Pineapple Upside Down Rum Cake Recipe

Preheat oven to 350°F (175°C). Place a 9-inch round cake pan (preferably 2-3 inches deep or a bundt pan) on a wire rack. Melt 6 tablespoons butter in a small saucepan over medium heat until foamy.

Add 3 tablespoons dark brown sugar and 3 tablespoons light brown sugar to the melted butter. Stir constantly and cook 2–3 minutes until sugar dissolves and mixture is syrupy but not overly dark.

Remove pan from heat briefly and stir in 2 tablespoons dark rum. Return to low heat 20–30 seconds to blend and reduce slightly; be cautious if rum is flammable. Pour the warm caramel evenly into the prepared cake pan, tilting to coat the bottom.

Arrange pineapple rings in a single layer over the caramel. Place a halved cherry in the center of each ring and additional cherries in the gaps to create an even decorative layer. Set pan aside while you make the batter.

In a medium bowl whisk together 1.75 cups all-purpose flour, 2 teaspoons baking powder, and 1/2 teaspoon salt. Set aside.

In the bowl of a stand mixer fitted with the paddle (or in a large bowl with a hand mixer), beat 8 tablespoons softened unsalted butter and 1 cup granulated sugar on medium-high speed until light, pale and fluffy, about 3–4 minutes.

Add the eggs one at a time, beating well after each addition and scraping down the bowl so mixture stays homogeneous.

Mix in 2 teaspoons vanilla extract and 2 tablespoons light rum until incorporated.

With the mixer on low, add about one-third of the dry ingredients, then half of 3/4 cup whole milk, then another third of the dry ingredients, the remaining milk, and the final third of dry ingredients. Mix just until combined—do not overmix.

Scrape batter over the arranged pineapples and cherries in the pan, smoothing the top with a spatula. The batter should reach near the top but not overflow; if using a 9x13, increase batter accordingly.

Bake in the preheated 350°F (175°C) oven for 35–45 minutes, or until a toothpick inserted into the center comes out with a few moist crumbs and the top is golden. Baking time may vary with pan type; check at 30 minutes if using a shallow pan.

When done, remove cake from oven and let cool in pan on a wire rack for 10 minutes. Run a thin knife around the pan sides to loosen the cake. Place a serving plate over the pan and invert quickly but carefully. Tap the bottom of the pan to release the cake; lift pan off. If any pineapple sticks, gently loosen and reposition.

While the cake finishes cooling (or after it is inverted), make the glaze. In a small saucepan combine 1/2 cup dark brown sugar and 2 tablespoons butter over medium heat. Stir until the sugar dissolves and the butter melts.

Carefully stir in 1/4 cup heavy cream and bring just to a simmer; simmer 1–2 minutes until slightly thickened. Remove from heat and stir in 2 tablespoons dark rum and a pinch of salt. Taste and adjust salt or rum to preference.

Drizzle warm glaze over the inverted cake, letting it pool slightly around the bananas and drip down the sides. (Note: glaze can be reheated briefly if it thickens.)

Serve slices warm or at room temperature. Store leftovers covered in the refrigerator up to 3 days; bring to room temperature or warm gently before serving.