LuckPerms completely breaks
CrazyCrates stop working
DeluxeMenus "half" works. Every third time or so you try to click something in a menu, nothing happens.
CrazyEnvoy just says "OnGoing"
Genbuckets (custom plugin) stops working
RandomTP plugin breaks
Players warping without instant TP just can't teleport anymore.
MoneyPouches break

As soon as I remove LuckPerms, everything works.

Here is an error I run into: [Server thread/INFO]: com.mojang.authlib.GameProfile@3b26ccb8[id=74d5cf6f-c583-4767-8c25-009ea2811b52,name=Greers4,properties={textures=[com.mojang.authlib.properties.Property@457f2a73]},legacy=false] (/197.**.***.***:*****) lost connection: §7§l[§b§lL§3§lP§7§l] §cPermissions data could not be loaded. Please try again later.

I am using the latest version of LuckPerms, PaperSpigot 1.8.8

Please upload a copy of your servers most recent log file to https://gist.github.com/ and reply with the link.

https://gist.github.com/pinchcraft/0b4b71ff2f892f56a98c22e6fc277164
Thanks for the fast response :P

Those failed login attempts were most likely because those players started to connect before LuckPerms had enabled.

I don't see how everything else is supposedly breaking because of it? Players were able (from looking at the log) to join as soon as the server had fully started.

Yes, at me too, there is not always work this or that plugin or the permission. I have to redistribute the group to the player and then everything is fine.

What is that? https://hastebin.com/muluxarava.md

Try updating to the latest version.
https://ci.lucko.me/job/LuckPerms/