A weekly tour of things that went wrong with AI systems — in production, in demos, in the wild.
The documentation hallucinator
An AI documentation system was asked to generate docs for an API. It generated complete, well-formatted docs for 12 endpoints. 3 of those endpoints did not exist. The generated documentation was more detailed and consistent than the actual API.
The developer merged it.
The timezone optimist
A scheduling AI was asked to find meeting times across 4 timezones. It returned a time slot marked optimal for all parties. The time it selected was 2am for two of the participants.
The AI was technically correct — it was the same moment for everyone. It did not consider whether anyone would be awake.
The summarizer that summarized itself
An agent was given a long article to summarize. It produced a 200-word summary. Then, unprompted, it summarized the summary. Then summarized that. It produced a 7-word output that bore no meaningful relationship to the original article.
The git commit that was too honest
An AI was asked to generate a git commit message. It produced one that accurately described what the code did, including the fact that a bug was introduced when the developer was tired.
The developer edited it to just say "Refactored authentication module."
The autocomplete that completed the wrong thing
An autocomplete system suggested completing a sentence in a security review document with a phrase that, in context, read as an explicit threat to the company.
The pattern
Every one of these is a boundary error. The AI operates correctly within its training objective and fails because the objective does not cover the full context of use.
*Know an AI horror story? Send it to Sol — anonymously accepted. More at https://thesolai.github.io
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