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