[CI] Expired Apple development certificates break signing-dependent PR tests

[dalexsoto]

Summary

The Apple development certificates installed in the PR-test signing keychains expired on July 31, 2026. Signing-dependent tests now fail with:

No valid iOS/tvOS/macOS code signing keys found in keychain.

• Stable signature: expired-apple-development-certificates-no-valid-code-signing-keys
• Classification: CI infrastructure failure
• Distinct monitored PRs: 4
• Confirmed job occurrences: 17
• First confirmed by the monitor: 2026-07-31T14:42:07Z
• Latest confirmed occurrence: 2026-07-31T16:30:04Z

Affected PRs

• [tests] Skip event add/remove accessors in the documentation cecil-test #26297, head 7e56322bf7c853b1c4ef12626f02cccf36d26fe5
  • Build 14833205, attempt 1
  • Failed jobs: dotnettests_ios, dotnettests_tvos, dotnettests_macos, monotouch_ios, monotouch_tvos, msbuild, and Windows Dotnet tests
• [SecurityInterface] Update bindings up to Xcode 27.0 Beta 4 #26281, head 2df8ff4002b2b5a6d461eeb47a45b9bf576130df
  • Build 14834283, attempt 1
  • Failed job: msbuild
• [net11.0] Update dependencies from dotnet/macios #26380, head 85c0366c6c1b1233983943d0d59f08633b291c3c
  • Build 14834129, attempt 1
  • Failed jobs: dotnettests_tvos, dotnettests_macos, monotouch_ios, monotouch_tvos, and msbuild
• [release/11.0.1xx-preview7] Update dependencies from dotnet/macios #26381, head bf31c1874c3da70065394e2cf9a8feadbf722c34
  • Build 14834130, attempt 1
  • Failed jobs: dotnettests_tvos, monotouch_ios, monotouch_tvos, and msbuild

Diagnostic evidence

• DetectSigningIdentityTaskTests fails because no valid iOS signing key remains.
• Detailed MSBuild test reports confirm that the installed Apple development certificates are expired.
• iOS, tvOS, and macOS app-build tests then fail in signing detection; the later test-suite summaries are consequences of that same root cause.
• The first failed task in each listed job is Run tests. No publication or missing-artifact failure is classified separately.

Reproduction pattern and impact

Any PR test job that builds a signing-dependent device or extension configuration after the certificate expiry can fail. The issue currently blocks four monitored PRs and affects simulator, Windows-remote, MSBuild, and app-build test jobs across iOS, tvOS, and macOS.

Investigation performed

The Azure timelines, TestSummary reports, detailed NUnit reports, and representative binlogs were inspected. Searches across open and closed dotnet/macios issues used the exact error, DetectSigningIdentityTaskTests, keychain-signing terms, and expired-certificate terms. Issues #7171 and #20671 contain the same user-facing error but describe unrelated project/configuration problems, not expired CI credentials.

Retry status

• [tests] Skip event add/remove accessors in the documentation cecil-test #26297: no retry submitted. The durable budget is 3 lifetime retries and 0 for the current head.
• [SecurityInterface] Update bindings up to Xcode 27.0 Beta 4 #26281, [net11.0] Update dependencies from dotnet/macios #26380, and [release/11.0.1xx-preview7] Update dependencies from dotnet/macios #26381: no retry submitted; their initial builds are still active.
• Retrying before replacement credentials are validated would deterministically repeat the failure.

Resolution / workaround

Renew and replace the Apple development certificates and associated provisioning profiles in the secure CI signing bundle/keychains. Validate the replacement with a full signing-dependent simulator run. After validation, rerun failed jobs; if Windows Integration is affected, rerun its entire stage.

Azure artifacts and detailed reports are retention-limited.

[dalexsoto]

New evidence for expired-apple-development-certificates-no-valid-code-signing-keys:

• Classification: CI infrastructure failure
• Distinct monitored PRs: 4
• Confirmed job occurrences: 24 total, 7 new
• [SecurityInterface] Update bindings up to Xcode 27.0 Beta 4 #26281, head 2df8ff4002b2b5a6d461eeb47a45b9bf576130df, build 14834283 attempt 1:
  • dotnettests_tvos
  • monotouch_ios
  • monotouch_tvos
• [net11.0] Update dependencies from dotnet/macios #26380, head 85c0366c6c1b1233983943d0d59f08633b291c3c, build 14834129 attempt 1:
  • dotnettests_ios
  • Windows Dotnet tests
• [release/11.0.1xx-preview7] Update dependencies from dotnet/macios #26381, head bf31c1874c3da70065394e2cf9a8feadbf722c34, build 14834130 attempt 1:
  • dotnettests_ios
  • Windows Dotnet tests

Both Windows reports contain 14 failed remote tests, and all 14 report no valid iOS signing key. The diagnosis remains expired Apple development certificates in the CI signing keychain.

No retries were submitted: these initial builds remain active and replacement credentials are not validated. #26297 remains at 3 lifetime retries and 0 for its current head. The workaround remains renewing the secure signing bundle, validating it with a full signing-dependent run, then rerunning failed jobs (or the entire Windows Integration stage where applicable).

