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Fix intermittent failures in CertificatesObserverTests#3687

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RyAuld merged 1 commit intomasterfrom
fix/certificate-observer-test-intermittent-failures-clean
Jan 29, 2026
Merged

Fix intermittent failures in CertificatesObserverTests#3687
RyAuld merged 1 commit intomasterfrom
fix/certificate-observer-test-intermittent-failures-clean

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@RyAuld RyAuld commented Jan 28, 2026

This PR fixes intermittent test failures in CertificatesObserverTests.ObserverSendsCorrectEvents.

Problem

The test was experiencing intermittent failures that were causing unreliable CI/CD pipeline results due to AADSTS700027 authentication errors.

Root Causes Fixed

1. Certificate Validation Logic Issue

Problem: MockHttpMessageHandler was using object reference comparison for certificate validation.
Fix: Changed to thumbprint-based comparison using StringComparison.OrdinalIgnoreCase.

2. Cross-Framework Test Interference

Problem: Parallel test execution across .NET frameworks caused certificate naming collisions.
Fix: Implemented unique certificate naming with GUID prefixes.

3. Certificate Store Timing Issues

Problem: Certificate store operations had timing inconsistencies.
Fix: Added robust certificate store verification with proper timing controls.

Test Results

✅ Passes consistently across NET 8.0, 9.0, and 10.0 frameworks
✅ Eliminated AADSTS700027 authentication errors
✅ Resolved parallel test execution conflicts
✅ Improved CI/CD pipeline reliability

Files Changed

  • ests/Microsoft.Identity.Web.Test/CertificatesObserverTests.cs - Only file modified

This PR contains only the specific fix for the certificate observer test, with no other changes.

- Fixed certificate validation logic in MockHttpMessageHandler to use thumbprint-based comparison instead of object reference equality
- Added robust certificate store verification with timing controls to handle asynchronous store operations
- Implemented unique certificate naming with GUID prefixes to prevent cross-framework test interference
- Resolved AADSTS700027 authentication errors and parallel test execution conflicts

The test now passes consistently across all target .NET frameworks (8.0, 9.0, 10.0) with reliable certificate handling.
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LGTM

@RyAuld RyAuld merged commit e9e79ae into master Jan 29, 2026
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@RyAuld RyAuld deleted the fix/certificate-observer-test-intermittent-failures-clean branch January 29, 2026 20:12
This was referenced Mar 1, 2026
github-actions bot pushed a commit to EelcoLos/nx-tinkering that referenced this pull request Mar 3, 2026
[//]: # (dependabot-start)
⚠️  **Dependabot is rebasing this PR** ⚠️ 

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---

[//]: # (dependabot-end)

Updated
[Microsoft.Identity.Web](https://github.com/AzureAD/microsoft-identity-web)
from 4.3.0 to 4.4.0.

<details>
<summary>Release notes</summary>

_Sourced from [Microsoft.Identity.Web's
releases](https://github.com/AzureAD/microsoft-identity-web/releases)._

## 4.4.0

### New features
- Add AOT-compatible web API authentication for .NET 10+. See
[#​3705](AzureAD/microsoft-identity-web#3705)
and
[#​3664](AzureAD/microsoft-identity-web#3664).
- Propagate long-running web API session key back to callers in user
token acquisition. See
[#​3728](AzureAD/microsoft-identity-web#3728).
- Add OBO event initialization for OBO APIs. See
[#​3724](AzureAD/microsoft-identity-web#3724).
- Add support for calling `WithClientClaims` flow for token acquisition.
See
[#​3623](AzureAD/microsoft-identity-web#3623).
- Add `OnBeforeTokenAcquisitionForOnBehalfOf` event. See
[#​3680](AzureAD/microsoft-identity-web#3680).

