Place 1/4 cup butter in a 9-inch square pan and then place the pan into the oven to melt.
When melted, sprinkle 2/3 cup brown sugar evenly in the pan and then pack the sugar down slightly.
Arrange 9 pineapple slices in the pan in rows of three.
Place 9 cherries in the center of each pineapple slice.
Then, in a KitchenAid mixing bowl, beat all of the remaining ingredients for three minutes which includes the flour, shortening, salt, white sugar, baking powder, milk and 1 egg.
Carefully pour the cake batter over the pineapples and then spread it evenly with a spatula.
Finally, bake the Pineapple Upside Down Cake for 50-55 minutes.
When the cake pan is removed from the oven, immediately place the heated pan on a platter, then carefully flip the pan onto the platter. Then, remove the pan from off of the cake.