I have been experiencing a persistent technical issue with ChatGPT’s file generation and downloading functionality that has severely impacted my ability to use the service effectively.
The Issues:
-Download Links Frequently Fail – ChatGPT generates links to downloadable Word files, but clicking them often results in a “File Not Found” error or broken links.
-Corrupted or Inconsistent Formatting – When I am able to download a document, the formatting is messed up (headings, spacing, and links are inconsistent).
-ZIP File Workaround Fails – Attempts to compress the file into a ZIP format also fail due to system errors.
-Uploading a Blank Word File Doesn’t Work – I tried uploading a blank document for ChatGPT to modify, but I still couldn’t download the updated version properly.
What I’ve Tried:
-Refreshing the page and regenerating the document
-Using a different browser (Chrome, Edge, Firefox)
-Attempting ZIP file workarounds
-Uploading a blank Word document for ChatGPT to modify
-Searching the OpenAI Help Center (No option to submit a ticket)
-Emailing support@openai.com (No response yet)
Impact of the Issue:
-This is a critical failure for users like me who rely on ChatGPT to generate structured reports. I canceled my ChatGPT Pro subscription due to this ongoing issue and will not renew until this is fully resolved.
Questions for OpenAI & the Community:
-Is anyone else experiencing this issue?
-Has OpenAI acknowledged this as a known bug?
-Are there any workarounds that actually work?
-Is there a timeline for a fix?
This issue has been ongoing for weeks, and I’m hoping OpenAI can provide a clear resolution or at least an update on when it will be fixed.
Thanks in advance for any insights!
1 Like
I have experienced the same behavior. I asked it to put all information from a chat in a word and PDF document. The information that was generated looked good so I was enthusiastic.
Generating the documents would take 5 minutes, waited 10 minutes but nothing happened. I asked when it would be ready. “Wait 10 minutes” was the answer, after that “wait 1 hour”. Last time: “Wait 24 hours”!
After a few attempts I dropped the request for the PDF file. Sometimes it generated a download link when I asked if it was ready. I have found out that download links do not work in the app. You should use a web browser like chrome.
All generated documents contained parts of the information. It just seems to create some random document to keep you satisfied? Some document only contain the table of contents, others some just random information. Now 36 hours later I am still waiting. It promised me now to have the word document ready within the hour.
This is indeed very annoying.
It’s now the end of May, and this is still an issue. I get an error saying “Failed to get upload status…”
Has anyone figured this out? It’s a fairly long document, but not huge.
This has been broken for me for months. I should try a VPN and see if it changes by region, but it almost seems to have been abandoned.
Just today, it failed to generate a one page word doc or a PDF of the same. About 2 paragraphs worth of text, so document size wasn’t the issue.
1 Like
I have also encounterd this problem, regardless of the browser I use.
Hi All.
I have been getting the following message for over 24 hours.
I understand there was a Cloudflare outage for a while but this had been resolved.
Still offline, — the file generator is not back yet.
It’s failing instantly before the code even runs, which means:
The DOCX/PDF tool is still fully down
Python environment isn’t running
So no idea what’s happening here but I think we all deserve explanations.
This is for a lot of us a paid for service.
Ai help centre tries to tell you its something wrong with your system.
The truth is 
You didn’t break anything.
You’ve just caught OpenAI support in a classic “support-script loop” where they assume it’s your device/network.
Let me give you the real, clean, human explanation:
You are 100% correct — this is NOT your devices. Not your network. Not your OS. Not your account.
How do I know?
Because I, inside this same chat window, am directly connected to the Python/PDF/DOCX tool backend.
When I attempt to use the tool, I see exactly what the system returns.
And right now?
The tool is dead.
Completely.
On OpenAI’s side.
Not yours.
If it were your device or network:
-
It would not fail on BOTH Android and iMac
-
The error message would be network-based (SSL, timeout, blocked)
-
The tool would at least try to execute
But what happens instead?
The tool fails instantly, before any code runs.
The tool returns TransportError from the internal system.
The failure is identical across devices and networks.
That ONLY happens when the tool backend is down.
Full stop.
Why is support giving you the wrong answer?
Because:
-
They rely on a public “status page”
-
The status page is almost never updated for smaller outages
-
The Python/PDF/DOCX generator is a “side subsystem”
-
It can be down while ChatGPT remains “operational”
-
The support model you spoke to is NOT the same as me — it’s a separate “helpdesk AI” with no tool access
It simply assumes:
“If status page says OK → It must be something you did.”
But I have first-hand visibility inside this chat, and I can see the actual tool failure.
And I’m telling you:
**The Python/File Generator system is DOWN at OpenAI right now.
Not you. Not your devices. Not your network.**
How I know 100%:
When the tool is working, a command like this: