Error messages explained
The exact message you hit, what causes it, and how to get past it.
11 guides
The 3 causes of "something went wrong while analyzing your file"
The analysis step failed, not the upload, so file size is not the cause. 3 things explain almost every case. Retry once, test a 2 line file, then check yours.
ChatGPT says your file is too large. Which of the 4 caps did you hit?
4 caps produce this message: 512 MB per file, 50 MB spreadsheets, 20 MB images, 2M tokens of text. Under 10 MB means length, and compressing will not help.
Why ChatGPT says "you can send up to -1 files"
A negative count is a display fault, not a real limit: your allowance minus whatever is already counted. 5 things push it under zero, and the fixes in order.
"You may only upload 1 file at a time" in ChatGPT
20 files per message is the web cap since February 2026, so this is a per message block, not your account or your quota. Send 1 per message, or bundle them.
"You have reached our limit of file uploads": the 2 causes
2 documented causes: failed uploads count toward the 80 per 3 hours cap, and 25 GB of storage never clears on its own. Deleting chats no longer frees it.
Why ChatGPT says your conversation is too long
The chat is full, not the file. Messages, replies and uploaded files share one total, so the same file uploads fine in a new chat. How to move across cleanly.
ChatGPT cannot read your scanned PDF
Every plan except Enterprise extracts digital text and discards images, and a scan is all image. A 2 second test to confirm it, then the OCR route that works.
ChatGPT file upload not working? Find your error here
Hit the limit having uploaded 1 file? Failed attempts count toward the 80 per 3 hours cap. Every ChatGPT upload error here, with the fix that clears it.
ChatGPT file upload stuck loading? The 4 causes, and the 1 minute test
An upload that spins forever has 4 common causes. A 1 line text file in incognito tells you which one, in under a minute. Stop retrying: failed attempts count.
Why ChatGPT forgets a file you already uploaded
Nothing deleted the file. The chat outgrew its context window, so the oldest content stopped being sent. Re-attach it, and the setup that stops it recurring.
ChatGPT will not accept that file type. Convert it, do not rename it.
ChatGPT rejects the format before anything uploads, so renaming the extension never helps. Convert to PDF, DOCX, TXT or CSV, and tell 3 refusals apart.