8 servings

Pineapple Upside Down Cake

Recipe by: True Taste Buds

A classic vintage dessert featuring a caramelized pineapple and cherry topping over a dense, buttery vanilla cake. This 1920s nostalgia piece is made with an easy inverted baking technique.

★★★★★ 4.74 from 385 votes
PREP TIME 20 mins
COOK TIME 45 mins
TOTAL TIME 65 mins
SERVINGS 8
Pineapple Upside Down Cake

Ingredients

  • 1/4 cup Unsalted butter, melted
  • 3/4 cup Packed light brown sugar
  • 1 (20-ounce) can Sliced pineapple in juice, drained and juice reserved
  • 10 Maraschino cherries, stems removed
  • 1 1/2 cups All-purpose flour
  • 1 1/2 teaspoons Baking powder
  • 1/4 teaspoon Salt
  • 1/2 cup Unsalted butter, softened
  • 3/4 cup Granulated sugar
  • 2 Large eggs, room temperature
  • 1 teaspoon Vanilla extract
  • 1/2 cup Reserved pineapple juice

Instructions

  1. Preheat your oven to 350 degrees Fahrenheit. Pour 1/4 cup of melted unsalted butter into the bottom of an ungreased 9-inch round cake pan. Sprinkle 3/4 cup of packed light brown sugar evenly over the butter. Pat the sugar mixture down firmly with a spatula until smooth.
  2. Drain the canned pineapple rings, making sure to save the leftover juice for the batter. Place one pineapple ring squarely in the center of the pan over the brown sugar layer. Arrange the remaining 6 to 7 rings in a tight circle around the center ring. Press one maraschino cherry (stem removed) into the hole of each pineapple ring. Place additional cherries in the empty spaces between the rings.
  3. In a medium mixing bowl, measure out 1 1/2 cups of all-purpose flour. Add 1 1/2 teaspoons of baking powder and 1/4 teaspoon of salt. Whisk everything together vigorously for at least 30 seconds. Set the bowl of dry ingredients aside.
  4. In a large bowl, cream 1/2 cup of softened unsalted butter and 3/4 cup of granulated sugar on medium-high speed for 2 to 3 minutes until light and fluffy. Beat in 2 large room temperature eggs, one at a time, mixing well after each addition. Add 1 teaspoon of vanilla extract. Pour in 1/2 cup of the reserved pineapple juice from the can and mix briefly on low speed.
  5. Pour the dry flour mixture into the wet ingredients. Use a silicone spatula to gently fold the batter just until combined. Spoon the batter carefully over the prepared pineapple and cherry layer in the cake pan. Smooth the top of the batter into an even layer with the back of a spoon or a small offset spatula.
  6. Bake in the preheated 350-degree oven for 40 to 45 minutes. Insert a toothpick into the center of the cake to test for doneness. It should come out clean or with a few moist crumbs. Remove the pan from the oven and place it on a wire cooling rack. Set a timer and let the cake rest undisturbed for exactly 10 minutes.
  7. Run a butter knife around the edge of the slightly cooled cake to loosen it. Place a large, flat serving plate upside down over the top of the cake pan. Hold the pan and plate tightly together and flip them over in one quick motion. Gently lift the cake pan straight up to reveal the caramelized topping.

Notes

Always pat your pineapple rings and cherries dry to prevent a soggy caramel layer. Gently tap the filled cake pan on the counter before baking to pop trapped air bubbles. If the top of the cake browns too rapidly around the 30-minute mark, drape a loose piece of foil over the top. If any fruit sticks during the flip, carefully pry it out while warm and place it back onto the cake.

Nutrition

Calories: 340 | Carbohydrates: 52g | Protein: 4g | Fat: 14g | Saturated Fat: 8g | Cholesterol: 60mg | Sodium: 150mg | Fiber: 1g | Sugar: 38g