Pineapple Upside Cake Recipe

Prepare pan and caramel

Preheat oven to 350°F (175°C). Place a 9-inch round cake pan on the stove over low heat. Add 1 tablespoon unsalted butter and let it melt, swirling to coat the pan. Add 1 cup light brown sugar and stir constantly until it dissolves and becomes a glossy caramel, about 2–3 minutes. Immediately remove from heat.

Arrange fruit

Quickly and carefully spread the caramel in an even layer across the bottom of the pan. Arrange 8 pineapple slices in a single layer over the caramel. Place a maraschino cherry in the center of each pineapple slice and, if desired, use smaller pieces of pineapple to fill gaps so the bottom is mostly covered.

Mix dry ingredients

In a medium bowl whisk together 1.5 cups all-purpose flour, 2 teaspoons baking powder, and 1/4 teaspoon salt until evenly combined.

Cream butter and sugar

In a large mixing bowl, beat 1/2 cup softened unsalted butter with 1 cup granulated sugar until light and fluffy, about 3–4 minutes. Scrape down the bowl as needed.

Add eggs and vanilla

Add 2 large eggs one at a time, beating briefly after each addition until incorporated. Mix in 1 teaspoon vanilla extract.

Combine batter

Alternately add the dry ingredients and 1/2 cup whole milk to the butter mixture in three additions, beginning and ending with the dry ingredients (dry–milk–dry–milk–dry). Mix each addition just until combined and no streaks of flour remain; do not overmix.

Pour and smooth

Spoon the batter evenly over the arranged pineapple and cherries in the prepared pan and smooth the top with a spatula. The batter will be thick but spreadable.

Bake

Bake in the preheated 350°F (175°C) oven until a toothpick inserted into the center comes out clean and the top is golden, about 35–40 minutes. If the top browns too quickly, loosely tent with foil for the last 10 minutes.

Cool slightly

Remove the pan from the oven and let it cool on a wire rack for 10–15 minutes. Cooling too long will make the caramel stick; this short rest lets the cake set so it will release cleanly.

Invert cake

Run a thin spatula or knife around the pan edges to loosen. Place a heatproof serving plate over the pan and, using oven mitts, invert the pan and plate together so the cake drops onto the plate with the caramelized pineapple on top. If any pineapple sticks to the pan, gently lift it onto the cake.

If desired, dust the cooled top lightly with 1 teaspoon powdered sugar before serving. Serve warm or at room temperature, sliced into 8 pieces.