Plex Media Server is unavailable after every reboot

Server Version#:Version 4.148.0
Player Version#:?
<If providing server logs please do NOT turn on verbose logging, only debug logging should be enabled>

Every time the PC where my Plex Media Server lives loses power, the PMS can’t be found. “Jef’s Win10 Box is unavailable”. I select Retry connection, no change. I have disabled my security software (TrendMicro Maximum), no change. I’ve added Plex Media Server (along with several other Plex related apps) to the list of apps allowed through Windows Defender. I’ve tried adding PMS to the list of Bypass VPN in the split tunnel setting of my VPN Client (Private Internet Access). I’ve upgraded the PMS version each time. The Plex app won’t connect to my PMS unless I go into my downloads, and reinstall the .exe. Then I can refresh the browser and see my media, and I can check the PMS settings. I’ve followed the steps on the troubleshooting links, but I can’t seem to make this desktop stop deleting my Plex Media Server each reboot

Instead of reinstalling, have you tried to start Plex media server via the regular Windows Start menu?
If that works, it is merely a matter of adding Plex server to the Autostart items.

I think we’re on the right track…After rebooting, I again saw Jef’s Win10 Box is currently unavailable again. Through the start menu, I ran the PMS app, refreshed my browser, and it immediately came online. Looking in my startup menu though, I saw PMS was already set to On. I tried toggling it, and rebooting again, …is currently unavailable.

So I guess my problem/question is, how to I make Windows actually start the server automatically like it did for years up until a few months ago?

Check if the current item in Autostart is pointing to the 32bit binary location, which is by default in C:\Program Files (x86)\... There is no 32bit version of Plex server anymore, so it is now by default in C:\Program Files\...

After starting Plex server manually, seek out its task tray icon.
Right-click on it.
Remove the check mark from “start automatically”
Then put the check mark in again.

I appreciate all your help with this. I posted the same question on Reddit, and found a solution. Once the PMS was running, I right clicked it in the System tray - and saw “Start Media Server at Login” was unchecked. Checked it, rebooted, and now it runs on startup as it should.

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