Pineapple Upside-down Cake Recipe

Prepare pan and caramel

Preheat the oven to 350°F (175°C). Place a 9-inch round cake pan on the stove over low heat. Add 4 tablespoons unsalted butter to the pan and let it melt. Stir in 1 cup light brown sugar and cook, stirring, until the sugar dissolves and the mixture is smooth and bubbling lightly, about 1–2 minutes. Remove from heat.

Arrange fruit

Carefully pour or spread the warm caramel evenly across the bottom of the prepared 9-inch pan. Arrange 8 pineapple rings on top of the caramel in a single layer, fitting them snugly. Place 1 maraschino cherry in the center of each pineapple ring. Set the pan aside to cool slightly while you make the batter. Reserve about 1/4 cup of pineapple juice from the canned rings for the batter.

Preheat and prepare

With the oven already at 350°F (175°C), ensure oven rack is in the center. In a medium bowl whisk together 1 1/2 cups all-purpose flour, 1 teaspoon baking powder, and 1/4 teaspoon salt. Set dry mix aside.

Cream butter and sugar

In a large bowl using a hand mixer or stand mixer fitted with the paddle, cream 6 tablespoons softened unsalted butter and 3/4 cup granulated sugar on medium speed until pale and fluffy, about 2–3 minutes.

Add eggs and flavor

Beat in 2 large eggs one at a time, mixing well after each addition. Scrape down the bowl. Mix in 1 teaspoon vanilla extract.

Combine wet and dry

With the mixer on low, add one-third of the dry ingredients and mix until just combined. Add half of the milk (1/4 cup) plus half of the reserved pineapple juice (about 2 tablespoons), then another third of the dry mix. Continue alternating and finish with the remaining dry ingredients, mixing only until just combined. Do not overmix.

Assemble and bake

Spoon the batter evenly over the arranged pineapple rings and caramel in the pan, spreading gently to fill gaps. Smooth the top lightly. Bake in the preheated oven for 30–35 minutes, or until a toothpick inserted into the center of the cake (avoiding pineapple) comes out clean or with only moist crumbs.

Cool and invert

Remove the cake from the oven and let it cool in the pan on a wire rack for 10–12 minutes (do not cool completely, or the caramel will harden and stick). Run a knife around the edge to loosen if needed. Place a serving plate larger than the pan upside down over the cake pan, then carefully invert the pan and plate together. Lift the pan off slowly to reveal the pineapple-topped cake. If any pineapple rings stick to the pan, gently re-arrange them on the cake.

Finish

Let the cake cool on the serving plate for another 10–15 minutes to allow the caramel to set slightly. Serve warm or at room temperature; slice into 8 pieces. Leftovers can be stored covered at room temperature for 1 day or refrigerated up to 3 days. Reheat slices briefly in the microwave before serving if desired.