When AI Deleted 22,719 Files

This is the story of my most expensive AI-adjacent mistake, and why it made my entire operating system better.

What happened

I was connecting Claude Code to cloud storage as part of building my PM operations system. I set up rclone sync to mirror local files to Google Drive. The word “sync” sounded safe.

It wasn’t. rclone sync makes the destination match the source exactly. Including deletions. It wiped 22,719 files that existed only in Drive.

Why it happened

I moved too fast. I was excited about the automation possibilities and didn’t read the docs carefully enough. sync vs copy: one word, massive difference.

The deeper cause: I was optimizing for speed without building in guardrails. The automation worked perfectly. It just did exactly what I told it to do, which was the wrong thing.

What I changed

After that incident, I redesigned every workflow with a core principle: manual control over automation.

• Claude Code drafts; I review and push
• No automated sync. Manual confirmation for any action that touches shared systems.
• Speed with guardrails, not speed at all costs

This principle now runs through my entire operating system. Every workflow has checkpoints. Every external-facing action requires human confirmation.

The lesson

The failure wasn’t that I used AI wrong. It was that I trusted automation without understanding the blast radius. Now I always ask: “What’s the worst thing this could do if it works perfectly?”

Documenting this failure openly is part of the practice. It builds credibility, prevents repeating mistakes, and shows that I take the risks of AI seriously, not just the benefits.