1-First Step: Prepare the pan and oven Start by preheating your oven to 350°F. Grease a 9-inch round cake pan or a 9 to 10-inch cast iron skillet, depending on the look you want. A cast iron skillet gives the pineapple upside down cake a rustic finish and browns the bottom beautifully. If you are using a skillet, set it over low heat for a minute or two so the butter melts smoothly. Pour the 1/4 cup salted butter, melted into the pan and spread it evenly. Sprinkle the 1/2 cup tightly packed brown sugar over the butter so the topping forms a sweet caramel base. This is the layer that turns the cake into a true classic pineapple upside down cake.

2-Second Step: Arrange the fruit topping Place the 10 pineapple slices, patted dry over the brown sugar mixture. Arrange them in a single layer so the whole top is covered. Add a maraschino cherry in the center of each pineapple ring or tuck cherries into any open spaces around the edges. This makes the finished pineapple cake look polished and old-fashioned. Drying the pineapple is a small step, but it helps a lot. It keeps the topping from becoming watery and gives you better caramelization. If you want a deeper flavor, you can gently press the fruit into the sugar layer so it sits snugly in the pan.

3-Third Step: Make the vanilla cake batter In a large mixing bowl, beat the 1/2 cup unsalted butter, softened to room temperature with the 3/4 cup granulated sugar until the mixture looks light and fluffy. This usually takes about 2 to 3 minutes with a hand mixer. Next, add the 2 large eggs, at room temperature, one at a time, mixing well after each addition. Stir in the 1 teaspoon vanilla extract. In a separate bowl, whisk together the 1 1/2 cups all-purpose flour, 1 1/2 teaspoons baking powder, and 1/4 teaspoon salt. Add the dry ingredients to the butter mixture in two parts, alternating with the 1/2 cup whole milk, at room temperature. Start and end with the flour mixture. Mix just until combined. Overmixing can make the cake tough instead of soft.

4-Fourth Step: Spread the batter over the fruit Spoon the batter carefully over the pineapple layer. Use a spatula to spread it gently all the way to the edges without disturbing the fruit. The batter may look thick, and that is normal. Try to cover the pineapple evenly so the cake bakes into a level layer. If you are making this easy pineapple upside down cake for a crowd, you can double the recipe and bake it in two pans. For a smaller household, this single cake is just right and still feels special.

5-Fifth Step: Bake until golden Bake the cake for 30 to 40 minutes at 350°F. If you are using a cast iron skillet, start checking around 30 to 35 minutes since cast iron holds heat well. The cake is ready when the top is golden and a toothpick inserted into the center comes out clean or with just a few moist crumbs. For a more detailed look at baking styles and recipe comparisons, you can also read this pineapple upside down cake bake-off review.

6-Final Step: Flip and serve Let the cake rest in the pan for 10 to 15 minutes. This short cooling time helps the topping settle so the cake releases cleanly. Run a thin knife around the edges to loosen any spots where the cake meets the pan. Place a serving plate over the pan, hold both together firmly, and flip in one quick motion. If any pineapple slices stick, gently lift them with a spatula and place them back on top. Serve the cake warm for the best texture. It is wonderful on its own, but a spoonful of whipped cream or vanilla ice cream makes each slice feel extra special.