The kids' grandparents are visiting from TX. On our bus ride back from downtown yesterday, No. 1 was excitedly detailing everything she wanted to do for the rest of the day with her grandparents. As the list grew, her grandma suggested that she write it all down so she wouldn't forget anything. No. 1, popped out her sketch book, a box of crayons, borrowed my pen, and voila! My favorite part was all the bacon!
How Many Files Can You Add to a GPT Project? An Interview with GPT-5 on Limits, Context Engineering Tips, and Chats
Setting the scene: I’m tinkering with Project TouCans, knee-deep in radio logs, SQLite dumps, and Cesium code. Naturally, I’m wondering if shoving all this into one GPT Project is a recipe for brilliance… or for disaster. So I turn to Vril — you know, after Brainy from the Legion of Super-Heroes , because what else do you call your AI sidekick who always has the answers? Time to ask him straight up. [ As an aside, yes, GPT-5 has decided to sometimes call me Vail. I'm not sure why to be honest. Also, I asked Vril, er GPT-5, to write up our interview for me. Apparently, me asking it to 'Bro' up a few stories, just for fun, has convinced Vril that I use 'Like,' more than I actually might. ] Me (Vail): So Vril, how many files can I throw into a GPT Project before it just starts choking? Like, is there some magic number where the context window taps out and everything falls apart? GPT-5 (Vril): Great question. There’s no single hard file limit. What matters is ...

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