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Pineapple Upside Down Cake Recipe

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3.8 from 26 reviews

This classic Pineapple Upside Down Cake features a caramelized butter and brown sugar topping, layered with juicy pineapple rings and maraschino cherries, baked to moist perfection with a tender, fluffy cake base infused with almond extract. Perfect for dessert or a special occasion, this recipe yields 12 delicious servings in under an hour.

  • Total Time: 55 minutes
  • Yield: 12 servings

Ingredients

Caramel and Fruit Topping

  • ½ cup (4 oz/115 g) butter
  • 1 ¼ cups (7½ oz/213 g) dark brown sugar
  • 2 cans (20 oz/567 g) sliced pineapple in juice (12 slices)
  • 10-13 maraschino cherries (stems removed)

Cake Batter

  • 2 cups (10 oz/284 g) all-purpose flour
  • 2 teaspoons baking powder
  • ½ teaspoon salt
  • ½ cup (4 oz/115 g) butter, softened
  • ½ cup (4 oz/115 g) granulated sugar
  • ⅓ cup (2 oz/57 g) dark brown sugar
  • 2 large eggs, at room temperature
  • ½ cup (4 fl oz/120 ml) whole milk
  • ½ cup (4 fl oz/120 ml) juice from the tinned pineapple
  • 1 teaspoon almond extract

Instructions

  1. Prepare the baking pan: Preheat your oven to 350°F (180°C). Generously butter a 9×13-inch (23×33 cm) baking pan to prevent sticking and set it aside for later.
  2. Make the caramel: In a small saucepan over medium-low heat, combine ½ cup butter and 1 ¼ cups dark brown sugar. Simmer gently, stirring occasionally, until the sugar dissolves completely, about 2-3 minutes. Pour this caramel mixture evenly into the prepared baking pan.
  3. Arrange the fruit: Drain the pineapple rings, reserving ½ cup juice for the cake batter. Lay the pineapple slices in a single layer over the caramel in the baking pan, fitting approximately 4 x 3 slices. Place a maraschino cherry in the center of each pineapple ring.
  4. Mix dry ingredients: In a medium bowl, whisk together the flour, baking powder, and salt until well combined. Set this mixture aside.
  5. Cream butter and sugars: Using a stand mixer or electric hand mixer, beat the softened ½ cup butter with both the granulated sugar and ⅓ cup dark brown sugar on high speed until the mixture becomes light and fluffy, about 3 minutes.
  6. Add eggs: Beat in the eggs one at a time, making sure each is fully incorporated before adding the next.
  7. Combine dry and wet ingredients: Gradually add the dry ingredient mixture to the creamed butter and sugar, mixing until the mixture resembles coarse bread crumbs.
  8. Add liquids and flavoring: Slowly pour in the whole milk, reserved pineapple juice, and almond extract while mixing on low speed. Continue mixing until the batter is just combined and light in texture.
  9. Assemble and bake: Carefully spread the cake batter evenly over the arranged pineapples in the pan. Bake in the preheated oven for 35-40 minutes, or until a wooden skewer inserted into the center comes out clean.
  10. Cool and invert: Allow the cake to cool for 10 minutes in the pan. Then invert the cake onto a serving tray so the caramelized pineapple topping is on top.
  11. Serve and store: This cake is best enjoyed the day it is made. Cover and store any leftovers at room temperature for up to 2 days.

Notes

  • Use room temperature eggs for a better batter consistency.
  • Be careful when inverting the cake as the caramel topping will be hot and sticky.
  • Ensure the cake is fully cooled before slicing to maintain its structure.
  • The almond extract can be substituted with vanilla extract if desired.
  • For a lighter version, you can reduce the butter slightly but it may affect moistness.
  • Author: Olivia
  • Prep Time: 15 minutes
  • Cook Time: 40 minutes
  • Category: Dessert
  • Method: Baking
  • Cuisine: American