I’ve been having the same issue on my iPhone for months. Just been dealing with it and loading pics one at a time.
iPhone 12
IOS 17.5.1
Which browser?
Safari
Just tested our home upload speed. 180Mb/s.
I used to think it was a bad cell connection, but even fast WiFi has the same problem.
We only have Apple devices.
I had a similar issue yesterday on Safari on both my iPhone (iOS 16.7.2) and MacOS (latest version of MacOS 13).
Tried to upload 5 photos at once. Website started the update, would still at ~36% uploaded, and then error out.
After trying this multiple times, I uploaded fewer photos at a time w/o issue.
Based on what @js76wisco experience, maybe it’s something about iOS/MacOS, Discourse, and # of files?
I literally can do one file and even that took 3 tries today. I use safari iPhone either fiber based Wi-Fi or data
It used to be better but something seemed to have happened about a year ago
I can confirm switching from Safari to Chrome on my iPhone doesn’t help. HEIC vs JPEG also doesn’t seem to matter. Doesn’t matter if images are in photo library or somewhere else.
Yikes. 
I post exclusively from my phone using Safari. The only issue I incur is the 5 photo limit before it errors out.
If you do one at a time with captions in between…never an issue.
But sometimes you just wanna photo dump.
My iPad is running 15.4 so maybe there’s an issue with a more recent version. I’ll update it and try to reproduce the issue again.
yeah one by one no issues. more than 1 (even 2-3) sometimes has issues
I updated my iPad to iOS 17.5.1 and a three-file upload failed after the second with the following error:
/var/www/discourse/lib/discourse.rb:138:in `exec':
Seems like Discourse has fixed the photo glitch. I did a trial run and uploaded 5 photos in seconds.
Yep that’s what I do. Click on that and it links to my photo album then I select and upload photos to my report. Easy-peasy.
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Yep I just uploaded five photos at once for the first time in a long time.
I guess my reporting the bug and narrowing it down to recent versions of iOS were worth the effort.
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