You need to setup /etc/crypttab to unlock the disk: https://linux.die.net/man/5/crypttab
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I used GNOME Disks to modify /etc/crypttab and /etc/fstab to auto decrypt and auto mount on boot. Jellyfin still loses its access each time I restart, even though the jellyfin group still displays having access to the files.
Edit: Turns out it does have access, but it's no longer under the /media/username directory. I have to point Jellyfin to /mnt/UUID instead. This fixed it!
What changes were made, exactly? Not everyone has a desktop environment on their server.
Thanks for editing in the solution!
What filesystem are you using on the external drive? If it is NTFS or FAT, they won't store permissions on the filesystem, which would explain why the owner/group changes are not persistent. To fix that, you can set the uid/gid on mount in your fstab.
/dev/mapper/YOUR_DRIVE /path/to/mnt <fstype> rw,uid=<jellyfin_uid>,gid=<jellyfin_gid>,dmask=0002,fmask=0113
I bet it’s because it’s encrypted. Idk if there’s a fix to that. I had a lot of trouble making local servers auto unlock when using LUKS.