Following your post here, I checked your last set of logs and you have the symptoms of tcp port exhaustion issue
Jun 08, 2020 23:09:19.099 [16512] ERROR - [Transcoder] [tcp @ 02efde80] Connection to tcp://127.0.0.1:32400 failed: Error number -138 occurred
Jun 08, 2020 23:09:19.144 [12108] ERROR - [Transcoder] [tcp @ 02d5b780] Connection to tcp://127.0.0.1:32400 failed: Error number -138 occurred
If you open your windows event logs with “Event Viewer” and filter the “System” event log for event Id 4227, you can see how often it is happening
If you filter on 4227,6005 that will show reboots and tcp failures due to running out of dynamic ports.
Safest option after getting a 4227 is to reboot windows.
Once you run out of tcp ports then things start to fail
Plex Media Server scanning of large movies libraries (greater than 4000) or analyzing TV Shows library with thousands of episodes have been seen to result in this. It is a curl bug that came in when we upgraded curl in Plex Media Server. A fix has already been produced and we are waiting for the new version of curl to be available