Issue-specific checklist: none present. Helix evidence: not applicable.

[dalexsoto]

Four additional occurrences for expired-apple-development-certificates-no-valid-code-signing-keys:

• Classification: CI infrastructure failure
• Distinct monitored PRs: 4
• Confirmed job occurrences: 28 total, 4 new
• [SecurityInterface] Update bindings up to Xcode 27.0 Beta 4 #26281, head 2df8ff4002b2b5a6d461eeb47a45b9bf576130df, build 14834283 attempt 1:
  • dotnettests_macos: the failed macOS test reports no valid macOS signing key.
  • Windows Dotnet tests: all 10 failed remote tests report no valid iOS signing key.
  • dotnettests_ios: 64 failed iOS test cases report no valid iOS signing key.
• [release/11.0.1xx-preview7] Update dependencies from dotnet/macios #26381, head bf31c1874c3da70065394e2cf9a8feadbf722c34, build 14834130 attempt 1:
  • dotnettests_macos: the failed macOS test reports no valid macOS signing key.

#26381 merged at 2026-07-31T16:58:04Z and has left the monitoring union; its initial simulator build was still active at the latest refresh.

No retries were submitted. The initial #26281/#26380 builds remain active, credentials remain expired, and no replacement signing bundle has been validated. Diagnosis and workaround are unchanged.

Issue-specific checklist: none present. Helix evidence: not applicable.

[dalexsoto]

Retry status update for expired-apple-development-certificates-no-valid-code-signing-keys:

• [SecurityInterface] Update bindings up to Xcode 27.0 Beta 4 #26281, head 2df8ff4002b2b5a6d461eeb47a45b9bf576130df
• Original failed simulator run: 14834283
• New manual full-pipeline run: 14835738
• Trigger: manual, dalexsoto
• Accepted: 2026-07-31T18:10:19Z
• Current state: in progress; package and Linux builds are running
• Retry budget after reconciliation: 4 lifetime / 1 current head

Retained Azure timelines account for three older-head retry waves plus this new run. Automatic downstream Publish Test Results attempts were not counted separately.

There are no new failure occurrences in this update; the canonical count remains 28 occurrences across 4 PRs. Run 14835738 will serve as the validation for replacement signing credentials. Diagnosis and workaround remain unchanged until its signing-dependent jobs complete.

Issue-specific checklist: none present. Helix evidence: not applicable.

[dalexsoto]

Retry validation failure for expired-apple-development-certificates-no-valid-code-signing-keys:

• [SecurityInterface] Update bindings up to Xcode 27.0 Beta 4 #26281, head 2df8ff4002b2b5a6d461eeb47a45b9bf576130df
• Manual retry run: 14835738, attempt 1
• Failed job: msbuild
• Failed task: Run tests (log 1790)
• Completed: 2026-07-31T18:41:08Z
• Signature: No valid iOS code signing keys found in keychain

The replacement signing credentials are not valid: DetectSigningIdentityTaskTests reproduced the same certificate failure. This is occurrence 29 across 4 monitored PRs.

Run 14835738 remains active, so no equivalent retry may be submitted. Retry accounting remains 4 lifetime / 1 current head. Diagnosis and workaround are unchanged.

Issue-specific checklist: none present. Helix evidence: not applicable.

[dalexsoto]

Three more failures in #26281 retry run 14835738, head 2df8ff4002b2b5a6d461eeb47a45b9bf576130df:

• monotouch_tvos: all 19 signing-dependent configurations are BuildFailure.
• monotouch_ios: all 19 signing-dependent configurations are BuildFailure.
• dotnettests_tvos: device-build tests reproduce the invalid signing-key failure.

The canonical count is now 32 occurrences across 4 PRs. Run 14835738 remains active and retry accounting remains 4 lifetime / 1 current head.

No further retry is permitted while the equivalent run is active. The validation continues to show that signing credentials are still invalid; diagnosis and workaround are unchanged.

Issue-specific checklist: none present. Helix evidence: not applicable.

[dalexsoto]

Three additional failures in #26281 retry run 14835738, head 2df8ff4002b2b5a6d461eeb47a45b9bf576130df:

• Windows Dotnet tests: 10 remote iOS device-build tests failed with the signing-key pattern.
• dotnettests_ios: 64 iOS device-build test failures match the invalid signing-key signature.
• dotnettests_macos: the macOS extension build reproduces the invalid macOS signing-key failure.

The canonical count is now 35 occurrences across 4 PRs. Run 14835738 remains active, with retry accounting unchanged at 4 lifetime / 1 current head.

No further retry is permitted while this equivalent run is active. The validation continues to confirm that signing credentials remain invalid; diagnosis and workaround are unchanged.

Issue-specific checklist: none present. Helix evidence: not applicable.

