This Pineapple Upside-Down Cake is a classic dessert that brings tropical sweetness to your table. With caramelized pineapple slices and cherries on top of a soft, buttery cake, every bite is a delightful mix of rich flavors and textures. The cake is baked with the fruit at the bottom of the pan and flipped after baking, giving it a beautiful golden glaze. It’s perfect for special occasions or a casual treat, and surprisingly easy to make from scratch.
Preheat the Oven. Preheat your oven to 350°F (175°C). Grease a 9-inch round cake pan.
Prepare the Topping. Melt the 1/4 cup of butter in a small saucepan over medium heat. Stir in the brown sugar until dissolved and bubbly. Pour this mixture into the bottom of the prepared cake pan. Arrange the pineapple rings over the sugar mixture, placing a cherry in the center of each ring if desired.
Mix the Dry Ingredients. In a medium bowl, whisk together the flour, baking powder, baking soda, and salt. Set aside.
Cream Butter and Sugar. In a large mixing bowl, beat the softened butter and granulated sugar together until light and fluffy, about 2-3 minutes. Add the eggs one at a time, beating well after each addition. Mix in the vanilla extract.
Combine Wet and Dry. Gradually add the dry ingredients to the butter mixture, alternating with the milk and pineapple juice. Begin and end with the flour mixture, mixing until just combined.
Pour the Batter. Gently spoon the cake batter over the pineapple rings in the pan, spreading it evenly with a spatula.
Bake in the preheated oven for 40-45 minutes, or until a toothpick inserted into the center of the cake comes out clean. Allow the cake to cool in the pan for 10 minutes.
Invert the Cake. Run a knife around the edge of the pan to loosen the cake. Place a serving plate over the top of the pan and carefully flip the cake onto the plate. Let the cake cool for an additional 10 minutes before serving.
For an extra burst of pineapple flavor, you can add 1/2 cup of crushed pineapple into the cake batter. If you want a tangy twist, substitute whole milk with buttermilk for a richer, moist texture. Ensure the butter and sugar are well creamed to prevent the cake from sinking in the middle.