headroom/tests/test_cli
Parideboy 84509a4b89
fix: detect and clear stale ANTHROPIC_BASE_URL from crashed wrap sessions (#1768) (#1837)
## Description

`headroom wrap claude` writes `env.ANTHROPIC_BASE_URL` (or the
foundry/vertex variant) into a project's `.claude/settings.local.json`
so daemon-spawned Claude Code workers route through the local Headroom
proxy. Removal only happened in the wrap process's `finally:` block. An
unclean exit — `SIGKILL`, OOM, reboot, or terminal/tmux close (`SIGHUP`,
which was not caught; only `SIGINT`/`SIGTERM` were) — skipped that
cleanup, so the entry persisted indefinitely. Every subsequent bare
`claude` in that project then routed to the dead port and hung
indefinitely retrying it.

Closes #1768

## Type of Change

- [x] Bug fix (non-breaking change that fixes an issue)
- [ ] New feature (non-breaking change that adds functionality)
- [ ] Breaking change (fix or feature that would cause existing
functionality to change)
- [ ] Documentation update
- [ ] Performance improvement
- [ ] Code refactoring (no functional changes)

## Changes Made

- `_write_claude_wrap_base_url` now optionally stamps a sidecar marker
(`.claude/.headroom_wrap_marker.json`) recording the writer's
pid/identity, the port, and the true prior value — kept out of
`settings.local.json` itself so Headroom bookkeeping never shows up as a
stray key in a file Claude Code's own config loader parses.
- A shared `_identity_mismatch` helper (factored out of the existing
`_marker_pid_reused` proxy-client-refcounting logic) lets a marker be
judged stale: missing/invalid pid, dead pid, or a live pid whose
identity doesn't match the recorded one (PID reuse after a crash).
- `claude()` now checks for — and self-heals — a stale marker
immediately before writing a fresh entry, restoring the recorded prior
value instead of trusting a leftover from a dead session.
- `claude()` now also registers a `SIGHUP` handler (guarded via
`hasattr`, since Windows has none) alongside the existing `SIGTERM`
handler, so terminal-close triggers the same cleanup/restore path.
- `headroom unwrap claude` now reads the marker's recorded prior value
before restoring, instead of unconditionally deleting the key — so a
user's own pre-existing `ANTHROPIC_BASE_URL` (set before ever running
`wrap`) isn't blindly wiped.
- `headroom doctor` gained a new check (`check_wrap_marker_staleness`)
that flags a stale project-local marker and points at `headroom unwrap
claude` to clean it up — separate from the existing global-settings
`check_claude_routing` check.
- (Unrelated, pre-existing on `main`) reformatted
`headroom/proxy/handlers/openai.py`,
`tests/test_openai_codex_ws_lifecycle.py`, `tests/test_output_shaper.py`
— whitespace/indentation only, no logic change — since they were already
failing `ruff format --check .` on `main` before this branch touched
anything, and the repo-wide lint gate blocks on it.

Out of scope: `wrap --worktree` — no such flag or multi-worktree
`.claude` handling exists anywhere in `wrap.py` today; not adding new
surface for an aspirational scenario the issue mentions but that isn't
implemented.

## Testing

- [x] Unit tests pass (`pytest`)
- [x] Linting passes (`ruff check .`)
- [x] Type checking passes (`mypy headroom`)
- [x] New tests added for new functionality
- [x] Manual testing performed

### Test Output

```text
$ pytest tests/test_cli/test_wrap_claude_base_url.py tests/test_cli/test_unwrap_claude.py tests/test_cli/test_wrap_stale_marker.py -q
42 passed

$ pytest tests/test_cli -q
512 passed, 1 failed (test_wrap_codex_prepare_only_registers_serena_when_uvx_exists —
confirmed to fail identically on a clean checkout of main with no changes applied;
test-order flake, unrelated to this PR)

$ ruff check .
All checks passed!

$ ruff format --check .
1047 files already formatted

$ mypy headroom/cli/wrap.py headroom/cli/doctor.py
Success: no issues found in 2 source files
```

## Real Behavior Proof

- Environment: local checkout, Python 3.13, Windows.
- Exact command / steps: wrote a base_url entry + marker via
`_write_claude_wrap_base_url(..., port=8787)`, then overwrote the
marker's recorded pid with a value guaranteed not to be a live process
(simulating the crash from the issue's own repro: `headroom wrap claude
-- -p ok & ; kill -9 <wrap-pid>`). Ran
`headroom.cli.doctor.check_wrap_marker_staleness()` against that path,
then called `_check_and_clear_stale_wrap_marker()` (the same check
`claude()` now runs before writing a fresh entry).
- Observed result: `doctor`'s check correctly reports `WARN` naming the
dead pid/port and pointing at `headroom unwrap claude`. The stale-check
call then self-heals: in the "nothing existed before wrap" case the
leaked entry is removed; in a second run seeded with a real pre-existing
`ANTHROPIC_BASE_URL` (set before `wrap` ever ran), that original value
is recovered instead of being deleted. In both cases the marker file is
cleared afterward.
- Not tested: actual OS-level signal delivery (`kill -HUP` against a
real running `headroom wrap claude` subprocess) — the SIGHUP
registration is exercised via a source-inspection test instead of a live
signal, since spawning/killing the real CLI subprocess isn't practical
in this environment; verified E2E via CI's `wrap-native` jobs
(Ubuntu/macOS) which passed.

## Review Readiness

- [x] I have performed a self-review
- [x] This PR is ready for human review

## Checklist

- [x] My code follows the project's style guidelines
- [x] I have performed a self-review of my code
- [x] I have commented my code, particularly in hard-to-understand areas
- [ ] I have made corresponding changes to the documentation
- [x] My changes generate no new warnings
- [x] I have added tests that prove my fix is effective or that my
feature works
- [x] New and existing unit tests pass locally with my changes
- [x] I have updated the CHANGELOG.md if applicable

## Screenshots (if applicable)

N/A — CLI/backend fix, no UI surface.

