Camera Upload sees items waiting to sync but never uploads them

Hello,
I’m having issues with doing an initial sync on my server. The server is on the latest Plex Pass version for Windows. iOS app is latest as well. My iOS app stops at 127 items left to sync. When you start the app, the app scans the library and seems to know that it’s missing 127 of the 939 items. When you enter into the Camera Upload section, the status goes from scanning the library to “Downloading data from iCloud” and gets to 99 or 100% on the next file (a video file). Once it’s done with the download, it goes immediately to “Waiting to upload” state and doesn’t change to the Uploading state.

I looked around and some other people had issues with burst images or live images. The images waiting to be uploaded aren’t anything like that. I even took a screenshot to make sure it had something to upload that wouldn’t cause issues, the problem still persists.

What can I do to debug this issue?

Not sure what the issue was, but I was able to solve it by deleting the movie, exiting the app, and the entering the app again to restart the syncing process.