When A Custom GPT's Instructions Work Great Until Someone Uploads A File
This story is from 2026-09-21. It is preserved in the archive; the latest stories are on the live feed.
A custom GPT built with a carefully scoped system prompt often behaves exactly as intended, right up until a user uploads a document mid conversation and asks the bot to work with it. At that point, a whole category of instructions that governed the bot's behavior perfectly well in pure conversatio…
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- 2026-09-21 05:42 · DEV Community — AI
When A Custom GPT's Instructions Work Great Until Someone Uploads A File