Files
AutopilotMonitor/scripts/Bootstrap/Start-AutopilotMonitor.Tests.ps1
T
Oliver Kieselbach 0ac548bfce feat(bootstrap): two-stage loader and Authenticode-signed customer scripts (D-224)
Start-AutopilotMonitor.ps1 is the new stage 1 -- the file an administrator assigns in
Intune. It carries no enrollment logic: it downloads the published installer, verifies its
Authenticode signature, and runs it in the same process, passing through every remaining
argument. Assigning the installer directly stays supported and unchanged.

The point of the split is that the customer-held artifact stops changing. Today every
bootstrap change forces customers to replace their Intune copy, so the fleet runs a
distribution of script versions we do not control. It is also what makes script signing
worth doing: signing a file that gets swapped by hand each release is a one-off gain,
signing a loader that never changes is permanent.

The loader is deliberately minimal, because it is the one piece that cannot be fixed
remotely -- every guard placed in it would be frozen for years. All guards stay in stage 2.

Verification pins the certificate SUBJECT, never a thumbprint: certificates get renewed and
a deployed loader cannot be, so a thumbprint pin would strand the fleet at the next
renewal. A hash oracle was rejected for a different reason -- it would have to be fetched
from the same host as the script, so it could not survive a compromise of that host, while
the expected publisher travels inside the loader.

Fail-closed on verification, fail-soft on exit: nothing runs without a valid signature from
us (running unverified code as SYSTEM is the risk being removed here), but the loader still
exits 0, because a device without monitoring is acceptable and a failed enrollment step is
not. The accepted cost is that a device which can never fetch or verify stays silent.

Publisher changes:

- every published script is signed (loader, installer, both -Dev renders,
  Test-ShouldBootstrapAgent, Grant-AutopilotMonitorAddOn), and signing is the LAST
  transformation: it covers exactly the CRLF/UTF-8 bytes Get-PublishBytes produced, so
  nothing may normalise or re-encode them afterwards.
- signing is mandatory for a real publish. Only -DryRun may run unsigned, because the PR
  gate executes the publisher without any Azure login.
- comparisons against a published copy strip the signature block first. A timestamped
  signature differs on every run, so without stripping the version-bump guard and the
  drift check would report a change for every unchanged script.
- the bump guard became Assert-VersionBump and now covers the loader as well.
- version.json gains loaderVersion. Additive, no consumer yet: stage 2 is current by
  construction, so only stage 1's version says anything about a customer's Intune copy.
- -SignedOutputDir writes the exact uploaded bytes for the CI artifact, in a dry run too --
  that is how a signed script gets inspected before it reaches anyone.

publish-scripts.yml logs in with the signing identity first and only to fetch the Key Vault
token (azure/login sets the default az account and the storage login has to be the one that
stays), then publishes and offers the signed scripts as an artifact. build-agent.yml passes
the same parameters on a stable cutover.

Tests: 14 new Pester cases, including that a validly signed script from a FOREIGN publisher
is refused -- that is what an attacker with any code-signing certificate can produce. Full
bootstrap suite on Windows PowerShell 5.1: 43/43.

Not covered: the MSI runner still downloads stage 2 without verifying it, and the customer
docs still describe the direct assignment only.

Co-Authored-By: Claude Opus 5 (1M context) <noreply@anthropic.com>
2026-09-08 18:48:21 +02:00

