flake: Test_TaskSend/WaitsForWorkingAppState

[flake-investigator]

CI Run Link: https://github.com/coder/coder/actions/runs/26021908346
Failing Job: https://github.com/coder/coder/actions/runs/26021908346/job/76485426908 (test-go-pg (windows-2022))

Commit Info:

• SHA: 6a79f5f62ed189256788c0ce217b7ccb93a73398
• Author: Ethan
• Commit title: fix: ignore drifting timestamp in stories (#25429)

Failure Evidence:

clitest.go:299: command "coder task send" exited with error: running command "coder task send": wait for task "bad-raynor1461/test-task" to be idle:
    github.com/coder/coder/v2/cli.(*RootCmd).taskSend.func1
        C:/actions-runner/coder/coder/cli/task_send.go:111
  - context deadline exceeded
...
Test:       Test_TaskSend/WaitsForWorkingAppState
--- FAIL: Test_TaskSend/WaitsForWorkingAppState (26.14s)

Notes:

• Failure is Windows-only in this run (linux/macOS test-go-pg jobs passed).
• No panic/OOM or data race output detected in the logs.

Root Cause Classification:
A. Flaky Test (timeout waiting for task/app to become idle)

Precise Assignment Analysis:

• Failing test located in cli/task_send_test.go subtest WaitsForWorkingAppState (around lines 271-309).
• git log --oneline -10 --follow cli/task_send_test.go shows the most relevant recent change: 4bcd2b90 (Mathias Fredriksson) "test(cli): fix context timeout in task tests".
• This change directly relates to timeout handling in task tests; assigning to @mafredri for triage.

Related Issues:

• None found after searching for "Test_TaskSend", "WaitsForWorkingAppState", "task_send_test.go", and "wait for task" in coder/internal.

Reproduction:

• go test ./cli -run 'Test_TaskSend/WaitsForWorkingAppState' -count=50 (especially on Windows runners)