Which tool to choose
The upload error depends more on your environment than on the assistant, but changing context sometimes solves it on its own.
- If you upload from the browser, the most frequent culprit is the extensions: ad blockers, privacy tools, and VPNs interfere with the upload. The "incognito" window (a browser session with no active extensions) is the quickest test.
- If you upload from the app on the phone, the suspicion shifts to an unstable connection or permissions: the app might not have permission to access photos and files. This has to be checked in the phone's settings.
Before switching assistants, try switching environment: same file, clean browser or different connection. Often the problem disappears without touching anything else.
How to do it
Proceed by elimination, from the quickest remedy to the most laborious.
- Reload the page and try again. A stuck upload is often a momentary hitch: reloading resets the state and the second attempt succeeds.
- Open an "incognito" window of the browser (in the browser's menu, the item for private browsing) and try there. In incognito the extensions are disabled: if the file goes through, you've found the culprit.
- If it works in incognito, go back to the normal window and disable the suspicious extensions one at a time (ad blocker, privacy, VPN) until the upload starts working there too.
- Check the format. The AIs accept the common formats (PDF, JPG, PNG for images; PDF and Word for documents). A strange format has to be converted first. The operational syntax to ask the AI itself:
I want to upload a file in [write the extension, e.g. .heic] format.
Do you accept it? If not, into which common format should I convert it first,
and how do I do the conversion?
- If the file is large, shrink it: compress the PDF or resize the image with a free online service (search "compress PDF" or "reduce image size").
- Feedback: after the file has gone up, the proof is the attachment box with the file's name clearly visible and fixed. If it appears, the upload succeeded.
A concrete example
Sofia tries to upload a photo of a bill from her phone and gets a generic error. The photo is in a format the AI doesn't like, because her phone saves images in a proprietary format.
She opens the photo in the gallery, shares it choosing "save as JPG" (or takes a screenshot of the photo, which turns it into a standard format), and uploads that version. The upload succeeds. The problem wasn't the size or the connection: it was a format that just needed converting with one step.
When it does NOT work (and how to fix it)
If the upload always stops halfway
Almost always it's the file's size or the connection. Try with any small file: if that goes through, your file is too large and has to be shrunk. If even the small file fails, it's the connection: switch to a more stable network or try again later.
If the error says "format not supported"
The AI is telling you it can't read that kind of file. Convert it into a common format: images into JPG or PNG, documents into PDF. There are free online converters for almost every format; search "convert [starting format] to PDF." A screenshot, for images, is the quickest conversion of all.
If it works in incognito but not in the normal window
The culprit is a browser extension. Disable them in groups and try again, starting with those that intercept traffic: ad blocker, browser antivirus, VPN, privacy tools. When the upload starts working, you've isolated the extension that was blocking it.
If the app on the phone won't upload photos
Check the permissions: in the phone's settings, under the AI app's entry, verify that it has permission to access photos and files. Without that permission, the app can't take the image from the gallery. Grant the permission and try again.
A tip from someone who actually uses it
When an upload gives an error, don't waste time guessing: start from the incognito window. In thirty seconds it tells you whether the problem is the browser (it works in incognito) or the file itself (it fails there too). That test divides the world in two and tells you right away which side to look on, instead of disabling extensions at random hoping to guess right.
Frequently asked questions
Why did the same file upload yesterday but not today?
Often the environment changed, not the file: an update to a browser extension, a VPN that activated, a weaker connection. The incognito test tells you whether it's the browser. If it fails there too and it worked yesterday, try again later: sometimes it's a temporary hitch with the service.
How do I find out how large my file is?
On the computer, right-click on the file and look at "Properties" (or "Get Info" on Mac): you'll find the size. On the phone, the file's or photo's information shows it in the details. If it's in the order of many megabytes, it's worth shrinking it before uploading, because heavy files fail or stall more often.
Does converting or compressing a file ruin its content?
Compressing a text PDF doesn't ruin the text. Compressing an image too much, though, can make it grainy: if the AI has to read text inside a photo, don't compress it to the bone or it'll become unreadable. For images with text, it's better to reduce only enough to let them through, keeping them sharp.
If none of these remedies work, is it the AI's fault?
Rarely, and that's the conclusion not to jump to too quickly. When you've tried a clean environment, a common format, and a reduced size and it still fails, before blaming the AI try the route that skips the upload entirely: paste the text if it's a document, or describe the image if it's a photo. If that works, the problem was the upload channel, not the AI. And often, in those minutes lost reloading, pasting the text would have been the shortest path from the start.