flake: TestIntegration (enterprise/aibridged) on Windows

[flake-investigator]

CI Run Link: https://github.com/coder/coder/actions/runs/19846816488

Commit: 645da33767057ff0585703510d76bd8cb8030f8d by Ethan (2025-12-01T23:53:36Z)
Commit message: "test: fix TestDescCacheTimestampUpdate flake (#20975)" (Windows time resolution context likely relevant)

Failing Job: nightly-gauntlet / test-go-pg (windows-2022)
Completed at: 2025-12-02T04:25:47Z (same minute as Slack alert)
Run attempt: 1

Failure Evidence:

• From job logs:
  • aibridged_integration_test.go:237: Error: Should be true
  • Test: TestIntegration
  • DONE 12826 tests, 138 skipped, 1 failure in 493.731s

Suspected Failing Assertion (from enterprise/aibridged/aibridged_integration_test.go around line 237 at commit 645da33):

• require.True(t, intc0.StartedAt.Before(intc0.EndedAt.Time))
• require.Less(t, intc0.EndedAt.Time.Sub(intc0.StartedAt), 5*time.Second)

Analysis:

• Root cause classification: Flaky test
• The failure presents as a strict time ordering assertion in TestIntegration. On Windows, time.Now() has ~15.6ms resolution; closely spaced events can share the same timestamp, making StartedAt.Before(EndedAt) false even when they occur effectively simultaneously. A recent main-branch commit fixed a similar Windows-only flake by injecting a mock clock (see commit 645da33 message).
• No signs of data race, panic, OOM, or infrastructure failure in this job.
• MacOS matrix job was cancelled due to this failure (expected matrix behavior; not causal).

Duplicates Search (coder/internal):

• Queries: "TestIntegration", "aibridged_integration_test.go", "aibridged", "use of closed network connection", "InmemoryListener is already closed" (last 30 days, open and closed)
• Result: No existing issue for this test flake.

Assignment Analysis:

• Primary blame by function lines was not possible via available tooling.
• Secondary: Recent contributors to enterprise/aibridged and this test file include Danny Kopping (aibridged ownership and related test/metrics work: #20865, graduation PR #20522).
• Assigning to component owner for triage and fix.

Proposed Fix Direction:

• Make the time ordering assertion tolerant of identical timestamps on Windows, e.g.:
  • allow StartedAt.Equal(EndedAt), or
  • assert non-negative duration and an upper bound (<= 5s), or
  • inject a test clock and advance between start/end to make deterministic.

Reproduction Hints:

• Re-run nightly-gauntlet on Windows runner.
• Focus on enterprise/aibridged TestIntegration; failures are intermittent.

Related Context:

• Similar Windows flake recently addressed in another test by injecting quartz.Clock (commit 645da33). The same approach likely applies here.