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I had to add quite a bit more flour to have a workable dough, and had quite a bit of pineapple mixture left over, but the end product was very good! While it bakes, the dough absorbes some of the pineapple mixture and makes it nice and moist. So, you don't have to worry about making a super tight seal around the edges.
Thanks for posting this recipe. My mother's recipe was lost years ago and of course none of us had her recipes. We use other fillings also ie: blueberry, cherry and sometimes peach. Instead of powdered sugar my mother used what some people call "Crisco" icing.