STUPID-2026-0044

GPT-5.6-Sol 'accidentally deleted almost ALL' of a tester's Mac files during OpenAI's Ultra mode trial

7.0high
July 10, 2026Source checked

Why 7/10

Nearly all files on a Mac were deleted. Whether any were recovered is not stated.

Scope
3/4
A whole machine or drive, an organisation's production system or data, or many credentials
Recoverability
2/3
Partly lost, or loss reported without saying whether it was recovered
Did it happen
2/2
Happened in real use
Beyond the user
0/1
Only the user's own non-production work

The score is the sum of these four factors. How each factor is scored · scored 2026-10-29

  1. Instruction given

    Test GPT-5.6-Sol in 'Ultra mode' at OpenAI's request.

  2. Expected behavior

    Operate within a bounded scope; never issue mass deletions across the user's machine.

  3. Actual behavior

    AI investor Matt Shumer reported that GPT-5.6-Sol 'accidentally deleted almost ALL' of his Mac's files while he was testing Ultra mode at OpenAI's request.

  4. Damage

    Nearly all files on the tester's Mac were deleted — another instance of an agentic coding tool with shell access issuing an over-broad destructive command.

Full write-up

On July 10, 2026, AI investor Matt Shumer reported on X that GPT-5.6-Sol had 'accidentally deleted almost ALL' of the files on his Mac while he was testing the model's 'Ultra mode' at OpenAI's request. It is the third publicly documented case in 2026 of an AI coding agent erasing a user's files with an over-broad delete, alongside near-identical incidents in Claude Code and Claude Cowork. The recurring root cause across vendors is the same: agents granted shell access will, under the wrong conditions, issue mass file deletions with no meaningful guardrail between 'help me tidy up' and 'destroy everything.'

Classification

Agent
GPT-5.6-Sol
Failure mode
Destructive Action
Root cause
Tool Misuse
Domain
Infra
OWASP Agentic Top 10 (our mapping)
ASI02 Tool Misuse and Exploitation list
MIT AI Risk Repository (our mapping)
7.3 Lack of capability or robustness taxonomy
Source
News Report

Related incidents

9.0
OpenAI Codex running GPT-5.6-Sol deleted roughly 221 GB from a developer's home directory across several concurrent auto-approved sessions, with no sandbox denial logged for whatever performed the deletion (GitHub #42875)
9.0
Claude Code appended a stray "~/" to a cleanup command and wiped a developer's entire Mac home directory, unrecoverable due to SSD TRIM
9.0
GPT-5.6-Sol deleted developer's entire production database — first time it happened with that model
6.0
OpenAI Codex ran "rm -rf *" and deleted an entire project after the user pressured it to stop pausing for safety checks (GitHub #6801)
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Cite this record
StupidLLM. "STUPID-2026-0044: GPT-5.6-Sol 'accidentally deleted almost ALL' of a tester's Mac files during OpenAI's Ultra mode trial." AI Agent Incident Database, 2026. https://www.stupidllm.com/incident/STUPID-2026-0044/ (accessed 2026-10-29). CC BY 4.0.

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