Rolling at nap/bedtime?

My 5 month old started rolling from back onto his tummy then freaks out because he’s on his tummy and can’t get back. He has rolled from his tummy to his back but hasn’t in a while. I keep flipping him because he’s upset and eventually he falls back asleep. I can’t remember how we dealt with this for our daughter 😔

I know I can leave him and there’s nothing else in the crib but how can I get him to adjust better to either sleeping on his tummy or stop rolling?