Preheat oven to 350℉. 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 1/3 cup butter. Add 3/4 cup brown sugar and stir until combined.
Arrange 20 oz. pineapple ring slices and 18 whole Maraschino cherries on top of sugar mixture. Sprinkle with 1/2 cup pecan halves. Set aside.
For best practice, be sure to arrange the pineapple and cherries before the pecans to ensure a visibly nice top after turning.
Prepare the Cake Batter
In large mixing bowl, cream together 3/4 cup granulated sugar, 1/4 cup vegetable shortening, and 1/4 cup butter. Add in 1/4 cup reserved pineapple juice, 2 large eggs, and 2 teaspoons vanilla extract to combine.
In a small bowl, combine 2 cups cake flour, 1 tablespoon baking powder, and 1 teaspoon salt.
Add to creamed mixture alternately with 3/4 cup 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 2-3 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.