Using a spoon, scoop a ¾ cup of the undrained crushed pineapple into a small bowl and set aside. Drain the remaining pineapple, reserving 1 cup of drained crushed pineapple and the juice; set aside.
Cream shortening, butter, and sugar together in a mixing bowl until smooth. Add eggs, one at a time, beating thoroughly after each addition. In a small bowl, sift the flour and baking powder together. Alternate the dry and wet mixtures to the creamed mixture, one at a time. Add some of the flour and baking powder to the creamed mixture, incorporated, then add some milk. When both the flour mixture and the milk are combined, add vanilla and stir in ¾ cup of the undrained pineapple to the batter and blend well. Pour the batter into a well-greased and floured bundt pan. Place the bundt pan into a cold oven, then turn on the oven; set the temperature to 325 degrees F. Bake for 1 hour 30 minutes, or until a toothpick comes out clean when inserted into the cake.
Cool the cake for 10 to15 minutes in the pan, then run a knife around edges to loosen and remove cake carefully to a rack, while making the glaze.
In a small bowl, combine butter, sugar, and 1 cup drained pineapple. If the mixture is too dry add some of the reserved juice a little at the time to loosen up the sugar mixture enough to make a sauce. Pour pineapple sauce over cake while still hot.
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