Hey metaphalanx1 — that infinite loading wheel on image upload is frustrating, and you’re right that reloading-and-reattaching kills your flow. A few things that reliably help, plus the right way to get it actually fixed.
Workarounds you can try right now
Shrink the image before attaching. This is the most common culprit — very high-resolution screenshots (several MB) often hang the uploader. Compress or resize them first and they usually go through on the first try.
Attach one image at a time. Uploading several at once is far more likely to stall than doing them one by one.
Check the format. Stick to standard PNG or JPG. Exotic formats (iPhone HEIC, WebP, huge captures) are the most likely to choke.
Look at your network. A flaky connection or an active VPN makes the upload retry in a loop. Try without the VPN / on a more stable connection.
Clear cache or switch browser. A plain reload isn’t always enough — a real cache clear, an incognito window, or a different browser (Chrome ↔ Firefox) often unblocks it.
Use desktop instead of mobile. Uploading from a mobile browser is noticeably more fragile than from a computer.
Fallback: host the image and paste the link. Instead of attaching the file, upload it somewhere with a public URL and paste that link into your prompt. The agent can usually read the image from the link, which bypasses the stuck uploader entirely.
How to get it actually fixed
This is a bug in the Replit tool itself (the chat uploader), not in your app’s code — so the real fix has to come from Replit. To help that happen:
Document it precisely in your post: browser + version, OS, mobile or desktop, the size/format of the images that hang, since when (you mention ~1 month), and whether a VPN is active.
Open a support ticket in addition to this forum post. The forum helps the community; a ticket puts it on the team’s radar to be traced and fixed.
The more specific your repro details, the faster someone can pin it down. Hope one of the workarounds gets you unblocked in the meantime.