Ahhhh, if I didn't know how frustrating it can be I would say it is actually quit funny.
I waited "too long" to transfer DD to the cot. By then she could stand, so she would just get straight back up again and scream. The only way I could get her to sleep in her cot was by putting her to sleep in my arms or in my bed first and then transferring her once she was asleep. But if she woke up, I had to do the same thing again.
She started fighting the wrap at about 3 or 4 weeks. She always wanted to get her arms out and if she couldn't do it, she got frustrated and started crying.

I'm not much help, but I think you should let him roll if that's what he wants. In my eyes, wrapping is meant to give security and coziness, not be a straight jacket to force them to sleep. if it doesn't feel good to him anymore, it's time to find something else. He will eventually get used to rolling and not do it when he wants to sleep. But you mgith be in for a few rough days.

Hope it all goes well.
Sasa