128 lines
5.7 KiB
PowerShell

# Pester tests (Pester 5+) for the stage-1 loader Start-AutopilotMonitor.ps1.
#
# The script under test is dot-sourced; its entry guard prevents the loader from
# executing, so loading it here is side-effect free. Network and signature checks
# are mocked -- what is verified is the DECISION: what does the loader accept, what
# does it refuse, and how often does it retry.
#
# 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 $PSScriptRoot 'Start-AutopilotMonitor.ps1')
function New-FakeSignature {
param([string]$Status, [string]$Subject)
$cert = if ($Subject) {
[pscustomobject]@{ Subject = $Subject; Thumbprint = '0123456789ABCDEF' }
} else { $null }
return [pscustomobject]@{ Status = $Status; SignerCertificate = $cert }
}
}
Describe 'Test-BootstrapSignature' {
BeforeEach {
Mock Write-Log { }
}
It 'accepts a valid signature from the expected publisher' {
Mock Get-AuthenticodeSignature { New-FakeSignature -Status 'Valid' -Subject 'CN=glueckkanja AG, O=glueckkanja AG, C=DE' }
Test-BootstrapSignature -Path 'TestDrive:\x.ps1' | Should -BeTrue
}
It 'refuses an unsigned script' {
Mock Get-AuthenticodeSignature { New-FakeSignature -Status 'NotSigned' -Subject $null }
Test-BootstrapSignature -Path 'TestDrive:\x.ps1' | Should -BeFalse
}
It 'refuses a tampered script (hash mismatch)' {
Mock Get-AuthenticodeSignature { New-FakeSignature -Status 'HashMismatch' -Subject 'CN=glueckkanja AG, O=glueckkanja AG, C=DE' }
Test-BootstrapSignature -Path 'TestDrive:\x.ps1' | Should -BeFalse
}
It 'refuses a signature whose chain does not validate' {
Mock Get-AuthenticodeSignature { New-FakeSignature -Status 'UnknownError' -Subject 'CN=glueckkanja AG, O=glueckkanja AG, C=DE' }
Test-BootstrapSignature -Path 'TestDrive:\x.ps1' | Should -BeFalse
}
# The whole point of the pinned publisher: a validly signed script from someone else
# is exactly what an attacker with any code-signing certificate can produce.
It 'refuses a valid signature from a different publisher' {
Mock Get-AuthenticodeSignature { New-FakeSignature -Status 'Valid' -Subject 'CN=Somebody Else, O=Somebody Else Ltd, C=US' }
Test-BootstrapSignature -Path 'TestDrive:\x.ps1' | Should -BeFalse
}
It 'refuses when the signature check itself fails' {
Mock Get-AuthenticodeSignature { throw 'file not found' }
Test-BootstrapSignature -Path 'TestDrive:\x.ps1' | Should -BeFalse
}
}
Describe 'Get-VerifiedBootstrapScript' {
BeforeEach {
Mock Write-Log { }
Mock Start-Sleep { }
Mock Invoke-WebRequest { }
}
It 'returns after the first attempt when the download verifies' {
Mock Test-BootstrapSignature { $true }
Get-VerifiedBootstrapScript -Url 'https://example.invalid/s.ps1' -Destination 'TestDrive:\s.ps1' | Should -BeTrue
Should -Invoke Invoke-WebRequest -Times 1 -Exactly
}
It 'gives up after three attempts when verification keeps failing' {
Mock Test-BootstrapSignature { $false }
Get-VerifiedBootstrapScript -Url 'https://example.invalid/s.ps1' -Destination 'TestDrive:\s.ps1' | Should -BeFalse
Should -Invoke Invoke-WebRequest -Times 3 -Exactly
}
# A truncated or proxy-mangled body fails verification, so the retry has to cover the
# download AND the check, not just the transport.
It 'retries a failed verification and accepts a later attempt' {
$script:calls = 0
Mock Test-BootstrapSignature { $script:calls++; return ($script:calls -ge 2) }
Get-VerifiedBootstrapScript -Url 'https://example.invalid/s.ps1' -Destination 'TestDrive:\s.ps1' | Should -BeTrue
Should -Invoke Invoke-WebRequest -Times 2 -Exactly
}
It 'retries a transport failure' {
$script:downloads = 0
Mock Invoke-WebRequest { $script:downloads++; if ($script:downloads -eq 1) { throw 'connection reset' } }
Mock Test-BootstrapSignature { $true }
Get-VerifiedBootstrapScript -Url 'https://example.invalid/s.ps1' -Destination 'TestDrive:\s.ps1' | Should -BeTrue
Should -Invoke Invoke-WebRequest -Times 2 -Exactly
}
It 'never executes anything when no attempt verifies' {
Mock Test-BootstrapSignature { $false }
Get-VerifiedBootstrapScript -Url 'https://example.invalid/s.ps1' -Destination 'TestDrive:\s.ps1' | Should -BeFalse
}
}
Describe 'publish contract' {
BeforeAll {
$script:loaderText = Get-Content (Join-Path $PSScriptRoot 'Start-AutopilotMonitor.ps1') -Raw
}
# Publish-BootstrapScripts.ps1 renders the -Dev loader by substituting this exact
# literal and fails the publish when it is gone. Catching that here means the PR fails
# instead of the publish.
It 'carries the dev-render anchor the publisher substitutes' {
$anchor = '$BootstrapUrl = "https://download.autopilotmonitor.com/agent/Install-AutopilotMonitor.ps1"'
$script:loaderText.Contains($anchor) | Should -BeTrue
}
# The publisher parses this to write version.json.loaderVersion and to run the
# version-bump guard.
It 'declares a parsable ScriptVersion' {
$script:loaderText -match '\$ScriptVersion\s*=\s*"([\d\.\-a-zA-Z]+)"' | Should -BeTrue
}
It 'pins the expected publisher by subject, not by thumbprint' {
$script:loaderText -match '\$ExpectedPublisher\s*=\s*"\*O=' | Should -BeTrue
}
}