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Pineapple upside-down cake with golden caramelized rings, red cherries, and one slice showing the tender vanilla crumb.

Pineapple Upside-Down Cake with Golden Caramelized Pineapple

A classic 9-inch pineapple upside-down cake with glossy brown sugar caramel, seven pineapple rings, cherries, and a tender sour cream crumb that stays sturdy enough for a clean inversion.
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Prep Time 30 minutes
Cook Time 45 minutes
Cooling 1 hour 30 minutes
Total Time 2 hours 45 minutes
Servings: 10 slices
Course: Dessert
Cuisine: American
Calories: 376
Ingredients Equipment Method Notes

Ingredients
  

  • 56 g unsalted butter 1/4 cup, melted, for the caramel topping
  • 150 g light brown sugar 3/4 cup, firmly packed
  • 340 g canned pineapple rings in juice 7 rings, drained weight from one 20-ounce can; reserve the juice
  • 7 whole maraschino cherries drained, stems removed, and blotted dry
  • 200 g all-purpose flour 1 2/3 cups, spooned and leveled if not weighed
  • 6 g baking powder 1 1/2 teaspoons
  • 2 g baking soda 1/2 teaspoon
  • 3 g fine sea salt 1/2 teaspoon
  • 113 g unsalted butter 1/2 cup, softened to cool room temperature, for the cake
  • 150 g granulated sugar 3/4 cup
  • 100 g large eggs 2 eggs without shells, at room temperature
  • 5 g pure vanilla extract 1 teaspoon
  • 120 g full-fat sour cream 1/2 cup, at room temperature and stirred smooth
  • 80 g reserved pineapple juice 1/3 cup, measured after draining the pineapple

Equipment

  • 9-inch round light-colored metal cake pan with 2-inch sides
  • Large rimmed serving plate or cake stand
  • Digital kitchen scale
  • Stand mixer with paddle attachment or electric hand mixer
  • Two medium mixing bowls
  • fine mesh strainer
  • Silicone spatula
  • Pastry brush
  • Wire cooling rack
  • Thin offset spatula or table knife
  • Wooden skewer or cake tester

Method
 

  1. Set a rack in the center of the oven and heat it to 350°F. Lightly brush the sides of a solid 9-inch by 2-inch round metal pan with softened butter, leaving the bottom unlined. Drain the pineapple rings in a fine-mesh strainer for 15 minutes, reserving the juice. Arrange the rings and cherries on paper towels, then blot both sides thoroughly. Surface moisture can thin the caramel and leave a slippery, underbaked-looking band beneath the fruit.
  2. Pour the 56 grams melted butter into the prepared pan and tilt the pan until the bottom is evenly coated. Sprinkle the light brown sugar over the butter, breaking up firm lumps with your fingertips. Use a small offset spatula to spread the mixture into an even layer without stirring it into a paste. Level coverage matters because thick mounds produce syrupy pockets, while bare areas allow the pineapple to stick directly to the metal.
  3. Place one blotted pineapple ring in the center of the pan and arrange the remaining six evenly around it, pressing them lightly into the sugar without pushing the caramel aside. Set one dry cherry in the center of each ring. Keep the fruit in a single layer and leave small channels between the rings so the cake batter can reach the pan bottom and anchor the topping. Set the assembled pan aside while mixing the batter.
  4. Whisk the flour, baking powder, baking soda, and salt in a medium bowl for about 30 seconds. In a stand mixer fitted with the paddle, beat the softened 113 grams butter and granulated sugar on medium speed for 3 to 4 minutes, scraping the bowl halfway through. Stop when the mixture looks pale, fluffy, and slightly increased in volume. Proper creaming creates small air cells, but greasy or melted butter cannot hold them effectively.
  5. Beat in the eggs one at a time on medium-low speed, mixing for about 30 seconds after each and scraping the bowl before adding the next. Blend in the vanilla. Whisk the sour cream and 80 grams pineapple juice together until smooth. On low speed, add the flour mixture in three portions, alternating with the sour cream mixture in two portions. Stop when only a few flour streaks remain, then fold by hand until the batter is thick, smooth, and uniform.
  6. Spoon the batter gently over the arranged fruit in several mounds, then spread it to the edges with a silicone spatula without disturbing the rings. Smooth the surface and tap the pan once on a folded towel to settle large air pockets. Bake at 350°F for 42 to 48 minutes. The cake is done when the center springs back lightly, the edges pull just slightly from the pan, and a skewer inserted into the cake portion returns with moist crumbs but no wet batter.
  7. Transfer the pan to a wire rack and cool for exactly 10 minutes. Run a thin knife around the side without cutting beneath the cake. Center a large rimmed serving plate over the pan, hold both firmly with oven mitts, and invert them in one confident motion. Leave the pan in place for 30 seconds so the syrup drains onto the fruit, then lift it straight up. Replace any displaced fruit carefully and cool for at least 80 minutes before slicing with a serrated knife.

Notes

  • Use a solid, light-colored metal pan rather than a springform pan. Caramel can leak through a removable base, while very dark metal may brown the outer crumb before the center finishes baking.
  • Blot the pineapple until paper towels no longer become visibly wet. Draining alone removes packing juice, but it does not remove the film of moisture clinging to each ring.
  • Keep the topping level before arranging the fruit. Uneven brown sugar creates concentrated syrup pockets that can run down the cake or leave sections stuck to the pan.
  • Spread the thick batter by moving from the center toward the edge with light pressure. Dragging the spatula against the fruit can shift the carefully arranged rings and expose bare caramel.
  • Set a timer as soon as the cake leaves the oven. Turning it out immediately risks tearing the fragile crumb, while a long pan rest allows the caramel to cool, thicken, and glue the fruit to the bottom.