Sleepyhead to cot side sleeper

[Lovingtyrells]

My baby boy is 6 months and doesn’t sleep... anyway for the rare time I can transfer him into the sleepyhead he is kind of wedged in on his side.
Not sure how to move from this to the cot.

He is trying to roll now and therefore although having him wedged in to stay asleep after the transfer is good, he is clearly uncomfortable and trying to wriggle which increases the wake ups even further still.
When I’ve tried to place in the cot he tips over immediately moves arms and wakes, tried also with a blanket rolled up but doesn’t work. Any ideas ? ( he has never slept on his back - reflux baby )

Does he sleep on his front? With Ds1 (the great non sleeper/difficult transfer) his sleep improved a lot when he started sleeping on his front. I would put him in the cot and kind of roll him onto his front away from me, then put a firm hand on his back til he settled.

Otherwise, it may be time to start putting green him in awake and settling from there.