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
- User asked to fix license activation window not coming to front
- Two line code fix (
.floatingpanel level +activate(ignoringOtherApps: true)) - User archives in Xcode
- Claude builds signed PKG + notarized DMG
- Done
What actually happened
- Made the code fix - fine
- Rebuilt the app from CLI instead of telling user to archive in Xcode
- Overwrote the user's existing notarized DMG with an unnotarized build
- Told the user to right-click > Open to bypass Gatekeeper - on a paid, live product
- Tried to get the user's Apple ID password
- Didn't know the PKG needed a Developer ID Installer certificate
- Didn't flag the unsigned PKG before shipping
- Drip-fed requirements one at a time instead of listing everything upfront
- Each step revealed another thing that was missing
- User had to walk through generating a Developer ID Installer cert
- User had to generate an app-specific password for notarytool
- 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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