Hello, it is my belief that the way your plugin is coded that sometimes the server fails to restart. I'm running git-Paper-321 and DiscordSRV v1.18.4.
I notice I often have to interact with the console for the server to fully shutdown.

Plugins (22): AsyncWorldEdit, AutoRestart*, ChopTree2, ClaimslistClassifier, DiscordSRV, dynmap*, Dynmap-GriefPrevention*, Essentials, EssentialsAntiBuild, EssentialsChat, EssentialsProtect, EssentialsSpawn, GriefPrevention, LuckPerms, MineableSpawners, OreAnnouncer, ProtocolLib, SnowDrift*, SnowierSnow, Vault, WorldEdit, WorldGuard

(world saves)
...
[19:56:20 INFO]: Flushing Chunk IO
[19:56:20 INFO]: Closing Thread Pool
[19:56:20 INFO]: Closing Server

[19:56:41 ERROR]: [DiscordSRV] Could not send message to channel TC:server(690273186977153191): The Requester has been shutdown! No new requests can be requested!

Is it on a panel like Multicraft or Pterodactyl?
By "interact" do you mean like sending a command or?

Just disabled... Will re-open if issue doesn't resolve itself

This isn't a cpanel but rather a command line console window. (in this case powershell)
java -Xms21000M -Xmx21000M -jar paper.jar -nogui --nojline
By interact I mean if i type a command or just hit enter the console proceeds. It's like java isn't closing until it's prodded.

That to me sounds like the powershell window is in "select mode" (or "QuickEdit Mode") (when you click inside the window it tries to select characters), and pressing a key is taking it out of select mode