1-First Step: Prepare the oven and pan Preheat your oven to 350°F. Use a 9.5 to 10 inch pie plate for the best results. Pour the ¼ cup melted salted butter into the pan and spread it evenly up the sides. This buttery layer helps the topping caramelize and makes the cake easier to remove later.

2-Second Step: Build the fruit topping Sprinkle the ½ cup packed brown sugar evenly over the buttered bottom of the pan. Next, arrange the 10 pineapple slices over the sugar. Place maraschino cherries in the centers and around the fruit as desired. Be sure to pat the pineapple slices dry first so the topping does not get watery.

3-Third Step: Cream the butter and sugar In a large bowl, beat the ½ cup softened unsalted butter with the ¾ cup granulated sugar until creamy and smooth. This step adds air to the batter and helps the cake bake up light. Add the 2 large eggs one at a time, mixing after each addition. Stir in the 1 teaspoon vanilla extract.

4-Fourth Step: Mix the dry ingredients In a separate bowl, whisk together the 1 ½ cups all-purpose flour, 1 ½ teaspoons baking powder, and ¼ teaspoon salt. Mixing the dry ingredients first helps the cake rise evenly. If you are using gluten-free flour, this is the moment to swap it in.

5-Fifth Step: Combine wet and dry ingredients Add the dry mixture to the butter mixture in alternating additions with the ½ cup whole milk. Start with a little flour, then a little milk, and repeat until everything is just combined. Stop mixing as soon as the batter comes together. Over-mixing can make the cake dense instead of soft.

6-Sixth Step: Pour and bake Carefully pour the batter over the pineapple topping and spread it gently to the edges. Bake for 30 minutes first. Then loosely cover the cake with foil and bake for another 15 minutes. The foil helps prevent over-browning while the center finishes baking.

7-Seventh Step: Check for doneness Insert a toothpick into the center of the cake. It should come out with a few crumbs, not wet batter. If the top is browning too fast, keep the foil in place. If you are using a cast iron skillet instead of a pie plate, begin checking a little earlier because cast iron can bake faster.

8-Eighth Step: Cool and invert Let the cake cool for 10 to 15 minutes after baking. This resting time helps the fruit layer settle so it releases cleanly. Run a knife gently around the edges if needed. Place a serving platter over the pan, hold both firmly with oven mitts, and flip in one confident motion. Lift the pan slowly so the pineapple topping stays in place.

9-Ninth Step: Serve and enjoy Serve the cake warm for the best texture and flavor. The caramel topping is glossy, the fruit is juicy, and the vanilla cake stays soft underneath. This dessert is especially good fresh from the oven, though leftovers still taste great later in the day.