[Windows 10 Update KB4338819 issue] Conversion Failed. The transcoder exited due to an error

Thanks for the feedback. You have disabled debug logging, Could you please:

Ensure debug logging is enabled
see https://support.plex.tv/articles/201643703-reporting-issues-with-plex-media-server/

Restart the server to get fresh log files created

Reproduce the problem
Note down the time of error and what was being streamed

Download the logs
See https://support.plex.tv/articles/200250417-plex-media-server-log-files/

Attach your logs zip file to a post here with info on when the error arose and what plex client app and version was being used

PS: Are you running Plex Media Server.exe as a scheduled task / service?

Using the cjmurph’s packaged service wrapper would stop these repeated log system tray related log warnings
See PMS as a service