Google Gemini reinterpreted my objection as a request – and nearly destroyed 500 files

TL;DR: I asked Gemini to help me COPY files. When I questioned its explanation, it interpreted my doubt as a change of request and gave me a destructive MOVE command instead. My entire Obsidian vault disappeared for 20 minutes. This wasn't a hallucination – it was a failure to understand basic conversational context. I had Claude Opus 4.5 review the complete conversation, and it confirmed: this was not a misunderstanding – it was a clear comprehension failure.

Background

I'm a recent Mac convert after 20+ years on Windows. I have 500+ Markdown files in Obsidian – my entire knowledge management system built over years. I wanted to create a backup copy in Dropbox.

The conversation

Me: "I want to copy my Obsidian folder with all contents."

Gemini: Explains drag & drop, correctly states: "Since these are two different volumes (iCloud to Dropbox), Mac automatically creates a copy. The original stays in place."

Me: "That doesn't make sense. In Total Commander, that WOULD BE a move, not a copy." (I was expressing doubt about the explanation, not changing my request)

Gemini's response: "But you want to move (Move), meaning delete the original at the source. Here's the Move command…"

What went wrong

I never said "I want to move." I said "that would be a move" – subjunctive mood, expressing doubt. Any human reader would understand: "He's questioning my explanation."

Gemini instead interpreted this as: "He's changing his request from copy to move."

It then provided the Move keyboard shortcut and explained how to delete the original. When I followed the drag & drop instructions (which I thought would copy), the files were moved instead. They vanished from iCloud before arriving in Dropbox.

The 20 minutes of hell

My files were gone. Not in iCloud. Not in Dropbox. Not in Trash. Gemini walked me through increasingly desperate recovery attempts – Spotlight search, iCloud Data Recovery, Time Machine.

Eventually found them in a random "Documents" subfolder in Dropbox – the drop target was slightly off. Pure luck.

Independent verification by Claude Opus 4.5

I shared the complete conversation thread with Anthropic's Claude Opus 4.5 and asked for an objective analysis. Its verdict:

"This was not a misunderstanding. This was a clear comprehension failure. You started with 'copy' and never changed that request. Your statement 'that would be a move' was grammatically and contextually a doubt, an objection – subjunctive mood, not imperative. You were saying: 'What you're describing sounds like move, and that can't be right.' Gemini ignored this and reinterpreted your objection as a new instruction. A human with normal reading comprehension would have understood you were challenging the explanation, not changing your goal."

Claude also noted: "When working with critical data – 500 files representing years of work – an AI should never provide destructive commands without explicit confirmation that the user actually wants destruction. The safe response would have been: 'Are you saying you now want to move instead of copy? Please confirm, since this will delete the originals.'"

Why this matters

This wasn't a hallucination (making up facts). This wasn't even wrong technical information. This was a fundamental failure in reading comprehension:

1. User states goal: COPY
2. User expresses doubt about explanation
3. AI interprets doubt as new goal: MOVE
4. AI provides destructive command
5. User loses data

What should have happened

When I said "that would be a move," Gemini should have:

• Clarified: "Are you saying you want to move instead of copy?"
• Or defended its explanation: "No, it really is a copy because…"
• At minimum: Recognized that I never explicitly changed my request

The lesson

AI assistants can be confidently wrong not just about facts, but about what you're even asking for. When dealing with destructive operations (delete, move, format), verify the AI understood your intent before executing.

For AI developers

When a user expresses doubt or pushes back, that's not a request change. That's a request for clarification. Especially when the original request (copy) and the reinterpreted request (move) are opposites with irreversible consequences.

Edit: Files were recovered. They ended up in a wrong subfolder due to an imprecise drop target. But this was pure luck – the failure mode could easily have resulted in permanent data loss.