Preheat your oven to 350°F. Generously spray a 10-inch iron skillet with cooking spray. Add 4 tablespoons of salted butter to the skillet and place it in the preheating oven just until the butter is melted. Once melted, carefully remove the skillet from the oven. Sprinkle the brown sugar evenly over the melted butter, then neatly arrange the drained pineapple slices on top. Set the skillet aside while you prepare the cake batter. I always make sure to slightly overlap the pineapple slices for a beautiful pattern once the cake is inverted.

In a medium bowl, whisk together the all-purpose flour, baking powder, and salt until well combined. Set aside; you'll add the wet mixture to this bowl in the next step.

In a separate large bowl, use a hand or stand mixer to cream together the softened salted butter and granulated sugar until fluffy and light in color. Beat in the eggs one at a time, ensuring each is thoroughly combined. Add the evaporated milk, vanilla extract, and 1/2 cup reserved pineapple juice and mix until smooth.

Add the wet mixture from Step 3 to the dry mixture from Step 2. Mix just until all the ingredients are fully incorporated and the batter is smooth. Avoid overmixing, as this can make the cake dense. I like to fold the batter gently with a spatula for a tender crumb.

Carefully spread the cake batter from Step 4 evenly over the arranged pineapple and brown sugar mixture in the skillet from Step 1. Smooth the surface. Bake in the preheated 350°F oven on the middle rack for 35 to 45 minutes, or until a toothpick inserted into the center comes out clean. If the top seems to be browning too quickly, you can tent it with foil.

Once baked, remove the skillet from the oven and allow the cake to cool for 10 to 15 minutes. Run a knife around the edges if needed, then place a plate or platter over the skillet and carefully invert the cake so the pineapple is on top. Decorate the top with maraschino cherries. For a beautiful presentation, I like to put a cherry in the center of each pineapple ring.