PMS doesn't scan on startup

Shouldn’t it do that automatically? Or do I have to hit on the “Update Libraries” every time?

No, it shouldn’t start a library scan on startup.
Why should it do that?
Plex server is intended to run 24/7.

Why? Because even Kodi can do such a basic function. Or any music player.

Plex server is not a player. It’s a server. It is not intended to be only started when you want to play something. As I wrote above, it is intended to be run around the clock.
It does perform a daily maintenance cycle, which can include library scans if you tell it so.

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