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The Ultimate Classic & Easy Pineapple Upside Down Cake (Moist & Caramelized)

A moist slice of pineapple upside down cake topped with caramelized pineapple rings and bright red maraschino cherries.
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Make this classic, moist Pineapple Upside Down Cake with a rich, buttery, caramelized pineapple topping. This simple recipe is perfect for family gatherings or any time you want a nostalgic, impressive dessert.

Ingredients

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  • 1/2 cup unsalted butter
  • 3/4 cup packed light brown sugar
  • 1 (20 ounce) can pineapple slices in juice, drained (reserve juice)
  • 10 maraschino cherries, drained
  • 1 1/2 cups all-purpose flour
  • 1 1/2 teaspoons baking powder
  • 1/2 teaspoon salt
  • 1/2 cup (1 stick) unsalted butter, softened
  • 3/4 cup granulated sugar
  • 2 large eggs
  • 1 teaspoon vanilla extract
  • 1/2 cup milk
  • 1/4 cup reserved pineapple juice

Instructions

  1. Preheat your oven to 350°F (175°C). Lightly grease a 9-inch round cake pan.
  2. In a small saucepan over medium heat, melt 1/2 cup of butter. Stir in the brown sugar until dissolved, creating a thick syrup. Pour this mixture evenly into the bottom of the prepared cake pan.
  3. Arrange the pineapple slices over the brown sugar mixture in the bottom of the pan. Place one maraschino cherry in the center of each pineapple ring.
  4. In a medium bowl, whisk together the flour, baking powder, and salt. Set this dry mixture aside.
  5. In a separate large bowl, cream together the softened 1/2 cup of butter and the granulated sugar until light and fluffy.
  6. Beat in the eggs one at a time, mixing well after each addition. Stir in the vanilla extract.
  7. In a small bowl, whisk together the milk and the reserved pineapple juice.
  8. Gradually add the dry ingredients to the wet ingredients, alternating with the milk mixture, beginning and ending with the dry ingredients. Mix until just combined; do not overmix.
  9. Gently spoon the cake batter over the pineapple and cherry layer in the pan, spreading it evenly without disturbing the fruit layer underneath.
  10. Bake for 35 to 40 minutes, or until a toothpick inserted into the center comes out clean.
  11. Let the cake cool in the pan on a wire rack for 10 minutes.
  12. Place a serving plate upside down over the cake pan. Carefully invert the cake onto the plate. Lift the pan away slowly. If any topping sticks, gently place the fruit back onto the cake. Serve warm or at room temperature.

Notes

  • For an even richer flavor, substitute the milk and pineapple juice with buttermilk.
  • If you prefer a Bundt cake format, grease and flour a Bundt pan well and adjust baking time as needed, checking for doneness around 45 minutes.
  • This cake keeps well covered at room temperature for up to two days.

Nutrition

Find it online: https://mistyplate.com/pineapple-upside-down-cake-recipe/