As the title say i wonder what have you as a player or as a GM thrown at your group that would/did break them ( end game stuff )
Like have anyone thrown the kraken from Tome of Blood
Recreated the Skull Harvest
Thrown high end demon princes or greater demons at a low-mid game party
Personaly worst i fought was a bunch of mechanicus dudes and a Onager deamon engine of wich our heretek forced it into lava.