Have you signed into your plex account on the server? Free accounts are fine.
You say:
"I also checked the transcoding folder in question and confirmed it is mounted executable."
I do not know what you mean by this. Please clarify. Post your container volume assignments.
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From the container log...
[s6-init] making user provided files available at /var/run/s6/etc...exited 0.,
[s6-init] ensuring user provided files have correct perms...exited 0.,
[fix-attrs.d] applying ownership & permissions fixes...,
[fix-attrs.d] done.,
[cont-init.d] executing container initialization scripts...,
[cont-init.d] 10-adduser: executing... ,
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GID/UID,
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User uid: 1000,
User gid: 100,
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[cont-init.d] 10-adduser: exited 0.,
[cont-init.d] 40-chown-files: executing... ,
[cont-init.d] 40-chown-files: exited 0.,
[cont-init.d] 50-gid-video: executing... ,
[cont-init.d] 50-gid-video: exited 0.,
[cont-init.d] 60-plex-update: executing... ,
Docker is used for verisoning skip update check,
[cont-init.d] 60-plex-update: exited 0.,
[cont-init.d] 99-custom-scripts: executing... ,
[custom-init] no custom files found exiting...,
[cont-init.d] 99-custom-scripts: exited 0.,
[cont-init.d] done.,
[services.d] starting services,
Starting Plex Media Server.,
[services.d] done.,
when I say executable I'm saying I set permissions read/write/executable on those folders. I attached pictures and hope this is helpful?
Yes, I did sign out and back in multiple times and every time it will not let me claim server.