Transitioning out of swaddle

peacelove&mama

I've posted here a few times in the past but I lurk mostly.

I have an almost 5 month old son who up until now has been sleeping swaddled. He was never much of a sleeper without it, but wrapped up he was STTN. Lately he's been waking but I attributed that to the 4 month wakeful.

I need to teach him to sleep without being swaddled because he has started rolling onto his belly and getting stuck. I tried one arm out earlier, thinking he would do better that way and it would make for an easier transition, but same thing, he got stuck and freaked out. Basically as soon as I lay him down, he rolls and/or he starts flailing. He'll fall asleep on me in the rocker no problem, he just wakes up as soon as I try to put him down.

I've tried shushing and patting, rubbing his back, holding his hand, singing... None of it seems to help. He just keeps fussing and eventually escalates to crying, and I just can't bring myself to let him cry.

Any suggestions on how I can help him learn to sleep in his crib without being swaddled? I know I'm going to be in for some rough nights, but I'm totally at a loss. My older son was an amazing sleeper from the start, but this one is the polar opposite.