The plugin should have a way to resume its operation after a server restart.

The Trim task finishes quickly enough that there's no purpose in saving and resuming it. The Fill task has featured saving and resuming itself on server restart since it was implemented years ago, barring the server completely crashing and not exiting properly.

So.... what are you talking about?

The server fill command never resumes after a restart in any of the three servers I have this on. Could be something with the server but considering there isn’t really a config I don’t think so.

It sounds like maybe you aren't properly shutting down your servers using the stop command and are instead just killing their process or something similar.

the process I use is the restart command in paper it shuts down the server and runs a script I programmed to launch the server

Well, no idea what's going wrong on your end.