hmmmm wait a sec then. Cutting in very hard can destroy this trick as well. Not trying to analyze everything you say, but just trying to get an understanding since you don't have a video.
You should be able to complete this trick by only going about 5 feet outside the wake. I can take these bigger and smoother by cutting out a measily 5 feet outside the wake. Then start edging back in. However, the closer I get, the harder I lean back away from the boat as my edge is also going the opposite way. Remember, keep that handle low all the way thru the trick. By the time I release off the wake, i'm almost edging at a 30 degree angle away from the boat (the other way).
Now, I've seen lots of people to this day trying backrolls out behind my boat or on the lake in general. Most of the time the edge hard into the wake, then try and huck it at the last minute. OR, edge straight in (not away from the boat at the last minute) and the rope always snaps out of their hands or lead hand.
I always let go half way thru the trick with my back hand. As I come thru the invert and see the water, the rope is in my lead hand already with tension and it's as smooth as ice.
You could be coming into the wake too fast if that makes sense.