Pineapple Upside Down is easy to make from scratch and incredibly delicious. With moist yellow cake and caramelized pineapples and maraschino cherries, it’s as pretty as it is tasty!

Ingredients

For the Topping:

  • 5 tablespoons butter
  • ¾ cup light brown sugar, packed
  • 2 teaspoons lemon juice
  • 7 pineapple rings
  • 7 maraschino cherries

For the Cake:

  • ½ cup butter, room temperature
  • 2 tablespoons vegetable oil
  • 1 cup granulated sugar
  • ¼ cup light brown sugar, packed
  • 2 large eggs
  • 2 cups flour
  • 1 tablespoon baking powder
  • ½ teaspoon salt
  • ¼ cup milk
  • ¼ cup sour cream
  • ¼ cup pineapple juice (from the canned pineapples)
  • 2 teaspoons vanilla extract

Instructions

  1. In a skillet over medium heat, add the butter and brown sugar. Cook, stirring regularly, until melted and bubbling. The mixture will be grainy.
  2. Stir in the lemon juice and cook, stirring regularly, until the mixture is bubbly and fluid.
  3. Remove pan from the heat and transfer the caramel to a 9 x 2-inch round baking dish, swirling to cover the bottom of the pan.
  4. Arrange the pineapple rings in the syrup close together but not overlapping. Place a maraschino cherry in each pineapple hole. Set aside.
  5. In a large bowl, add the room-temperature butter, vegetable oil, granulated sugar, and brown sugar. Using a hand mixer at medium speed, beat until creamy.

Add the eggs one at a time, beat well after each addition.

6. In a separate bowl, sift together the flour, baking powder, and salt. 

7. In another bowl, combine milk, sour cream, pineapple juice, and vanilla extract. Whisk until blended.

8. Beginning and ending with the flour mixture, add flour mixture and milk mixture alternately to the egg mixture. Beat at low speed with every addition. The batter will be thick.

9. Spoon the batter over the pineapples, carefully as not to shift or move the fruits. Using a spatula, spread and smoothen it evenly.

10. Bake in a preheated 350 F oven for about 45 to 50 minutes or until golden brown and a toothpick inserted in the center comes out clean.

11. Remove from the oven and run a small spatula around the cake to loosen.

12. Place a serving platter over the baking pan and using hand mittens, carefully invert and turn out the cake onto the platter. Brown sugar topping will be very hot.

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