Rolling/sleeping

My son is 5 months old tomorrow. He’s been rolling belly to back for awhile now but hasn’t quite figured out how to roll all the way from back to belly. He gets his arm under himself and can’t quite get the extra push to get past that. Trying to get him sleeping in his crib but it’s been difficult because he’s started trying to roll as soon as I lay him down, then gets mad that he can’t do it. He eventually settles down and ends up falling asleep partially on his side. This is a problem too because then he naturally drifts back to his back and it startled him and wakes him up 🤦🏼‍♀️

Does anyone have any advice for helping him learn to get past that arm under him and roll on his own? I think once he can do it he’ll probably roll to his belly and sleep better.