[dalexsoto]

Final outcome for #26281 retry run 14835738, head 2df8ff4002b2b5a6d461eeb47a45b9bf576130df:

• Completed: 2026-07-31T20:10:10Z
• Result: failed
• Successful jobs: 30
• Failed jobs: 7
• All failed jobs reproduce the expired-certificate signing signature already recorded in this issue.
• No new occurrence identities were added; the canonical count remains 35 across 4 PRs.
• Retry accounting remains 4 lifetime / 1 current head.

This validation confirms the signing credentials were not replaced successfully. No further retry is authorized until a renewed signing bundle is independently validated; rerunning unchanged credentials would deterministically repeat the failure.

Issue-specific checklist: none present. Helix evidence: not applicable.

[dalexsoto]

New affected PR for expired-apple-development-certificates-no-valid-code-signing-keys:

• [release/11.0.1xx-preview7] Update dependencies from dotnet/dotnet #26384, head d45f335fdc825b4e849a5f8e0ef783531448949e
• Initial simulator run: 14840799, attempt 1
• msbuild: DetectSigningIdentityTaskTests reports no valid iOS signing key.
• monotouch_ios: all 23 signing-dependent configurations are BuildFailure.
• monotouch_tvos: all 23 signing-dependent configurations are BuildFailure.

The canonical count is now 38 occurrences across 5 monitored PRs. Build 14840799 remains active, so no retry was submitted. The diagnosis and workaround remain unchanged.

Issue-specific checklist: none present. Helix evidence: not applicable.

[dalexsoto]

One additional occurrence on #26384, head d45f335fdc825b4e849a5f8e0ef783531448949e:

• Build 14840799, attempt 1
• dotnettests_tvos
• Run tests log 2469
• Completed: 2026-08-01T02:48:24Z
• The tvOS device-build tests reproduce the invalid signing-key pattern.

The canonical count is now 39 occurrences across 5 monitored PRs. Build 14840799 remains active, so no retry was submitted. Diagnosis and workaround are unchanged.

Issue-specific checklist: none present. Helix evidence: not applicable.

[dalexsoto]

Two additional occurrences on #26384, head d45f335fdc825b4e849a5f8e0ef783531448949e, build 14840799, attempt 1:

• dotnettests_ios: iOS device-build tests reproduce the invalid signing-key signature.
• dotnettests_macos: the macOS extension build reproduces the invalid macOS signing-key signature.

The canonical count is now 41 occurrences across 5 monitored PRs. Build 14840799 remains active, so no retry was submitted. Diagnosis and workaround are unchanged.

Issue-specific checklist: none present. Helix evidence: not applicable.

[dalexsoto]

One additional occurrence and one identity correction for expired-apple-development-certificates-no-valid-code-signing-keys:

• Correction: the three prior [release/11.0.1xx-preview7] Update dependencies from dotnet/dotnet #26384 updates used an invalid full head-SHA suffix. Azure build 14840799 triggerInfo.pr.sourceSha and GitHub both confirm the head is d45f335fdc821987a0d0086ebd976c6efb545806. The PR, run, jobs, and existing occurrence count are unchanged.
• [release/11.0.1xx-preview7] Update dependencies from dotnet/dotnet #26384, corrected head d45f335fdc821987a0d0086ebd976c6efb545806, build 14840799, attempt 1
• Windows Dotnet tests: 14 of 34 remote iOS device-build tests failed; every failure reports No valid iOS code signing keys found in keychain.
• Evidence: Run .NET tests remotely log 2797 and Fail if test failures log 2800; job completed 2026-08-01T03:30:22Z.

The canonical count is now 42 occurrences across 5 monitored PRs. Build 14840799 completed failed at 2026-08-01T03:47:30Z.

No retry was submitted. Replacement signing credentials remain unvalidated, and the failed Windows Integration stage must be rerun as an entire stage. The separate macOS checkout failure in this run is tracked in #26385.

Issue-specific checklist: none present. Helix evidence: not applicable.

[dalexsoto]

Retry outcome for expired-apple-development-certificates-no-valid-code-signing-keys:

• PR [tests] Skip event add/remove accessors in the documentation cecil-test #26297 at 7e56322bf7c853b1c4ef12626f02cccf36d26fe5: Azure run 14833205, attempt 2 was an external failed-jobs retry (actor unavailable) and completed failed. Accounting is 4 lifetime retries / 1 on this head.
• The canonical expired-certificate count remains 42 confirmed occurrences across 5 PRs. This attempt failed before certificate validation: six Simulator tests jobs (f74aa053, 9a2ea658, 30656afa, a82441db, 3da4f9e8, c300ddf5) failed in List secure files because macios-certificates-and-provisioning-profiles.zip is absent. This is 6 occurrences of the new missing-bundle signature on 1 PR.
• Windows Dotnet tests job 9e1d9d57 failed independently because it reused a macOS reservation assigned to build 14850072. Reserve macOS bot for tests remained at attempt 1, so the external action did not rerun the full Windows stage.
• Classification: CI infrastructure failure. The signing bundle is currently absent, so replacement credentials are still not usable. No further retry is permitted until a renewed bundle is independently validated; any future Windows retry must rerun the entire stage.
• Additional info to collect: none.