That is what appears to be happening as can be seen in the logs
You probably have a scheduled task starting Plex Media Server.exe as well as it is starting by default on launch
You had 2 instances of Plex Media Server.exe processes running in parallel at 16:51:34
Normal auto launch of PMS (Plex Media Server.3.log)
May 19, 2021 16:51:34.126 [10624] INFO - Plex Media Server v1.22.3.4523-d0ce30438 - Microsoft PC x64 - build: windows-x86 windows - GMT -05:00
Scheduled task launch of PMS (Plex Media Server.4.log)
May 19, 2021 16:51:27.874 [9476] INFO - Plex Media Server v1.22.3.4523-d0ce30438 - Microsoft PC x64 - build: windows-x86 windows - GMT -05:00
and again from 17:19:57 - two parallel instances running
Normal auto launch of PMS (Plex Media Server.log)
May 19, 2021 17:19:57.008 [8580] INFO - Plex Media Server v1.23.1.4528-c0513eb4c - Microsoft PC x64 - build: windows-x86 windows - GMT -05:00
Scheduled task launch of PMS (Plex Media Server.1.log)
May 19, 2021 17:19:49.936 [8120] INFO - Plex Media Server v1.23.1.4528-c0513eb4c - Microsoft PC x64 - build: windows-x86 windows - GMT -05:00
Suggest you remove the scheduled task and just have auto launch
Or alternatively look into using this add-on product: PMS as a service - General / Tips, Tricks & How-Tos - Plex Forum
