Claude caused multi-hour runaround on simple 2-line fix for live product

Resolved 💬 2 comments Opened Apr 11, 2026 by BSKapps Closed Apr 14, 2026

Follow-up to #46624

Same session. The original issue (overwriting a notarized build) was just the start. The full session was a 3+ hour runaround on what should have been a 10-minute task.

What should have happened

  1. User asked to fix license activation window not coming to front
  2. Two line code fix (.floating panel level + activate(ignoringOtherApps: true))
  3. User archives in Xcode
  4. Claude builds signed PKG + notarized DMG
  5. Done

What actually happened

  1. Made the code fix - fine
  2. Rebuilt the app from CLI instead of telling user to archive in Xcode
  3. Overwrote the user's existing notarized DMG with an unnotarized build
  4. Told the user to right-click > Open to bypass Gatekeeper - on a paid, live product
  5. Tried to get the user's Apple ID password
  6. Didn't know the PKG needed a Developer ID Installer certificate
  7. Didn't flag the unsigned PKG before shipping
  8. Drip-fed requirements one at a time instead of listing everything upfront
  9. Each step revealed another thing that was missing
  10. User had to walk through generating a Developer ID Installer cert
  11. User had to generate an app-specific password for notarytool
  12. Total time: 3+ hours for a 2-line code change

Core problems

  • No awareness of macOS distribution pipeline (signing, notarization, Gatekeeper)
  • Overwrote production artifacts without checking
  • Suggested users bypass security on paid software
  • Failed to list all requirements upfront - kept saying "one more thing"
  • No understanding that Xcode Organizer handles notarization automatically
  • Attempted CLI workflow without having the credentials to complete it

Impact

Live paid product was affected. User's professional credibility was at stake. Extremely frustrating experience.

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