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Added retry counter for acquire token and modified added a test with …#3682

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bgavrilMS merged 2 commits intomasterfrom
4gust/infinite-retry-fix
Feb 9, 2026
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Added retry counter for acquire token and modified added a test with …#3682
bgavrilMS merged 2 commits intomasterfrom
4gust/infinite-retry-fix

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@4gust 4gust commented Jan 27, 2026

Fix Certificate Reload Infinite Recursion Bug
Description
Certificate reload logic was triggering for all invalid_client errors, not just certificate-related ones. This caused unnecessary retries for unrelated authentication failures like wrong passwords or missing app registrations.
Additionally, the shared _retryClientCertificate boolean flag had thread-safety issues in concurrent scenarios.
Solution
Restored specific error checking - Only reload certificates for actual cert errors:
• AADSTS700027 - Invalid key
• AADSTS700024 - Invalid time range
• AADSTS7000214 - Certificate revoked
• AADSTS1000502 - Certificate expired Replaced shared flag with per-call counter - Each call tracks its own retry count (max 1 retry),
preventing infinite loops and other conditions.
Fixes issues :
#3654

Changes
• Added MaxCertificateRetries = 1 constant
• Updated IsInvalidClientCertificateOrSignedAssertionError(MsalServiceException) to accept retryCount parameter
• Retry logic now distinguishes between legitimate cert errors (can retry) vs config errors (no retry)
• Added retry counter tracking through token acquisition call stack

@4gust 4gust requested a review from a team as a code owner January 27, 2026 15:05
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This looks good. Another option would be to use the extensibility API https://github.com/AzureAD/microsoft-authentication-library-for-dotnet/blob/main/src/client/Microsoft.Identity.Client/Extensibility/ConfidentialClientApplicationBuilderExtensions.cs#L123. This way you would just have to configure the retry in the callback. Add it to the CCA builder. @bgavrilMS thoughts? I think that would be a cleaner approach.

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Approving if you would like to go with this approach.

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bgavrilMS commented Feb 9, 2026

This looks good. Another option would be to use the extensibility API https://github.com/AzureAD/microsoft-authentication-library-for-dotnet/blob/main/src/client/Microsoft.Identity.Client/Extensibility/ConfidentialClientApplicationBuilderExtensions.cs#L123. This way you would just have to configure the retry in the callback. Add it to the CCA builder. @bgavrilMS thoughts? I think that would be a cleaner approach.

But in this case, the entire TokenAcquirer needs to be reset, so as to force a certificate re-load:

image

I don't think this can be done with OnMsalFailure, because you can't get a CCA instance which was created with WithCertificate to reload the cert. We'd have to move to use WithCertificate(() => x509) which is a lot of work.

@bgavrilMS bgavrilMS merged commit 0f0f93e into master Feb 9, 2026
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@bgavrilMS bgavrilMS deleted the 4gust/infinite-retry-fix branch February 9, 2026 18:09
This was referenced Mar 1, 2026
github-actions bot pushed a commit to EelcoLos/nx-tinkering that referenced this pull request Mar 3, 2026
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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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This was referenced Mar 3, 2026
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