Hi David, Been there: done that too. When I first got my M15, the aft mast carrier was a 2 x 4, and as I later determined, the original stainless steel mast support had been cut off. Trying the raise my mast for the first time, I had the reverse of your problem. The mast hit the edge of the companionway hatch, and the heel was too high to insert the mast bolt. So, the answer was, the aft end of the mast had to be raised so that the steeper angle allowed the mast heel to be in the right position, and not hit the edge of the CLOSED companionway hatch. (If the companionway hatch is open, then the aft end of the mast has to be still higher so that the mast clears the companion way hatch edge). Doing some re engineering, I built a new trailering mast support that fit into the rudder gudgeons. At the top end I made a socket to accept the cut off stainless steel mast support, and held it in place with epoxy and fiberglass scraps. Now I had a two height aft mast support: in the lower position for trailering, and with the stainless steel support placed into the wooden support, the aft end of the mast is high enough so that I can easily put the mast bolt in place (and the mast clears the forward edge of the companionway hatch in it's closed position) Then I can raise the mast easily; or lower it just as easily. The trick here is to have the aft end of the mast high enough so that it easily fits into the mast bracket and clears the hatch edge. .............oh, and a further reminder when raising your mast: Make sure that all your halyards; topping lift line; all run clear, or else you will have the mast raised and then will have to lower it again to untangle the mess. Been there! Done that too! Connie M15 #400