1-First Step: Preheat and prepare the pan Preheat your oven to 350°F. Pour the 1/4 cup melted salted butter into a 9.5 to 10-inch pie plate, then spread it around the bottom and sides of the dish. Sprinkle the 1/2 cup packed brown sugar evenly over the butter so it forms a sweet base. This step is what gives the cake its classic glossy top and helps keep the fruit in place.

2-Second Step: Arrange the fruit Lay the 10 pineapple slices in the pan and pat them dry first so extra juice does not pool in the topping. Add the maraschino cherries in the centers and around the fruit as desired. This is also the time to make the cake look pretty, so place the rings in a neat pattern. If you like a rustic look, slightly overlapping the slices works just fine.

3-Third Step: Make the cake batter In a large bowl, beat the 1/2 cup softened unsalted butter and 3/4 cup granulated sugar until creamy. This usually takes about 2 to 3 minutes with a hand mixer. Add the 2 large eggs one at a time, mixing after each egg. Stir in the 1 teaspoon vanilla extract. This is what gives your pineapple upside down cake recipe its warm, classic cake flavor.

4-Fourth Step: Mix the dry ingredients In another bowl, whisk together the 1 1/2 cups all-purpose flour, 1 1/2 teaspoons baking powder, and 1/4 teaspoon salt. Whisking helps distribute the baking powder evenly, which means the cake bakes up with a more even rise. If you are baking gluten-free, use a 1:1 baking blend and mix just until combined so the cake stays soft.

5-Fifth Step: Combine wet and dry ingredients Alternate adding the dry mixture and the 1/2 cup whole milk into the butter mixture, starting and ending with the dry ingredients. Mix gently after each addition until the batter is just combined. Do not over-mix, or the cake can become dense instead of tender. If you want to use pineapple juice instead of milk, that is a simple swap that can add a little extra fruit flavor.

6-Sixth Step: Pour and bake Carefully spoon the batter over the pineapple layer and spread it out evenly. Bake for 30 minutes, then loosely cover the pan with foil and bake for another 15 minutes. The foil helps keep the top from browning too fast while the center finishes baking. Start checking with a toothpick at the 30-minute mark, especially if you are using a cast iron skillet, since it may bake faster.

7-Seventh Step: Cool and flip Once the cake looks mostly set and a toothpick comes out mostly clean, remove it from the oven. Cool it in the pan for 10 to 15 minutes. This cooling time helps the topping settle so the cake releases cleanly. Run a knife around the edges if needed, place a serving platter over the pan, and invert with confidence. Lift the pan away slowly and let the topping settle into place.

8-Eighth Step: Slice and serve Serve the cake warm or at room temperature. Each slice should show a golden pineapple top, tender vanilla crumb, and a caramelized finish that feels homey and special. This recipe makes 8 servings, which is perfect for a family dessert or a small gathering. If you want another pretty fruit dessert for your table, take a look at my peach cobbler recipe.