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The Best Homemade Pineapple Upside Down Cake From Scratch

A moist slice removed from a homemade pineapple upside down cake topped with caramelized pineapple rings and maraschino cherries.
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Make this classic, moist Pineapple Upside Down Cake from scratch. It features a buttery cake base topped with perfectly caramelized pineapple rings and cherries. This recipe delivers a showstopper dessert that honors nostalgic comfort.

Ingredients

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

Instructions

  1. Preheat your oven to 350°F (175°C). Do not grease your 9-inch round cake pan.
  2. Melt 1/2 cup butter in a small saucepan over medium heat. Pour the melted butter into the bottom of the cake pan.
  3. Sprinkle the brown sugar evenly over the melted butter.
  4. Arrange the pineapple slices on top of the brown sugar mixture in a single layer. Place one maraschino cherry in the center of each pineapple ring, and place any remaining cherries around the edges.
  5. In a medium bowl, whisk together the flour, baking powder, and salt. Set this dry mixture aside.
  6. In a large bowl, cream together the 1/2 cup softened butter and granulated sugar until light and fluffy.
  7. Beat in the eggs one at a time, mixing well after each addition. Stir in the vanilla extract.
  8. In a small bowl, whisk together the milk and the reserved pineapple juice.
  9. Add the dry ingredients to the wet ingredients in three additions, alternating with the milk/juice mixture, beginning and ending with the dry ingredients. Mix until just combined; do not overmix.
  10. Carefully pour the cake batter over the pineapple and cherry layer in the pan. Spread the batter evenly.
  11. Bake for 40 to 45 minutes, or until a wooden pick inserted into the center comes out clean.
  12. Let the cake cool in the pan on a wire rack for exactly 10 minutes.
  13. Place a serving plate upside down over the cake pan. Wearing oven mitts, firmly hold the plate and the pan together. Quickly flip the cake over onto the plate. Lift the pan off carefully. If any topping sticks, gently place the fruit back onto the cake.
  14. Serve warm or at room temperature.

Notes

  • Allow the cake to cool for 10 minutes before flipping. This cooling time is crucial for the caramel topping to set slightly, preventing it from running off completely.
  • For an extra moist cake, substitute sour cream for the milk in the batter.
  • Serve this classic pineapple cake with a dollop of fresh whipped cream or vanilla ice cream.

Nutrition

Find it online: https://completelyyummy.com/best-pineapple-upside-down-cake-from-scratch/