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headroom/tests/test_cli_update.py
Rod Boev 2678bb1db6
fix(update): let Windows self-update replace headroom.exe (#2016) 
## Description

`headroom update` currently runs pip from the same `headroom.exe`
process pip needs to replace. On Windows that leaves the launcher locked
and the upgrade fails mid-uninstall. This reroutes Windows pip-based
self-update through a short delayed Python helper that replays the
original pip argv after the current launcher exits. Other update paths
stay synchronous, and the printed upgrade command stays exact for manual
recovery.

Closes #1941

## 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

- Replace the Windows-only `cmd.exe /c` handoff for `pip` and `pip-user`
self-update with a short Python helper that replays the original pip
argv after the launcher exits.
- Keep every pip value, including extras, as argv data through the
delayed child and preserve the manual recovery output.
- Keep pipx, uv-tool, and non-Windows behavior unchanged.
- Add focused regression coverage for extras containing `&`, `|`, and
`>`.

## Testing

- [x] Unit tests pass
- [x] Linting passes
- [ ] Type checking passes
- [x] New tests added for new functionality when applicable
- [ ] Manual testing performed

### Test Output

```text
uv run pytest tests/test_cli_update.py tests/test_update_helpers.py -q
66 passed

uv run ruff check headroom/cli/update.py tests/test_cli_update.py tests/test_update_helpers.py
All checks passed

uv run ruff format --check headroom/cli/update.py tests/test_cli_update.py tests/test_update_helpers.py
3 files already formatted
```

## Real Behavior Proof

- Environment: Windows pip install
- Exact command / steps: run `headroom update --extras "foo&calc"`,
accept the prompt, and wait for the child pip output
- Observed result: Windows pip and pip-user updates now launch the
original pip command through a short delayed Python helper argv, so
extras stay one argument end to end, while pipx and non-Windows paths
remain synchronous in the focused test coverage
- Not tested: live Windows run on this host
- Scope: Windows pip self-update

## 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
- [ ] 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
- [ ] I have updated the CHANGELOG.md if applicable

## Additional Notes

The printed upgrade command stays unchanged so the manual recovery path
remains exact and copy-pasteable.

---------

Co-authored-by: JerrettDavis <mxjerrett@gmail.com>
2026-07-14 11:52:47 -04:00

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"""Tests for the `headroom update` command + install-method detection."""
from __future__ import annotations
import sys
import pytest
from click.testing import CliRunner
from headroom.cli import update as up
from headroom.cli.main import main
@pytest.fixture(autouse=True)
def _clean_env(tmp_path, monkeypatch):
monkeypatch.setenv("HEADROOM_WORKSPACE_DIR", str(tmp_path))
monkeypatch.delenv("PIPX_HOME", raising=False)
monkeypatch.delenv("UV_TOOL_DIR", raising=False)
monkeypatch.delenv("CONDA_PREFIX", raising=False)
# Default: not a checkout / editable / docker / managed install.
monkeypatch.setattr(up, "_is_source_checkout", lambda: False)
monkeypatch.setattr(up, "_is_editable_install", lambda: False)
monkeypatch.setattr(up, "_in_docker", lambda: False)
monkeypatch.setattr(up, "_is_externally_managed", lambda: False)
# --------------------------------------------------------------------------- #
# detect_install_method
# --------------------------------------------------------------------------- #
def test_detect_checkout(monkeypatch):
monkeypatch.setattr(up, "_is_source_checkout", lambda: True)
m = up.detect_install_method()
assert m.kind == "checkout" and m.can_self_update is False and "git pull" in m.guidance
def test_detect_editable(monkeypatch):
monkeypatch.setattr(up, "_is_editable_install", lambda: True)
m = up.detect_install_method()
assert m.kind == "editable" and m.can_self_update is False
def test_detect_docker(monkeypatch):
monkeypatch.setattr(up, "_in_docker", lambda: True)
m = up.detect_install_method()
assert m.kind == "docker" and m.can_self_update is False
def test_detect_pipx_by_path(monkeypatch):
monkeypatch.setattr(up.sys, "prefix", "/home/u/.local/pipx/venvs/headroom-ai")
m = up.detect_install_method()
assert m.kind == "pipx" and m.argv == ["pipx", "upgrade", "headroom-ai"]
def test_detect_pipx_windows_path(monkeypatch):
monkeypatch.setattr(up.sys, "prefix", r"C:\\Users\\u\\pipx\\venvs\\headroom-ai")
m = up.detect_install_method()
assert m.kind == "pipx"
def test_detect_uv_tool(monkeypatch):
monkeypatch.setattr(up.sys, "prefix", "/home/u/.local/share/uv/tools/headroom-ai")
m = up.detect_install_method()
assert m.kind == "uv-tool" and m.argv == ["uv", "tool", "upgrade", "headroom-ai"]
def test_detect_venv_uses_current_interpreter(monkeypatch):
monkeypatch.setattr(up, "_in_virtualenv", lambda: True)
m = up.detect_install_method()
assert m.kind == "pip"
assert m.argv[:4] == [sys.executable, "-m", "pip", "install"]
assert "-U" in m.argv and "headroom-ai" in m.argv
def test_detect_venv_with_extras(monkeypatch):
monkeypatch.setattr(up, "_in_virtualenv", lambda: True)
m = up.detect_install_method(extras="all")
assert "headroom-ai[all]" in m.argv
def test_detect_user_site(monkeypatch):
monkeypatch.setattr(up, "_in_virtualenv", lambda: False)
monkeypatch.setattr(up, "_package_location", lambda: "/home/u/.local/site")
monkeypatch.setattr(up, "_is_user_site_install", lambda loc: True)
m = up.detect_install_method()
assert m.kind == "pip-user" and "--user" in m.argv
def test_detect_externally_managed_refuses(monkeypatch):
monkeypatch.setattr(up, "_in_virtualenv", lambda: False)
monkeypatch.setattr(up, "_is_user_site_install", lambda loc: False)
monkeypatch.setattr(up, "_is_externally_managed", lambda: True)
m = up.detect_install_method()
assert m.kind == "system" and m.can_self_update is False
assert "PEP 668" in m.guidance
# --------------------------------------------------------------------------- #
# `headroom update` command
# --------------------------------------------------------------------------- #
def test_update_already_current(monkeypatch):
monkeypatch.setattr(up, "installed_version", lambda: "0.26.0")
monkeypatch.setattr(up, "fetch_latest_version", lambda **k: "0.26.0")
