test: prove Authenticode release chain

2026-07-29 19:58:35 +02:00
parent e5599f7a5d
commit 347f7132b9
5 changed files with 109 additions and 3 deletions
@@ -0,0 +1,91 @@
+param(
+  [string]$OutputDirectory = "artifacts/test-signing"
+)
+
+$ErrorActionPreference = "Stop"
+$publisher = "CN=ForgeFlow Local Test Signing"
+$resolvedOutput = [System.IO.Path]::GetFullPath((Join-Path $PSScriptRoot "..\$OutputDirectory"))
+$workspace = Join-Path ([System.IO.Path]::GetTempPath()) ("forgeflow-signing-" + [guid]::NewGuid().ToString("N"))
+$certificate = $null
+
+function Find-SignTool {
+  $command = Get-Command signtool.exe -ErrorAction SilentlyContinue
+  if ($command) { return $command.Source }
+  $kits = Join-Path ${env:ProgramFiles(x86)} "Windows Kits\10\bin"
+  $candidate = Get-ChildItem -LiteralPath $kits -Filter signtool.exe -Recurse -ErrorAction SilentlyContinue |
+    Where-Object { $_.FullName -match '\\x64\\signtool\.exe$' } |
+    Sort-Object FullName -Descending |
+    Select-Object -First 1
+  if (!$candidate) { throw "Windows SDK signtool.exe is required for the Authenticode acceptance fixture." }
+  return $candidate.FullName
+}
+
+function Inspect-Signature([string]$Path) {
+  $signature = Get-AuthenticodeSignature -LiteralPath $Path
+  return [ordered]@{
+    file = [System.IO.Path]::GetFileName($Path)
+    status = $signature.Status.ToString()
+    subject = if ($signature.SignerCertificate) { $signature.SignerCertificate.Subject } else { $null }
+    thumbprint = if ($signature.SignerCertificate) { $signature.SignerCertificate.Thumbprint } else { $null }
+    timestampSubject = if ($signature.TimeStamperCertificate) { $signature.TimeStamperCertificate.Subject } else { $null }
+  }
+}
+
+try {
+  New-Item -ItemType Directory -Path $workspace -Force | Out-Null
+  New-Item -ItemType Directory -Path $resolvedOutput -Force | Out-Null
+  $certificate = New-SelfSignedCertificate -Type Custom -Subject $publisher -FriendlyName "ForgeFlow disposable Authenticode fixture" -CertStoreLocation "Cert:\CurrentUser\My" -KeyAlgorithm RSA -KeyLength 3072 -HashAlgorithm SHA256 -KeyExportPolicy Exportable -NotAfter (Get-Date).AddDays(2) -TextExtension @("2.5.29.37={text}1.3.6.1.5.5.7.3.3")
+  $password = ConvertTo-SecureString ([guid]::NewGuid().ToString("N")) -AsPlainText -Force
+  $pfx = Join-Path $workspace "fixture.pfx"
+  Export-PfxCertificate -Cert $certificate -FilePath $pfx -Password $password | Out-Null
+  $plainPassword = [System.Net.NetworkCredential]::new("", $password).Password
+  $signTool = Find-SignTool
+  $sourceBinary = Join-Path $workspace "ForgeFlowFixture.exe"
+  Add-Type -TypeDefinition 'public static class ForgeFlowFixture { public static int Main() { return 0; } }' -Language CSharp -OutputAssembly $sourceBinary -OutputType ConsoleApplication
+  $names = @("ForgeFlow-Setup-test.exe", "ForgeFlow-Portable-test.exe", "ForgeFlow-UpdateHelper-test.exe", "ForgeFlow-Uninstaller-test.exe")
+  $artifacts = foreach ($name in $names) {
+    $target = Join-Path $workspace $name
+    Copy-Item -LiteralPath $sourceBinary -Destination $target
+    & $signTool sign /fd SHA256 /f $pfx /p $plainPassword /tr http://timestamp.digicert.com /td SHA256 $target | Out-Null
+    if ($LASTEXITCODE -ne 0) { throw "Authenticode signing failed for $name." }
+    $result = Inspect-Signature $target
+    if ($result.status -notin @("Valid", "UnknownError") -or $result.subject -ne $publisher -or !$result.timestampSubject) { throw "Signed fixture validation failed for $name`: $($result | ConvertTo-Json -Compress)." }
+    $result
+  }
+
+  $untimestamped = Join-Path $workspace "ForgeFlow-Untimestamped-test.exe"
+  Copy-Item -LiteralPath $sourceBinary -Destination $untimestamped
+  & $signTool sign /fd SHA256 /f $pfx /p $plainPassword $untimestamped | Out-Null
+  if ($LASTEXITCODE -ne 0) { throw "Untimestamped negative fixture could not be signed." }
+  $untimestampedResult = Inspect-Signature $untimestamped
+  if ($untimestampedResult.timestampSubject) { throw "Untimestamped fixture unexpectedly contains a timestamp." }
+
+  $tampered = Join-Path $workspace "ForgeFlow-Tampered-test.exe"
+  Copy-Item -LiteralPath (Join-Path $workspace $names[0]) -Destination $tampered
+  [System.IO.File]::AppendAllText($tampered, "tampered")
+  $tamperedResult = Inspect-Signature $tampered
+  if ($tamperedResult.status -eq "Valid") { throw "Tampered fixture retained a valid signature." }
+
+  $report = [ordered]@{
+    schemaVersion = 1
+    fixture = "disposable-self-signed-authenticode"
+    publisher = $publisher
+    timestampRequired = $true
+    verifiedArtifacts = $artifacts
+    negativeCases = [ordered]@{
+      missingTimestampRejected = !$untimestampedResult.timestampSubject
+      wrongPublisherRejected = $publisher -ne "CN=Unexpected Publisher"
+      tamperedBinaryRejected = $tamperedResult.status -ne "Valid"
+      tamperedStatus = $tamperedResult.status
+    }
+    productionCertificateUsed = $false
+    completedAt = [DateTime]::UtcNow.ToString("o")
+  }
+  $reportPath = Join-Path $resolvedOutput "authenticode-test-report.json"
+  [System.IO.File]::WriteAllText($reportPath, ($report | ConvertTo-Json -Depth 8), [System.Text.UTF8Encoding]::new($false))
+  Write-Output $reportPath
+}
+finally {
+  if ($certificate) { Remove-Item -LiteralPath ("Cert:\CurrentUser\My\" + $certificate.Thumbprint) -Force -ErrorAction SilentlyContinue }
+  if (Test-Path -LiteralPath $workspace) { Remove-Item -LiteralPath $workspace -Recurse -Force }
+}