Crib transition

I'll rock my LO to sleep and try to transfer him to the crib but he wakes up every time his head touches the mattress 😭 I've tried to put him in there when he's almost asleep too and the same thing happens, eyes wide open! He won't sleep in there at all! I try multiple times in a session, usually an hour and a half total before I give up trying to get him to sleep in there. Any advice would be appreciated !!!

(Also this is for naps and also bedtime)