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Pineapple Upside Down Cupcakes

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Pineapple Upside Down Cupcakes are a fun twist on the classic dessert, featuring caramelized pineapple and cherries baked beneath a moist vanilla cake. Once inverted, they reveal a beautiful golden topping that needs no frosting.

Ingredients

  • 1/4 cup unsalted butter, melted
  • 1/2 cup brown sugar
  • 12 pineapple pieces or pineapple chunks
  • 12 maraschino cherries
  • 1 1/2 cups all-purpose flour
  • 1 1/2 tsp baking powder
  • 1/4 tsp salt
  • 1/2 cup unsalted butter, softened
  • 3/4 cup granulated sugar
  • 2 eggs
  • 1 tsp vanilla extract
  • 1/4 cup pineapple juice
  • 1/4 cup whole milk

Instructions

  1. Preheat the oven to 350°F (175°C) and thoroughly grease a 12-cup muffin tin.
  2. Divide the melted butter evenly among the muffin cups.
  3. Sprinkle brown sugar over the butter in each cup.
  4. Place a pineapple piece in each muffin cup and add a maraschino cherry in the center or alongside it.
  5. Whisk together the flour, baking powder, and salt in a medium bowl.
  6. In a large bowl, beat the softened butter and granulated sugar until light and fluffy.
  7. Add the eggs one at a time, mixing well after each addition.
  8. Stir in the vanilla extract.
  9. Gradually add the dry ingredients, alternating with the pineapple juice and milk, mixing until just combined.
  10. Spoon the batter over the pineapple topping, filling each muffin cup about three-quarters full.
  11. Bake for 20 to 25 minutes, or until a toothpick inserted into the center comes out clean.
  12. Cool in the pan for 5 minutes.
  13. Run a knife around the edges and carefully invert the cupcakes onto a cooling rack while still warm.
  14. Allow to cool completely before serving.

Notes

  • Add shredded coconut to the batter for extra tropical flavor.
  • Use crushed pineapple instead of pineapple rings for a different texture.
  • Add a splash of rum extract for a Caribbean-inspired variation.
  • Replace maraschino cherries with fresh cherries when in season.
  • Mix chopped pecans or walnuts into the brown sugar topping for added crunch.
  • Store in an airtight container in the refrigerator for up to 4 days.
  • Freeze for up to 2 months and thaw overnight before serving.
  • Invert the cupcakes while warm to prevent sticking.

Nutrition

Find it online: https://thefamilycooking.com/pineapple-upside-down-cupcakes/