2 1/2 cups all purpose flour
1 tbsp baking powder
1 tsp salt
2 cups granulated sugar
1 stick unsalted butter, at room temperature
1/4 cup vegetable shortening
1 1/2 cups whole milk
2 large eggs
2 tsp vanilla extract
1 20 oz can sliced pineapple, + 2 tbsp juice
1 1/3 cups packed light brown sugar
Maraschino cherries, stemmed
Preheat oven to 350F. Mix together flour, baking powder, salt, granulated sugar, 1/2 stick butter, shortening, milk, eggs, vanilla, and 2 tbsp juice. Mix until well combined and smooth, its ok is there are a few small lumps.
Melt the other half of the stick of butter in a 12 inch cast iron skillet on medium heat, swirl to coat the bottom. Sprinkle brown sugar over butter and evenly distribute, making sure the entire surface is covered in brown sugar. Do not stir the mixture. As soon as it dissolves, remove from heat and line with pineapple. Add cherries to centers of pineapple.
Pour batter over pineapple slices evenly and gently spread over top. Bake for about 30-40 minutes, or until a toothpick inserted comes out clean.
Run a knife around the edge of the cake and place upside down on a plate bigger than the pan.