Some ChatGPT users report 'Unknown error occured' when uploading files

Update 20/05/26 – 21:20 pm (IST): Today, we are again seeing reports of the same issue. Here’s a screenshot showing some fresh reports:

However, OpenAI hasn’t yet updated their service status tracker page. Meanwhile, try zipping the files and then dropping them, as this seems to have worked for at least a couple of users. Anyway, we are keeping an eye and will update the article as and when we come across anything newsworthy.

Update 11/05/26 – 09:19 am (IST): OpenAI officially acknowledged the widespread file upload problem earlier this morning. Their engineering team has already applied a mitigation to fix the elevated error rates across the platform. They are currently monitoring the recovery process to ensure the service stabilizes for all users.

While waiting for a complete resolution, many users discovered temporary workarounds to get their files uploaded successfully. Compressing documents into a single ZIP archive or switching to the mobile application appears to bypass the errors. Normal functionality is expected to be fully restored shortly.

Original article published on January 29, 2026, follows:

Some ChatGPT users have been running into a frustrating file upload problem today. When trying to attach PDFs, documents, or other files to their conversations, many are getting hit with an “Unknown error occurred” message that blocks the upload entirely.

Multiple Reddit threads popped up within the past few hours reporting the same issue. One user on a MacBook tried everything to fix it. They cleared cache and cookies, restarted their computer, tested incognito mode, switched browsers, and even tried a different device. The files uploaded just fine on another computer, pointing to something weird going on with specific setups.

Several Pro and Plus plan users confirmed they’re seeing the error, while one user noted their free account worked perfectly fine with the same files.

The problem started around 4 to 5 hours ago, based on user reports across multiple discussion threads. Some users found that zip files would technically upload, but then ChatGPT couldn’t actually read them. The AI would show a thinking process saying the /mnt/data directory appeared empty even though files were supposedly there.

One MacBook user discovered a temporary workaround by emailing files to themselves, downloading them on their phone, and uploading from mobile instead. Others reported success after compressing multiple files into a single zip archive.

What’s strange is that OpenAI’s official status page isn’t showing any ongoing issues right now.

ChatGPT is also facing issues with the model labels disappearing for Plus subscribers, as we reported earlier. So it’s clear that the company needs to work on addressing these problems affecting paying customers. Since this seems like a server-side problem, it’ll likely be fixed sooner rather than later. We’ll update the article if and when there are any further developments.

Featured image credits: u/yesluck / Reddit

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