res = CliRunner().invoke(main, ["update"])
assert res.exit_code == 0
assert "up to date" in res.output
def test_update_check_reports_command_without_running(monkeypatch):
monkeypatch.setattr(up, "installed_version", lambda: "0.26.0")
monkeypatch.setattr(up, "fetch_latest_version", lambda **k: "0.27.0")
monkeypatch.setattr(up, "_in_virtualenv", lambda: True)
def _no_run(*a, **k):
raise AssertionError("subprocess.run must not be called with --check")
monkeypatch.setattr(up.subprocess, "run", _no_run)
res = CliRunner().invoke(main, ["update", "--check"])
assert res.exit_code == 0
assert "Update available: 0.26.0 → 0.27.0" in res.output
assert "pip" in res.output and "install" in res.output
def test_update_runs_upgrade_with_yes(monkeypatch):
calls = {}
monkeypatch.setattr(up, "installed_version", lambda: "0.26.0")
monkeypatch.setattr(up, "fetch_latest_version", lambda **k: "0.27.0")
monkeypatch.setattr(up, "_in_virtualenv", lambda: True)
monkeypatch.setattr(up.sys, "platform", "linux")
monkeypatch.setattr(up, "_find_core_pyd", lambda: None) # Skip integrity checks
class _Result:
returncode = 0
def _run(argv, *a, **k):
calls["argv"] = argv
return _Result()
monkeypatch.setattr(up.subprocess, "run", _run)
res = CliRunner().invoke(main, ["update", "--yes"])
assert res.exit_code == 0
assert calls["argv"][:4] == [sys.executable, "-m", "pip", "install"]
assert "upgraded to 0.27.0" in res.output
def test_update_windows_pip_handoff_uses_popen(monkeypatch):
calls = {}
monkeypatch.setattr(up, "installed_version", lambda: "0.26.0")
monkeypatch.setattr(up, "fetch_latest_version", lambda **k: "0.27.0")
monkeypatch.setattr(up.sys, "platform", "win32")
def _detect(extras=None):
calls["extras"] = extras
return up.InstallMethod(
kind="pip",
can_self_update=True,
argv=[
r"C:\Python313\python.exe",
"-m",
"pip",
"install",
"-U",
"headroom-ai[foo&calc]",
],
)
monkeypatch.setattr(up, "detect_install_method", _detect)
def _run(*a, **k):
raise AssertionError("Windows pip handoff must not call subprocess.run")
def _popen(argv, *a, **k):
calls["argv"] = argv
return object()
monkeypatch.setattr(up.subprocess, "run", _run)
monkeypatch.setattr(up.subprocess, "Popen", _popen)
res = CliRunner().invoke(main, ["update", "--yes", "--extras", "foo&calc"])
assert res.exit_code == 0
assert calls["extras"] == "foo&calc"
assert calls["argv"][:2] == [sys.executable, "-c"]
assert "subprocess.run" in calls["argv"][2]
assert calls["argv"][3:] == [
"-m",
"pip",
"install",
"-U",
"headroom-ai[foo&calc]",
]
assert "headroom.exe" in res.output
def test_update_windows_non_pip_path_stays_synchronous(monkeypatch):
calls = {}
monkeypatch.setattr(up, "installed_version", lambda: "0.26.0")
monkeypatch.setattr(up, "fetch_latest_version", lambda **k: "0.27.0")
monkeypatch.setattr(up.sys, "platform", "win32")
monkeypatch.setattr(
up,
"detect_install_method",
lambda extras=None: up.InstallMethod(
kind="pipx",
can_self_update=True,
argv=["pipx", "upgrade", "headroom-ai"],
),
)
def _popen(*a, **k):
raise AssertionError("pipx must stay on the synchronous path")
monkeypatch.setattr(up, "safe_update", lambda argv: calls.setdefault("safe_update", argv) and 0)
monkeypatch.setattr(up.subprocess, "Popen", _popen)
res = CliRunner().invoke(main, ["update", "--yes"])
assert res.exit_code == 0
assert calls["safe_update"] == ["pipx", "upgrade", "headroom-ai"]
def test_update_refuses_in_checkout(monkeypatch):
monkeypatch.setattr(up, "installed_version", lambda: "0.26.0")
monkeypatch.setattr(up, "fetch_latest_version", lambda **k: "0.27.0")
monkeypatch.setattr(up, "_is_source_checkout", lambda: True)
def _no_run(*a, **k):
raise AssertionError("must not upgrade a checkout")
monkeypatch.setattr(up.subprocess, "run", _no_run)
res = CliRunner().invoke(main, ["update", "--yes"])
assert res.exit_code == 0
assert "git pull" in res.output
def test_update_network_failure(monkeypatch):
