Access lost to server even though it is running

In your account, I see four servers with the same name. This tells me the server has been recreated (at least Preferences.xml) from scratch four times.

Given you moved to a NEW ubuntu installation, I suspect you have a new SERVER ID again.

Sharing is on a Server ID basis (stored in Preferences.xml) .

Go into Settings - Users & Sharing (upper left). Everyone is still there.
You just assign them again to this new SERVER ID.

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There are easy ways to prevent this from happening but takes a little planning upfront.
( Moving PMS is detailed in Linux Tips How-Tos

  1. When installing the OS, make a /home partition
    – OS is 64 or 128 GB (I use 128)
    – Swap is 16 - 32 GB
    – Home is the rest of the volume (unless an SSD you want to carve up further / finer)

  2. Install PMS and get it initialized

  3. Stop PMS and create a new home for it on the /home partition
    – mkdir /home/plexmediaserver
    – chown plex:plex /home/plexmediaserver
    – using ‘tar’, copy all of /var/lib/plexmediaserver to /home/plexmediaserver

sudo bash
cd /var/lib/plexmediaserver
tar cf - . | (cd /home/plexmediaserver ; tar xf -)
  1. Create a systemd override to change the Envirionment="PLEX_MEDIA_SERVER_APPLICATION_SUPPORT_DIR=/home/plexmediaserver/Library/Application Support"

  2. After this is complete, PMS is now kept safe (stored independent of the OS) on the /home partition ; which you’re not forced to erase should a fresh OS install be needed…