Castiel might be many things in this episode, but he clearly still does’t like Dean torturing. brb gonna go cry in a corner.
Look at “On The Head Of A Pin”, where Castiel says “I would give anything not to have you do this”
and then look at ”The End”, where Castiel’s given everything, and it still wasn’t enough; Dean still has to do ‘this’.
and then look at that second gif and tell me that doesn’t rip him up inside