I had a 2 man boat with a trailer with rollers instead of bunks. If I had ever unhooked the winch strap before getting the boat backed into the water the boat woulda rolled off the rollers and hit the dry ramp. My boat would roll back down the trailer before I could get up front (when loading) to hook up the winch strap unless I left it in gear and running (which is something I really didnt like doing with a tiller controlled motor). I dont know if it would work with your boat, but I'd suggest changing those rollers out for bunks. I did and that fixed all my problems.