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Fix macOS Tailscale CLI discovery for App Store installs#35

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Ninja3047 merged 2 commits intomainfrom
fix-macos-tailscale
Feb 16, 2026
Merged

Fix macOS Tailscale CLI discovery for App Store installs#35
Ninja3047 merged 2 commits intomainfrom
fix-macos-tailscale

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Summary

  • On macOS, Tailscale installed via the App Store places its CLI at /Applications/Tailscale.app/Contents/MacOS/Tailscale, which is not in PATH
  • check_local_tailscale() was running ["tailscale", ...] which fails with FileNotFoundError, incorrectly reporting Tailscale as unavailable
  • Added find_tailscale_cli() helper that checks PATH first, then falls back to the macOS App Store location on darwin

Test plan

  • New TestFindTailscaleCli tests cover: PATH hit, macOS App Store fallback, app not installed, Linux (no fallback), PATH skips fallback
  • Updated TestCheckLocalTailscale tests to use find_tailscale_cli mock
  • Added race-condition safety net test (test_tailscale_binary_vanishes)
  • Full test suite passes (274 tests)
  • prek run passes

🤖 Generated with Claude Code

On macOS, Tailscale installed via the App Store places its CLI at
/Applications/Tailscale.app/Contents/MacOS/Tailscale, which is not in
PATH. Add find_tailscale_cli() helper that checks PATH first, then
falls back to the macOS App Store location on darwin.

Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>
@Ninja3047 Ninja3047 requested a review from ret2libc as a code owner February 14, 2026 20:49
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@DarkaMaul DarkaMaul left a comment

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Sounds great, two nitpicks:

  • maybe the tests are a bit too comprehensive here (I flagged the binary_vanishes)
  • the missing binary error is not surfaced to the user - we could maybe have a better error message here

Distinguish "Tailscale not found" from "not running" when the local
check fails, so users know whether to install or start Tailscale.
Remove the overly comprehensive binary_vanishes race condition test.

Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>
@Ninja3047 Ninja3047 merged commit b5c0998 into main Feb 16, 2026
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@Ninja3047 Ninja3047 deleted the fix-macos-tailscale branch February 16, 2026 17:48
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3 participants