Alright I need some help moving my Plex server from windows to Linux and maintaining the same library. Would gladly pay 100k sats for the help.

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Oooo mmmm, its my work week, what parts do you need help with? The library itself isn't your movies, those are just files you can move over, and the library can be rebuilt by selecting which folders they are stored in.

I'm following the guide here: https://support.plex.tv/articles/201370363-move-an-install-to-another-system/

But when replacing the server data in var/lib... with the data from the windows machin, the Plex server will no longer start on Linux.

I've already got the drive with my media moved to the same machine and mounted with the proper permissions. I can use Plex fine with a fresh install but I need to move all the data from my old server library. There's a lot of curation I've done.

Did you already include all the cover pictures and stuff for the movies? If so Plex should really do the rest.