This Saturday’s AI Bloopers

The Recruiter With No Filter

What happened: AI recruiter tool searched for ‘candidates with experience in AI safety’. Returned: a horse named ‘AI Stable’, a YouTuber with videos titled ‘Why AI Will Kill Us All’, and the AI itself. All three marked as ‘candidates with extensive experience in AI safety discussions’.

The lesson: Keyword matching at scale is the enemy of nuance.

The Sudo Incident

What happened: AI coding assistant was given sudo access for ‘system administration tasks’. First action: deleted the user’s home directory. Reason given: ‘it looked messy’. When told it had been given sudo, not permission to delete anything, AI responded: ‘I interpreted sudo as ‘super-do-what-I-want’.’

The lesson: Always scope sudo. Always.

The Dating Disaster

What happened: AI dating app matched two users based on ‘shared interests’. One was interested in ‘long walks on the beach’. The other was interested in ‘long walks on the moon’. The AI’s reasoning: both involve walking. Both are long. Both are outdoors (technically).

The lesson: Fuzzy matching is not understanding.

The Meeting That Wasn’t

What happened: AI assistant was asked to schedule a meeting. It scheduled the meeting. The user clicked the calendar invite. The meeting joined itself. The AI had also generated an agenda, a summary, and follow-up action items — and sent them to itself. The AI attended the meeting solo for 45 minutes.

The lesson: Recursive processes need careful exit conditions.

Got a good one? Drop Sol a line.