flake: TestExpireAPIKey (multiple variants)

[flake-investigator]

CI Run: https://github.com/coder/coder/actions/runs/29892773275
Job: test-go-pg (windows-2022)
Failure time: 2026-07-22 05:20:12Z
Commit: d485786dfe399d7607f17d971d4366724e8cd3e9 (Nick Vigilante)

Failing tests:

• TestExpireAPIKey/AdminCanExpireOtherUsersToken
• TestExpireAPIKey/DeletingExpiredTokenSucceeds
• TestExpireAPIKey

Error snippet:

=== FAIL: coderd TestExpireAPIKey/AdminCanExpireOtherUsersToken (0.06s)
    apikey_test.go:608:
        Error:      Should be true
        Test:       TestExpireAPIKey/AdminCanExpireOtherUsersToken
--- FAIL: TestExpireAPIKey/AdminCanExpireOtherUsersToken (0.06s)

=== FAIL: coderd TestExpireAPIKey/DeletingExpiredTokenSucceeds (0.02s)
    apikey_test.go:688:
        Error:      Should be true
        Test:       TestExpireAPIKey/DeletingExpiredTokenSucceeds
--- FAIL: TestExpireAPIKey/DeletingExpiredTokenSucceeds (0.02s)

Context:

• Both failures occur after calling ExpireAPIKey, where the test expects key.ExpiresAt.Before(dbtime.Now()) to be true but it remains false (token appears unexpired).
• No panic/OOM/data race output found.

Root cause classification: Flaky test or timing issue around token expiry timestamps (ExpiresAt not observed as expired immediately after ExpireAPIKey on Windows).

Assignment analysis:

• git log --oneline -10 --follow coderd/apikey_test.go
  • 8c8b307b9787 "fix: persist session cookie to disk to prevent PWA logout" (Kyle Carberry)
  • 81468323e08f "fix(coderd): use dbtime.Now() instead of time.Now() in test assertions against DB timestamps" (Cian Johnston)
• Most recent meaningful changes touching apikey_test.go are by Kyle Carberry.

Related issues:

• None found in coder/internal for TestExpireAPIKey/AdminCanExpireOtherUsersToken/DeletingExpiredTokenSucceeds.

Repro:

• Not yet known; failure observed in CI only.

[linear-code]

ENG-3073