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PDF uploads failing to complete

I have attached to documents to a chat. the icons show the upload completed (tick marks) but when I hover over the send button to initate the AI query request it states that the upload is not complete. First time I tried it did not show this and then simply hung for a long time after which the model stated there was no upload.

I’m using chatGPT 5.5 with 2 websearch

Status: Completed18 comments

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Comments18

  • Violet Cake

  • Mark Florkowski

    Team

    It seems like a recent change we made to improve token estimation broke PDF uploads for some users. We have released a fix for what we believe to be the root cause now, let us know if you still encounter any issues

    • Purple Pickletop

      I can upload them now but an error pops up

      • Mark Florkowski

        Team

        Taking a look!

        • Mark Florkowski

          Team

          Can you try starting a new chat or branching from before you first tried to attach the file? It seems like there might be some bad state stuck in the chat from the initial failures.

          • Purple Pickletop

            how can I branch it from before the errors? I’d need to have everything in the same chat

            • Purple Pickletop

              It works tho, now I can upload them pdfs to other chats so it’s fixed, only thing left to do is what should I do with my chat, I guess that just start all over again sending the previos pdfs and messages I sent

            • Mark Florkowski

              Team

              Click this button on one of the messages before the failed attachment attempts. You can then continue the conversation in the new branched chat, with all the previous history

              • Purple Pickletop

                I did branch as u told me and the new branch did error anyways

                • Purple Pickletop

                  I did also branch from another previous message that wasnt a pdf upload just in case, same error

                  • Mark Florkowski

                    Team

                    hm are there other pdfs earlier in the conversation?

                    • Purple Pickletop

                      yes, but they did work properly when I uploaded them

                      Should I just try to start the chat from 0?

                      • Mark Florkowski

                        Team

                        I think you may need to. It seems the issue is actually with one of the earlier PDFs.

                        • Mark Florkowski

                          Team

                          Will continue looking on our side as well

                          • Purple Pickletop

                            Everything works fine in the new chat so fine by me!

                            btw, what can I do when this comes out?

                            Branching would help?

                            • Purple Pickletop

                              That’s my last pdf I swear, I will just need to upload a couple pics of my projetc tomorrow? Will it work? Wil it be super slow?

                              • Mark Florkowski

                                Team

                                That message is letting you know that you have used most of your available chat limits. You should still be able to use it, but keep in mind that long chats with lots of attachments will use your limits faster. A portion of your limit resets every 4 hours as well. Your average message in this thread is costing ~20 cents. There is a limit to how many of those you can do on an $8 subscription.

                            • Mark Florkowski

                              Team

                              Starting a new chat and not attaching a bunch of files again is the only thing that will help. You can still continue the conversation, but requests will use your limits faster, and output quality might not be as good. It is generally best to provide the minimum possible context to the model, so it does not have to both “figure out” what is important information, as well as generate the response.