Preheat oven to 350 degrees. Gather your ingredients so that you have everything close at hand on the counter or table.
Make the Topping
In a large cast iron skillet, melt butter. Add brown sugar and stir until combined.
Arrange pineapple slices and cherries on top of sugar mixture. Sprinkle with pecans. Set aside.
Prepare the Cake
In large mixing bowl, cream together the granulated sugar, vegetable shortening, and softened butter. Add in large eggs and vanilla extract to combine.
In a small bowl, combine the cake flour, baking powder, and salt.
Add to creamed mixture alternately with whole milk.
Pour batter over the arranged pineapple slices. Bake in preheated oven for 40-45 minutes until cake tests done with a toothpick in the center.
Allow to cool for 10 minutes. Scrape sides of pan with knife, then, invert cake onto a serving plate. Serves 8-10
Notes
*Unless otherwise indicated, all butter on this recipe site is salted.