Pineapple Upside-Down Cupcakes Recipe


  • 3 (8-ounce) cans pineapple slices in 100% pineapple juice
  • 6 tablespoons unsalted butter, cubed
  • 1 cup firmly packed light brown sugar
  • 12 maraschino cherries, well drained
  • 3 large eggs, room temperature
  • 2 cups sugar
  • 1 cup canola oil
  • 1 cup sour cream
  • 1 teaspoon vanilla extract
  • 1 teaspoon rum extract
  • 2 1/2 cups all-purpose flour
  • 1/2 teaspoon baking powder
  • 1/2 teaspoon baking soda
  • 1/2 teaspoon kosher salt


  1. Gather the ingredients.

  2. Preheat oven to 350 F. Line bottom of 12 greased jumbo muffin cups with parchment paper or waxed paper. Grease paper and set aside.

  3. Drain pineapple slices and reserve 2 tablespoons of juice.

  4. In a small saucepan, melt butter over low heat. Stir in brown sugar and reserved pineapple juice. Cook and stir over medium heat until sugar is dissolved. Remove from heat.

  5. Spoon 1 tablespoonful of the brown sugar mixture into each muffin cup. Place a pineapple ring into each cup and insert a maraschino cherry into center of each pineapple ring.

  6. In a large bowl, beat eggs and sugar until thickened and lemon colored.

  7. Beat in oil, sour cream, vanilla extract, and rum extract until smooth.

  8. In another large bowl, combine flour, baking powder, baking soda, and salt.

  9. Add flour mixture to egg mixture and mix well.

  10. Fill prepared muffin cups two-thirds full. Bake for 28 to 32 minutes or until a toothpick inserted in the center comes out clean.

  11. Cool for 5 minutes before inverting onto wire racks to cool completely.

    (If using a 6 cup jumbo muffin pan, repeat with remaining ingredients.)

  12. Enjoy on their own, or serve with a dollop of whipped cream or a scoop of vanilla ice cream.

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