Well Plugman permanently disabled a plugin. (https://www.spigotmc.org/resources/%E2%98%9B-boss-unbelievable-custom-monsters.46497/)

I used /plugman reload on advanced respawn, a plugin that has nothing to do with the plugin in question which is boss and now unless I use "/plugman unload Boss" and then "/plugman load Boss" , that plugin will stay disabled, no matter how many times I re-install it. There is nothing on the console.

This is really annoying because it means that if the server auto restarts, that plugin won't be enabled.

I found out it one of the bosses had something to do with biomes, preventing the plugin from working and thus has been fixed.