Pineapple Upside Down Cake Recipe

Prepare pan and caramel

Preheat oven to 350°F (175°C). Place a 9-inch round cake pan (or 9x2-inch) on the counter. In a small saucepan over medium heat, melt 4 tbs unsalted butter. Add 1 cup packed light brown sugar and stir until sugar dissolves and mixture is smooth and bubbling, about 2–3 minutes. Pour the hot caramel evenly into the bottom of the prepared cake pan and spread to cover.

Arrange pineapple and cherries

While caramel is warm, arrange 8 pineapple rings in a single layer over the caramel. Place 1 maraschino cherry in the center of each pineapple ring. If using fresh pineapple, pat rings dry so they don’t slide.

Preheat and measure

Reduce oven temperature if needed to maintain 350°F. Measure and have ingredients at room temperature (butter, eggs, milk) for best texture.

Combine dry ingredients

In a medium bowl, whisk together 1.5 cups all-purpose flour, 1 tsp baking powder, 0.5 tsp salt, and 3 tbs granulated sugar until evenly blended.

Cream butter and sugar

In a large mixing bowl, cream 6 tbs softened unsalted butter with remaining granulated sugar (3 tbs) until light and fluffy, about 2–3 minutes with an electric mixer on medium speed. Scrape down the bowl as needed.

Add eggs and vanilla

Beat in 2 large eggs, one at a time, mixing well after each addition. Add 1 tsp vanilla extract and mix until incorporated.

Alternate dry and wet

With the mixer on low speed, add the dry flour mixture in three additions, alternating with 1/2 cup whole milk: start and end with the dry ingredients (dry–milk–dry–milk–dry). Mix each addition just until combined; do not overmix.

Pour and smooth

Carefully spoon or pour the batter over the arranged pineapple rings in the pan, spreading gently to cover the fruit evenly. The batter will be thick; use an offset spatula to smooth the top and fill gaps between rings.

Bake

Bake in preheated 350°F (175°C) oven for 30–38 minutes, until the cake is golden on top and a toothpick inserted into the center comes out clean or with a few moist crumbs.

Cool slightly

Remove the pan from the oven and set it on a wire rack. Let the cake cool in the pan for 10–12 minutes—long enough for the caramel to set slightly but while still warm for easy unmolding.

Invert onto serving plate

Run a thin knife around the edge of the cake to loosen. Place a heatproof serving plate over the pan and, using oven mitts, invert the pan and plate together. Lift the pan off carefully—if any pineapple sticks to the pan, lift it and place it back on the cake. If some caramel pools on the pan, spoon it over the cake.

Final cooling

Let the inverted cake cool for another 15–20 minutes before slicing so the caramel sets but cake is still warm. Serve warm or at room temperature.

If you want a shinier extra glaze, melt 1 tbs butter with 1 tbs extra brown sugar in a small skillet over low heat until sugar dissolves. Brush lightly over the pineapple rings after inversion.