1-First step: Preheat and prepare the pan Start by preheating your oven to 350°F. Use a 9.5- to 10-inch pie plate for this recipe, since it gives the cake enough room to bake evenly and flip cleanly later. Melt the 1/4 cup salted butter in the pie plate, then spread it over the bottom and sides so the fruit topping has a rich, buttery base. Once the butter is in place, sprinkle the 1/2 cup packed brown sugar evenly over the bottom of the pan. This layer turns into the glossy topping that makes a Classic Pineapple Upside Down Cake Recipe so memorable. Take a moment to spread the sugar to the edges for even caramelization.

2-Second step: Arrange the fruit Place the 10 patted-dry pineapple slices in a single layer over the brown sugar. Patting the slices dry matters because extra juice can make the cake watery. Add maraschino cherries in the centers of the pineapple rings and around the edges of the pan for a pretty finish.

3-Third step: Make the cake batter In a mixing bowl, beat the 1/2 cup softened unsalted butter and 3/4 cup granulated sugar until the mixture looks creamy and light. Add the 2 large room-temperature eggs one at a time, mixing after each one. Then stir in the 1 teaspoon vanilla extract. In a separate bowl, whisk together the 1 and 1/2 cups all-purpose flour, 1 and 1/2 teaspoons baking powder, and 1/4 teaspoon salt. This helps the leavening spread evenly through the batter. Add the dry ingredients and the 1/2 cup room-temperature whole milk to the butter mixture a little at a time, alternating between them and stirring only until combined. Do not overmix, or the cake can turn dense instead of soft.

4-Fourth step: Pour and bake Carefully spoon or pour the batter over the fruit layer in the pie plate. Spread it gently to the edges so the topping stays covered. Place the cake in the oven and bake for 30 minutes. After 30 minutes, loosely cover the cake with foil if it is browning too quickly. Then bake for another 15 minutes, or until a toothpick inserted in the center comes out mostly clean. The full bake time is usually 45 minutes, but ovens can vary, so begin checking near the end of the baking window.

5-Fifth step: Cool and invert When the cake is done, let it cool for 10 to 15 minutes before flipping. This cooling time helps the caramel set up a little, which makes the cake easier to release. If needed, run a thin knife around the edges to loosen the cake from the pan. Place a serving platter over the pie plate, then invert the cake in one steady motion. Lift the pan away slowly so the pineapple topping stays in place. If a cherry or pineapple slice sticks, nudge it back into position with a spoon or spatula. Serve warm for the best texture and flavor.