Pineapple Upside Down Cake Recipe

Prepare pan and caramelize sugar

Preheat oven to 350°F (175°C). In a 9-inch round cake pan, melt 4 tbs unsalted butter over low heat (or melt in a small saucepan). Stir in 3 tbs packed light brown sugar until dissolved and bubbling. Spread the caramel evenly across the bottom of the pan.

Arrange pineapple and cherries

Place 6 pineapple rings on top of the caramel in a single layer. Put a maraschino cherry in the center hole of each ring. Sprinkle the 1 cup candied pecans evenly over and between the pineapple rings. Set pan aside while you make the batter.

Make candied pecans first so they can cool. Line a baking sheet with parchment. In a small skillet over medium heat, combine 1 cup pecan halves, 2 tbs granulated sugar, 1 tsp unsalted butter, and 1/8 tsp salt. Stir constantly until the sugar melts and coats the pecans, about 3–5 minutes. Spread nuts on the parchment to cool and separate any clumps with a fork. Reserve 1 cup for topping; any extra can be stored for another use.

Make the sauce while cake bakes or ahead. In a medium heavy-bottomed saucepan over medium heat, add 3/4 cup granulated sugar. Without stirring initially, let sugar melt at the edges; gently swirl the pan occasionally until fully amber in color, about 6–8 minutes. Remove from heat and carefully whisk in 4 tbs unsalted butter until incorporated. Slowly pour in 1/2 cup heavy cream (mixture will bubble vigorously) and whisk until smooth. Stir in 1/8 tsp salt and 1/2 tsp vanilla. If there are any small lumps, return to very low heat and whisk until smooth. Set aside to cool slightly. Reserve 1 cup for serving with the cake; leftover sauce keeps refrigerated up to 1 week.

Cream butter and sugar: In a large mixing bowl, beat 8 tbs (1 stick) softened unsalted butter and 1 cup granulated sugar with a hand or stand mixer on medium speed until pale and fluffy, about 3–4 minutes.

Add eggs and flavor: Add 2 large eggs one at a time, beating well after each addition. Mix in 2 tbs light rum and 1 tsp vanilla extract until combined.

Combine dry ingredients: In a separate bowl, whisk together 1 3/4 cups all-purpose flour, 2 tsp baking powder, and 1/2 tsp salt.

Alternately add dry and milk: With mixer on low, add one-third of dry ingredients, then half of 1/2 cup whole milk; repeat, ending with dry ingredients. Scrape bowl and mix just until combined — do not overmix.

Assemble in pan: Spoon batter over the arranged pineapple in the prepared pan, spreading gently and evenly. The batter will be thick; fill so it comes nearly to the top but leaves room for rise (about 3/4 full). Smooth the top.

Bake: Bake in the preheated 350°F (175°C) oven for 35–45 minutes, or until a toothpick inserted in the center comes out with a few moist crumbs and the top is golden. If edges bubble too aggressively, tent loosely with foil for last 10 minutes.

Cool and invert: Remove cake from oven and allow to cool in pan on a wire rack for 10–15 minutes — not completely cool, or caramel will stick. Run a thin knife around pan edge to release. Place a serving plate over the pan and carefully invert cake, tapping the bottom of the pan to release. If any pineapple or nuts stick to the pan, lift them out and arrange back on the cake. Spoon any caramel puddled in the pan over the top.

Warm sauce and plate: If caramel sauce has chilled, warm gently in microwave (10–15 seconds) or in a small saucepan until pourable. Slice the cake into 8 wedges. Place a wedge on each plate, drizzle 1–2 tbs warm caramel sauce over it, scatter additional candied pecans on top, and serve with a scoop of vanilla gelato (approximately 1 scoop per serving).