monkeypatch.setattr(up, "installed_version", lambda: "0.26.0")
monkeypatch.setattr(up, "fetch_latest_version", lambda **k: None)
res = CliRunner().invoke(main, ["update"])
assert res.exit_code != 0
assert "Could not reach PyPI" in res.output
def test_update_upgrade_failure_surfaces_command(monkeypatch):
monkeypatch.setattr(up, "installed_version", lambda: "0.26.0")
monkeypatch.setattr(up, "fetch_latest_version", lambda **k: "0.27.0")
monkeypatch.setattr(up, "_in_virtualenv", lambda: True)
monkeypatch.setattr(up.sys, "platform", "linux")
monkeypatch.setattr(up, "_find_core_pyd", lambda: None) # Skip file operations in test
class _Result:
returncode = 1
monkeypatch.setattr(up.subprocess, "run", lambda *a, **k: _Result())
res = CliRunner().invoke(main, ["update", "--yes"])
assert res.exit_code != 0
assert "Upgrade failed" in res.output
# --------------------------------------------------------------------------- #
# safe_update (Windows-specific backup/restore protection)
# --------------------------------------------------------------------------- #
def test_safe_update_success(monkeypatch):
"""Test safe_update returns 0 when the command succeeds."""
class _Result:
returncode = 0
monkeypatch.setattr(up, "_find_core_pyd", lambda: None)
monkeypatch.setattr(up.subprocess, "run", lambda *a, **k: _Result())
result = up.safe_update([sys.executable, "-m", "pip", "install", "-U", "headroom-ai"])
assert result == 0
def test_safe_update_handles_missing_pyd(monkeypatch):
"""Test safe_update when _core.pyd doesn't exist."""
class _Result:
returncode = 0
monkeypatch.setattr(up, "_find_core_pyd", lambda: None)
monkeypatch.setattr(up.subprocess, "run", lambda *a, **k: _Result())
result = up.safe_update([sys.executable, "-m", "pip", "install", "-U", "headroom-ai"])
assert result == 0
def test_safe_update_passes_through_failure(monkeypatch):
"""Test safe_update returns error code when pip fails."""
class _Result:
returncode = 1
monkeypatch.setattr(up, "_find_core_pyd", lambda: None)
monkeypatch.setattr(up.subprocess, "run", lambda *a, **k: _Result())
result = up.safe_update([sys.executable, "-m", "pip", "install", "-U", "headroom-ai"])
assert result == 1
def test_safe_update_warns_but_no_backup_when_locked(monkeypatch, tmp_path):
"""When the .pyd is locked, safe_update warns but does not make a backup."""
fake_pyd = tmp_path / "_core.pyd"
fake_pyd.write_bytes(b"fake pyd content")
monkeypatch.setattr(up.sys, "platform", "win32")
monkeypatch.setattr(up, "_find_core_pyd", lambda: fake_pyd)
monkeypatch.setattr(up, "_is_pyd_locked", lambda p: True) # locked!
class _Result:
returncode = 1 # pip fails (expected — file was locked)
monkeypatch.setattr(up.subprocess, "run", lambda *a, **k: _Result())
result = up.safe_update([sys.executable, "-m", "pip", "install", "-U", "headroom-ai"])
assert result == 1
# Backup should never be created — file is locked, pip fails without corruption
assert not (tmp_path / "_core.pyd.bak").exists()
def test_safe_update_backup_and_restore_on_integrity_failure(monkeypatch, tmp_path):
"""Test safe_update backs up and restores _core.pyd if integrity check fails."""
# Create a fake .pyd file
fake_pyd = tmp_path / "_core.pyd"
fake_pyd.write_bytes(b"fake pyd content")
# Mock Windows and _core.pyd detection
monkeypatch.setattr(up.sys, "platform", "win32")
monkeypatch.setattr(up, "_find_core_pyd", lambda: fake_pyd)
monkeypatch.setattr(up, "_is_pyd_locked", lambda p: False)
class _Result:
returncode = 0
# Simulate pip success but integrity test failure
monkeypatch.setattr(up.subprocess, "run", lambda *a, **k: _Result())
monkeypatch.setattr(up, "_test_core_integrity", lambda: False)
result = up.safe_update([sys.executable, "-m", "pip", "install", "-U", "headroom-ai"])
# Should return error due to integrity failure
assert result == 1
# Backup should be cleaned up
assert not (tmp_path / "_core.pyd.bak").exists()
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