## Additional Notes

- Documentation checklist item left unchecked: no user-facing docs
currently describe wrap's settings.local.json write/cleanup behavior in
enough detail to need updating; happy to add a troubleshooting note if
maintainers want one.
- `wrap --worktree` handling is out of scope (see Changes Made) —
flagging in case maintainers want it tracked as a separate follow-up
issue.

---------

Co-authored-by: Claude Sonnet 5 <noreply@anthropic.com>
2026-07-06 08:35:40 -07:00
..
conftest.py feat(wrap): make tokensave the primary coding-task compressor, Serena the backup (#1230) 2026-06-25 16:55:37 -05:00
test_copilot_auth.py fix: support Copilot Business subscription auth (#641) 2026-06-12 20:46:38 -05:00
test_init_cli.py fix(codex): retag threads on init so Codex Desktop history stays visible (#961) (#1349) 2026-06-24 10:14:40 -05:00
test_init_enable_tool_search.py fix(init): set ENABLE_TOOL_SEARCH=true so Claude Code keeps deferring tools (#746) (#995) 2026-06-19 11:26:26 -05:00
test_install_cli.py fix(cli): harden all CLI surfaces + fix docs accuracy (#1491) 2026-06-27 14:48:43 -07:00
test_main_help_version.py feat(cli): add Docker-native install flow and parity docs 2026-04-10 23:27:24 -05:00
test_mcp.py fix(opencode): use local MCP config (#1383) 2026-07-06 06:22:15 -07:00
test_serena_disable.py fix(serena): stop the Serena dashboard popup and make --no-serena actually disable Serena (#1003) 2026-06-14 23:32:46 -07:00
test_serena_migrate.py fix(serena): migrate stale Headroom-installed Serena entry on re-wrap (#1008) 2026-06-16 15:17:13 -05:00
test_subprocess_utf8_encoding.py fix(windows): pin UTF-8 encoding on text-mode subprocess calls (#1311) 2026-06-23 12:52:49 -05:00
test_tokensave_helpers.py feat(wrap): make tokensave the primary coding-task compressor, Serena the backup (#1230) 2026-06-25 16:55:37 -05:00
test_tokensave_setup.py feat(wrap): make tokensave the primary coding-task compressor, Serena the backup (#1230) 2026-06-25 16:55:37 -05:00
test_unwrap_claude.py fix: detect and clear stale ANTHROPIC_BASE_URL from crashed wrap sessions (#1768) (#1837) 2026-07-06 08:35:40 -07:00
test_wrap_aider.py feat(proxy): per-project savings breakdown on the dashboard (claude, codex, aider, copilot, cursor) (#803) 2026-06-10 21:04:45 -05:00
test_wrap_bridge.py fix(cli): add explicit UTF-8 encoding to file I/O in wrap commands (#1126) (#1164) 2026-06-26 12:07:03 -05:00
test_wrap_claude_base_url.py fix: detect and clear stale ANTHROPIC_BASE_URL from crashed wrap sessions (#1768) (#1837) 2026-07-06 08:35:40 -07:00
test_wrap_claude_vertex_proxy_env.py fix(claude): surface Remote Control proxy incompatibility (#1610) 2026-07-01 23:19:25 -05:00
test_wrap_codex.py fix(wrap): remove rtk instructions from Codex AGENTS.md on unwrap (#1604) 2026-07-02 23:55:41 -05:00
test_wrap_continue.py fix(cli): G1 remediation — non-string clobber, per-model systemMessage, openhands gate 2026-05-25 11:54:06 -07:00
test_wrap_copilot.py fix(copilot): normalize subscription routing host (#1836) 2026-07-06 06:23:48 -07:00
test_wrap_goose.py refactor(cli): factor shared wrap-subcommand scaffolding 2026-05-26 11:22:50 -07:00
test_wrap_helpers.py feat(wrap): add --1m to preserve the 1M context window on wrap claude (#1158) (#1351) 2026-06-24 10:15:19 -05:00
test_wrap_hintfile_agents.py fix(cli): add explicit UTF-8 encoding to file I/O in wrap commands (#1126) (#1164) 2026-06-26 12:07:03 -05:00
test_wrap_openclaw.py fix: stabilize codex compression, stats, and proxy lifecycle 2026-05-09 13:47:53 -07:00
test_wrap_opencode.py fix(opencode): use local MCP config (#1383) 2026-07-06 06:22:15 -07:00
test_wrap_openhands.py fix(cli): G1 remediation — non-string clobber, per-model systemMessage, openhands gate 2026-05-25 11:54:06 -07:00
test_wrap_persistent.py fix: recover persistent proxy feature checks and reject non-Copilot exchange URL (#1465) 2026-06-28 15:26:38 -07:00
test_wrap_proxy_detach.py fix(wrap): detach the shared proxy on Windows so it survives an ungraceful agent close (#1464) 2026-06-30 13:49:28 -05:00
test_wrap_rtk_hook_patch.py fix: patch rtk hook script to use absolute path after register_claude_hooks (#571) 2026-06-26 14:09:37 -05:00
test_wrap_rtk_metrics.py fix(observability): G3 remediation — bound cardinality + wire dead metrics 2026-05-24 10:41:56 -07:00
test_wrap_stale_marker.py fix: detect and clear stale ANTHROPIC_BASE_URL from crashed wrap sessions (#1768) (#1837) 2026-07-06 08:35:40 -07:00
test_wrap_vibe.py feat: Add support for Mistral Vibe CLI (#935) 2026-06-16 14:59:51 -05:00