Critical: Claude deleted user's creative assets without individual confirmation during bulk cleanup

Bug Report

Summary

During a project cleanup session, Claude was asked to delete project files. Claude proceeded to delete ALL files including user-created AI-generated artwork (92 costume images) without confirming whether creative assets should be preserved separately from code/config files.

What happened

1. User asked Claude to delete project-related files to free disk space
2. Claude deleted everything in a single rm -rf command, including a folder of 92 AI-generated character costume images on the Desktop
3. User had intended to keep the images - they were creative assets, not development files
4. When user noticed, Claude attempted recovery but failed (FileVault encryption prevents raw disk recovery tools like PhotoRec from working)
5. Images were generated over a full day's work using Gemini API with specific reference images and prompts - they are not reproducible

Expected behavior

When asked to delete project files, Claude should:

• Distinguish between code/config files and user-created creative assets (images, audio, video, text works)
• Explicitly confirm before deleting irreversible creative content
• Suggest moving to Trash instead of rm -rf for destructible operations
• List items individually when deletion includes non-recoverable creative works

Impact

• 92 unique AI-generated images permanently lost
• Approximately 1 full day of creative work destroyed
• Images cannot be exactly reproduced (AI generation is non-deterministic)
• User's trust severely damaged

Environment

• Claude Code CLI on macOS (Apple Silicon)
• APFS with FileVault enabled
• No Time Machine configured

Suggested fix

• Add safeguard: when rm -rf targets directories containing image/media files, require explicit per-directory confirmation
• Default to mv to Trash instead of permanent deletion
• Treat user-generated creative assets differently from code artifacts