Multiple PLEX Servers - Can't access them all at the same time anymore

[OttoKerner]

@Qwinn

But what happens is, authorized devices only shows one of them at a time, and whichever I restarted last is the one whose hostname appears under Authorized devices. It just seems to replace the one claim/registration with the other.

Did you clone the first server to create the second one? i.e. copied all the plex data folder over?
If so, the two servers have identical machine IDs. As soon as one of them is restarted, it contacts plex.tv and overwrites the URL of this machine ID.
You need to separate the two machines: Moving/Cloning Metadata - #4 by OttoKerner
(Replace any mentions of the Windows registry with the file Preferences.xml if you have a NAS or Linux server.)