### Bug fixes
- Throw `InvalidOperationException` with actionable message when a
custom credential is not registered. See
[#​3626](AzureAD/microsoft-identity-web#3626).
- Fix event firing for
`InvokeOnBeforeTokenAcquisitionForOnBehalfOfAsync`. See
[#​3717](AzureAD/microsoft-identity-web#3717).
- Update `OnBeforeTokenAcquisitionForOnBehalfOf` to construct
`ClaimsPrincipal` from token. See
[#​3714](AzureAD/microsoft-identity-web#3714).
- Add a retry counter for acquire token and updated tests with a fake
secret. See
[#​3682](AzureAD/microsoft-identity-web#3682).
- Fix OBO user error handling. See
[#​3712](AzureAD/microsoft-identity-web#3712).
- Fix override merging for app token (and others). See
[#​3644](AzureAD/microsoft-identity-web#3644).
- Fix certificate reload logic to only trigger on certificate-specific
errors. See
[#​3653](AzureAD/microsoft-identity-web#3653).
- Update ROPC flow CCA to pass `SendX5C` to MSAL. See
[#​3671](AzureAD/microsoft-identity-web#3671).

### Dependencies updates
- Bump `qs` in `/tests/DevApps/SidecarAdapter/typescript`. See
[#​3725](AzureAD/microsoft-identity-web#3725).
- Downgrade Microsoft.Extensions.Configuration.Binder to 2.1.0 on .NET
Framework. See
[#​3730](AzureAD/microsoft-identity-web#3730).
- Update .NET SDK to 10.0.103 to address DOTNET-Security-10.0
vulnerability. See
[#​3726](AzureAD/microsoft-identity-web#3726).
- Upgrade to Microsoft.Identity.Abstractions 11 for AoT compatibility.
See
[#​3699](AzureAD/microsoft-identity-web#3699).
- Update to MSAL 4.81.0. See
[#​3665](AzureAD/microsoft-identity-web#3665).

### Documentation
- Add documentation for auto-generated session key for long-running OBO
session. See
[#​3729](AzureAD/microsoft-identity-web#3729).
- Improve the Aspire doc article and skills. See
[#​3695](AzureAD/microsoft-identity-web#3695).
- Add an article and agent skill to add Entra ID to an Aspire app. See
[#​3689](AzureAD/microsoft-identity-web#3689).
- Fix misleading comment in
`CertificatelessOptions.ManagedIdentityClientId`. See
[#​3667](AzureAD/microsoft-identity-web#3667).
- Add Copilot explore tool functionality. See
[#​3694](AzureAD/microsoft-identity-web#3694).

### Fundamentals
- Remove unnecessary warning suppression. See
[#​3715](AzureAD/microsoft-identity-web#3715).
- Migrate labs to Lab.API 2.x (first pass). See
[#​3710](AzureAD/microsoft-identity-web#3710).
- Update Sidecar E2E test constants. See
[#​3693](AzureAD/microsoft-identity-web#3693).
- Fix intermittent failures in `CertificatesObserverTests`. See
[#​3687](AzureAD/microsoft-identity-web#3687).
- Add validation baseline exclusions. See
[#​3684](AzureAD/microsoft-identity-web#3684).
- Add dSTS integration tests. See
[#​3677](AzureAD/microsoft-identity-web#3677).
- Fix FIC test. See
[#​3663](AzureAD/microsoft-identity-web#3663).
- Update IdentityWeb version, build logic, and validation. See
[#​3659](AzureAD/microsoft-identity-web#3659).

### New Contributors
* @​XiaoxinMS2 made their first contribution in
AzureAD/microsoft-identity-web#3677
* @​RyAuld made their first contribution in
AzureAD/microsoft-identity-web#3687
* @​agocke made their first contribution in
AzureAD/microsoft-identity-web#3664
* @​MZOLN made their first contribution in
AzureAD/microsoft-identity-web#3700
* @​christian-posta made their first contribution in
AzureAD/microsoft-identity-web#3644
* @​4gust made their first contribution in
AzureAD/microsoft-identity-web#3682
* @​rayluo made their first contribution in
AzureAD/microsoft-identity-web#3714

Commits viewable in [compare
view](AzureAD/microsoft-identity-web@4.3.0...4.4.0).
</details>

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score](https://dependabot-badges.githubapp.com/badges/compatibility_score?dependency-name=Microsoft.Identity.Web&package-manager=nuget&previous-version=4.3.0&new-version=4.4.0)](https://docs.github.com/en/github/managing-security-vulnerabilities/about-dependabot-security-updates#about-compatibility-scores)

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Signed-off-by: dependabot[bot] <support@github.com>
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This was referenced Mar 3, 2026
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