result.Body);
-        Assert.Equal("PrivatePreview", (string)body.error);
+        Assert.Equal("PendingActivation", (string)body.error);
     }
 
     [Fact]

src/Backend/AutopilotMonitor.Functions.Tests/AuthenticationMiddlewareTokenValidationTests.cs

@@ -203,6 +203,38 @@ public class AuthenticationMiddlewareTokenValidationTests
             Mint(RsaCreds, audience: "api://some-third-app"), ClientId, SecondaryClientId));
     }
 
+    // ── Dual app-reg window (C4A8 move): primary=new app, legacy=old app via LegacyClientId ──
+    // The middleware folds EntraId:LegacyClientId into the additional-id set via
+    // CombineAdditionalClientIdSources, so both apps' tokens validate in bare AND api:// form.
+
+    private const string NewAppId = "886ab5e2-6144-442c-80cc-9b28e0667731";
+    private const string OldAppId = "1a400946-62c1-4ab4-aa37-f730ac89704d";
+
+    [Theory]
+    [InlineData(NewAppId)]
+    [InlineData("api://" + NewAppId)]
+    [InlineData(OldAppId)]
+    [InlineData("api://" + OldAppId)]
+    public void DualAppWindow_accepts_both_apps_tokens_in_both_audience_forms(string audience)
+    {
+        var clientIds = AuthenticationMiddleware.ResolveConfiguredClientIds(
+            NewAppId,
+            AuthenticationMiddleware.CombineAdditionalClientIdSources(OldAppId, null),
+            out _);
+
+        Assert.NotNull(ValidateWith(Mint(RsaCreds, audience: audience), clientIds));
+    }
+
+    [Fact]
+    public void CombineAdditionalClientIdSources_joins_and_skips_empty_sources()
+    {
+        Assert.Equal($"{OldAppId},{SecondaryClientId}",
+            AuthenticationMiddleware.CombineAdditionalClientIdSources(OldAppId, SecondaryClientId));
+        Assert.Equal(OldAppId,
+            AuthenticationMiddleware.CombineAdditionalClientIdSources($"  {OldAppId} ", null, ""));
+        Assert.Null(AuthenticationMiddleware.CombineAdditionalClientIdSources(null, "", "   "));
+    }
+
     // ── BuildValidAudiences: id → {id, api://id}, deduped, empties dropped ────────────────
 
     [Fact]