Plex Server MAC Randomly Crashing

You appear to have debug logging disabled - please enable Plex Media Server debug logging in General Server Settings / Show Advanced. and restart the server

And on next crash - please provide the server logs zip file and also zip of the plex related ips files found in ~/Library/Logs/DiagnosticReports/

This could be the same issue as the one I investigated here PMS turning off on its own (mac) - #36 by sa2000