For the pineapple cake: Preheat the oven to 350 degrees F. Line two 9-inch cake pans with parchment and spray the sides with cooking spray.
In a mixer, blend the granulated sugar and shortening, then add the milk, cherries, whole egg and egg white and mix to combine. In a bowl, combine the flour, baking powder and salt. Slowly add the dry ingredients to the mixer and mix until smooth.
Lay down 4 pineapple slices in each pan and fill three-quarters of the way with the batter. Bake until golden brown, about 35 minutes. Let cool slightly, then remove the cakes from the pans to a wire rack to cool completely.
For the strawberry filling: In a mixer, beat the cream cheese and butter until fully incorporated. Mix in the vanilla. Slowly beat in the confectioners' sugar until smooth and fluffy. Fold in the strawberry preserves.
Spread the strawberry filling in between the 2 layers of cake. Smear a very thin coating of the strawberry filling around the sides and top of the stacked cake.
This recipe was created by a contestant during a cooking competition. It has not been tested for home use.