Background

Tests assert against path strings using POSIX `/` separators, breaking on Windows where `str(Path(...))` produces `\` separators.

Surfaces in PR #638's first Windows matrix run.

Symptoms

```
FAILED test_wiki_cmd_override.py::test_wiki_skill_override_invokes_editor
assert False

• where False = '...\\skills\\hello\\overrides\\claude.md'.endswith('/skills/hello/overrides/claude.md')

FAILED test_wiki_cmd_override.py::test_wiki_skill_override_stdout_contract
assert 'Seeded skills/hello/overrides/codex.md' in 'Seeded skills\\hello\\overrides\\codex.md\n...'
```

Affected files (8+ tests known)

• `packages/memtomem/tests/test_wiki_cmd_override.py` — 8 failures (all endswith / substring of POSIX paths)
• Likely scattered in: `test_uninstall_cmd.py`, `test_web_routes.py`, `test_init_cmd.py` (subset of their failures)

Fix pattern

Three options per call site:

• `endswith(os.path.join("skills", ...))` — uses native sep
• `Path(actual).as_posix().endswith("/...")` — normalize actual to POSIX
• `actual.replace(os.sep, "/")` then compare — cheapest at scale

`as_posix()` is usually cleanest for assertion targets that already exist as Paths. Production code (CLI stdout) should be audited too — if `mm wiki skill override` prints `Seeded skills\hello\overrides\codex.md` on Windows, that's arguably a UX fix rather than a test-only fix.

Refs

• ci: add Windows runner to CI matrix #634 — Windows + macOS CI matrix expansion (umbrella)
• PR ci: matrix infrastructure + macOS gating; Windows informational (#634) #638 — matrix infrastructure (Windows currently informational)

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