Photo upload on iOS stops after the first photo

This is the first time I am setting up Camera Upload via the Plex iOS app. I created the photo library (but no album) through the app, and attempted to manually upload the photos. After the first photo gets uploaded, the upload stops and I cannot get it to restart uploading.

I have the newest version of PMS (Version 1.8.4.4249) and the iOS app installed.
I replicated the issue and generated the attached logs.
Let me know if any additional info is needed.

On searching a little more in the forums, I see a bunch of posts were related to permission issues on Linux/FreeBSD.
I have my PMS running in a jail on FreeNAS and checked the file permissions for the relevant folders starting with Media Upload.

drwxr-xr-x 3 plex plex 3B Sep 10 21:33 Media Upload

The Library directory that is created within Media Upload.
drwxr-xr-x 3 plex plex 4B Sep 9 14:36 Mobile Uploads

The single photo that got uploaded in Mobile Uploads.
-rw-r--r-- 1 plex plex 3.3M Jun 15 2009 2009-06-15 10.21.49.JPG

I suspect the permissions may be fine since at least one photo got uploaded, but not sure.

I also uninstalled/reinstalled the iOS app and tried the upload step again as that seems to have worked for some users, but didn’t work for me.