Pineapple Upside-Down Cake

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Classic Pineapple Upside-Down Cake is a timeless dessert featuring a soft, buttery vanilla cake baked over a golden, caramelized topping of sweet pineapple rings and vibrant maraschino cherries.

Ingredients

For the Caramelized Topping:

  • Unsalted butter: ¼ cup (½ stick), melted
  • Packed light or dark brown sugar: ½ cup
  • Canned pineapple slices in juice: 1 can (20 oz), drained (reserve 2 tablespoons of juice for the cake batter)
  • Maraschino cherries: 10 to 12 cherries (patted dry with a paper towel)
For the Cake Batter:

  • All-purpose flour: 1 ½ cups
  • Baking powder: 1 ½ teaspoons
  • Salt: ¼ teaspoon
  • Unsalted butter: ½ cup (1 stick), softened to room temperature
  • Granulated sugar: ¾ cup
  • Large eggs: 2, room temperature
  • Vanilla extract: 1 teaspoon
  • Whole milk: ⅓ cup, room temperature
  • Reserved pineapple juice: 2 tablespoons

Step-by-Step Instructions

1. Prepare the Pan and Topping

  1. Preheat your oven to 350°F (175°C).
  2. Pour the melted butter directly into an ungreased 9-inch round cake pan (or a 9-inch cast-iron skillet).
  3. Evenly sprinkle the brown sugar over the melted butter.
  4. Arrange 7 to 8 pineapple slices on top of the brown sugar layer (place one ring in the center and the rest around it). Place a cherry in the center of each pineapple ring, and add extra cherries in any open spaces between the slices. Set the pan aside.

2. Make the Batter

  1. In a medium bowl, whisk together the flour, baking powder, and salt.
  2. In a large bowl using an electric mixer, beat the softened butter and granulated sugar together on medium speed for about 2 minutes until light and fluffy.
  3. Beat in the eggs one at a time, followed by the vanilla extract, scraping down the sides of the bowl as needed.
  4. With the mixer on low speed, add the dry ingredients in three additions, alternating with the milk and reserved pineapple juice (starting and ending with the dry ingredients). Mix just until combined; do not overmix.

3. Bake

  1. Carefully spoon the cake batter over the fruit layer, gently spreading it with a spatula so the pineapples and cherries stay in place.
  2. Bake for 40 to 45 minutes, or until a toothpick inserted into the center of the cake comes out clean (or with a few moist crumbs). If the top browns too quickly toward the end, loosely tent a piece of aluminum foil over the top.

4. Cool and Invert

  1. Remove the cake from the oven and let it cool in the pan on a wire rack for 10 to 15 minutes (this gives the caramel time to set slightly without sticking).
  2. Run a butter knife around the inside edge of the pan to loosen the sides.
  3. Place a large serving plate upside down over the top of the pan. Firmly holding the pan and plate together, invert them in one smooth motion.
  4. Let the pan rest upside down for 1 to 2 minutes so all the caramel drips down, then slowly lift off the pan. If any fruit sticks to the pan, simply lift it out with a spoon and place it back onto the cake.

Pro Tips for Success

  • Dry the Cherries & Pineapples: Pat the pineapple slices and maraschino cherries thoroughly with paper towels before placing them on the sugar layer. Excessive liquid can make the caramelized top soggy.
  • Serve Warm: Pineapple upside-down cake is best enjoyed warm or at room temperature, paired perfectly with a scoop of vanilla ice cream or a dollop of whipped cream.

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