flake: TestActiveServer_AnthropicProviderToolPreRequestGuard #1589

CI Failure Details

CI Run: https://github.com/coder/coder/actions/runs/27441018780
Failed Job: https://github.com/coder/coder/actions/runs/27441018780/job/81114905916 (test-go-pg-17)
Commit: d6aa3d61ee4ad38b60d887641ff8084f4b676c2b (TJ) coder/coder@d6aa3d6

Failing Test

TestActiveServer_AnthropicProviderToolPreRequestGuard/allowed_web_search_survives_when_provider_tool_is_enabled

File: coderd/x/chatd/chatd_test.go (around line ~6957)

Error Output

=== FAIL: coderd/x/chatd TestActiveServer_AnthropicProviderToolPreRequestGuard/allowed_web_search_survives_when_provider_tool_is_enabled (31.12s)
    chatd_test.go:6957:
        Error Trace: /home/runner/work/coder/coder/testutil/eventually.go:45
                     /home/runner/work/coder/coder/coderd/x/chatd/chatd_chainmode_test.go:493
                     /home/runner/work/coder/coder/coderd/x/chatd/chatd_test.go:6957
        Error:       Received unexpected error:
                     context deadline exceeded
        Messages:    Eventually timed out
    chatd_test.go:6960:
        Error:       "[...]" should have 2 item(s), but has 1

Error Analysis

The test waits for a second Anthropic streaming request after inserting a provider tool pair message and sending a follow-up user message. The testutil.Eventually loop timed out (context deadline exceeded), and the recorded requests list only contained 1 item instead of the expected 2.

Root Cause Assessment

Likely flaky timing in chatd processing or request recording for provider tool guard scenarios; the second generation request was not observed before the test deadline.

Data Race / Panic / OOM Checks

Searched the job logs for WARNING: DATA RACE, panic:, out of memory, signal: killed — none found.

Assignment Analysis

Intended blame command:

• git blame -L 6930,6985 coderd/x/chatd/chatd_test.go

Proxy via history (available tooling):

• git log --oneline -10 --follow coderd/x/chatd/chatd_test.go
  • Most recent substantive change touching this test file: 4debd23c ("fix: chatd refactor") by Hugo Dutka.

Assigning to @hugodutka as the most recent modifier of the failing test area.

Related Issues

Searched coder/internal for:

• TestActiveServer_AnthropicProviderToolPreRequestGuard
• AnthropicProviderToolPreRequestGuard
• coderd/x/chatd/chatd_test.go
• context deadline exceeded + chatd

No matching issues found.

Reproduction

go test ./coderd/x/chatd -run TestActiveServer_AnthropicProviderToolPreRequestGuard/allowed_web_search_survives_when_provider_tool_is_enabled -count=1