w365: CloudPc device validator — cert-CN-bound fallback for Cloud PCs (#127)

* w365: CloudPc device validator — cert-CN-bound fallback for Cloud PCs

Windows 365 Cloud PCs are never Autopilot-registered, so the serial lookup
(and the Corporate Identifier fallback) structurally reject them and Cloud PC
first-connect enrollment could not be monitored. New stage-3 fallback in the
device-validation chain: extract the Intune device id from the chain-validated
MDM client certificate's Subject CN (field-verified: CN == managedDevice id ==
cloudPC.managedDeviceId) and require a matching cloudPC object in the claimed
tenant (Graph v1.0 virtualEndpoint/cloudPCs, $filter=managedDeviceId eq).
Only service-provisioned Cloud PCs have such an object — a regular enrolled
non-Autopilot device still ends in the 403, and local W365 markers are never
consulted for auth.

- Shared: ValidatorType.CloudPc = 5, TenantConfiguration.ValidateCloudPcDevice
  (default false, tenant-admin writable), GraphAppPermissions.CloudPCReadAll,
  GraphFeatureCatalog feature W365CloudPcValidation -> CloudPC.Read.All
- Backend: CloudPcDeviceValidator (AutopilotDeviceValidator sibling contract:
  30/5 min cache, 2 attempts, transient->503; GUID gate before the OData
  filter; exact-match guard; Graph 403 = definitive "grant missing", not
  transient), SecurityValidator CN extraction + fallback stage + hard gate,
  wiring through the 5 agent endpoints, TableConfigRepository persistence
- Consent script: W365CloudPcValidation in catalog/ValidateSet/help; NEW
  GraphFeatureCatalogSyncTests pins C# catalog <-> grant script (previously
  comment-only lock-step)
- Bootstrap dev script v2.3-dev.3: guard 4 (uptime window) exempted while the
  Cloud-PC relax is active — Cloud PCs run headless for days before first
  connect; the fresh-profile window is the time anchor there (+ Pester tests)
- Web: validation toggle + context plumbing, ValidatedBy "CloudPc" label,
  privacy-page validation claim generalized (Last updated bumped)
- Docs: OKF concept doc backend/cloudpc-device-validation.md + index + log

Verified: web tsc clean, ESLint 0 errors (99 pre-existing warnings = ratchet
cap, none added). .NET build/tests and Pester run in CI — SDK download and
pwsh are unavailable in this sandbox's network policy.

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

* w365: agent-side IsCloudPc flag + engine expectation "no Device-ESP phase"

Companion to the CloudPc validator: the agent now classifies Windows 365
Cloud PCs locally with the bootstrap's field-verified marker AND
(HKLM\SOFTWARE\Microsoft\Windows365 key + installed
CloudManagedDesktopExtension service, probed via its Services registry key
so net48 needs no System.ServiceProcess). SKIP-safe: any error resolves
false. Never an auth input - backend admission stays exclusively the
cert-CN-bound Graph lookup (ValidatedBy=CloudPc); the two signals are
independent and may disagree.

Two transport rails:

- Session metadata: SessionRegistration.IsCloudPc -> Sessions table
  (sticky-true OR across re-registrations, IsSelfDeployingProfile pattern)
  -> SessionsIndex full mirror -> SessionSummary -> new isCloudPc search
  filter end to end (SearchSessions + QueryRawSessions + pagination
  fingerprint + all three in-memory predicates; MCP search_sessions /
  query_raw_sessions params + summary projection; web type, Cloud PC pill,
  SessionInfoCard enrollment label, CSV export appended column).
- Decision engine: isCloudPc rides the EnrollmentFactsObserved payload,
  recorded set-once for BOTH values in EnrollmentScenarioObservations.CloudPc
  and annotates the scenario profile reason
  cloud_pc_first_connect:no_device_esp_expected - the engine-recorded
  expectation that Device-ESP already ran headless at provisioning and the
  session starts at Account Setup. Deliberately reason+observation only:
  no completion arm depends on DeviceSetup, Mode stays AccountSetup/IME-
  classified (Classic), EspConfig keeps configured-FirstSync semantics.
  Positive marker surfaces as cloud_pc_marker in the audit-trail census.
  Updater idempotency: the cloudPcAnnotates gate keeps the generic v1
  reason branch from re-claiming the slot on repeat posts (would bump
  EvidenceOrdinal every post). Additive-nullable observation - no state
  schema bump (v4 convention), serializer roundtrip pinned.

Tests: CloudPcDetector resolver (marker AND, throwing probe), registration
body, facts-signal payload shape, updater annotation/idempotency/
self-deploying interplay, reducer observation both values + census fold,
serializer roundtrip, index projection superset, sticky-true both
directions. Suites: DecisionCore 500, Functions 3941, Agent V2 2154,
vitest 632 - all green; tsc web+MCP clean; ESLint 0 errors (cap 99).

Docs: cloudpc-device-validation.md follow-up section replaced with the
shipped mechanism + log entry.

Co-Authored-By: Claude Fable 5 <noreply@anthropic.com>

---------

Co-authored-by: Claude <noreply@anthropic.com>
This commit is contained in:
Oliver Kieselbach
2026-08-07 12:31:08 +02:00
committed by GitHub
parent 17affb6dfd
commit 1c5f69a9fe
58 changed files with 1534 additions and 43 deletions
@@ -248,6 +248,36 @@ Describe 'Get-BootstrapDecision' {
$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
@@ -45,6 +45,8 @@
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
@@ -63,9 +65,11 @@
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: a Cloud PC may run for days between provisioning and the user's
first connect; this guard then skips INTENTIONALLY -- the enrollment finished
long ago and there is nothing left to monitor.
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 for the relax
@@ -86,6 +90,11 @@
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
@@ -135,7 +144,7 @@ param(
)
# Script version (bump on meaningful changes; see .CHANGELOG above)
$ScriptVersion = "2.3-dev.2"
$ScriptVersion = "2.3-dev.3"
# Configuration - Everything in ProgramData for easy cleanup
$AgentBasePath = "$env:ProgramData\AutopilotMonitor"
@@ -317,14 +326,22 @@ function Get-BootstrapDecision {
# 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 note: uptime may exceed the window when the user first connects days after
# provisioning -> skip is intentional (enrollment finished long ago, nothing to monitor).
# 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."
return [pscustomobject]@{ Install = $false; ReasonCode = 'UptimeExceeded'; RelaxActive = $relax.Active }
if ($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 = $relax.Active }
}
}
# Guard 5: Is the agent already installed? (leftover from previous run)
@@ -23,7 +23,11 @@
One or more high-level feature identifiers. The script translates each to the underlying
Graph permissions. Use this when you don't want to know permission strings.
Available features:
- ScriptDisplayNames -> DeviceManagementScripts.Read.All
- ScriptDisplayNames -> DeviceManagementScripts.Read.All
- W365CloudPcValidation -> CloudPC.Read.All
(validates Windows 365 Cloud PCs against the tenant's Cloud PC inventory --
Cloud PCs are never Autopilot-registered, so this enables agent monitoring
of Cloud PC first-connect enrollment)
.PARAMETER Permissions
Microsoft Graph application permission names to grant directly. Use when the admin UI
@@ -76,7 +80,7 @@ param(
[string]$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.