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Irresistible Pineapple Upside Down Cupcakes: A Sweet Slice of Paradise in Every Bite

pineapple upside down cupcakes

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Mini pineapple upside down cupcakes combine golden caramelized pineapple, baked cherries, and a moist vanilla cupcake batter for a sweet, tropical dessert perfect for any occasion.

Ingredients

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For the Topping:

  • 1 can of pineapple rings (12 rings)
  • 12 maraschino cherries
  • ½ cup (100 g) brown sugar
  • ¼ cup (57 g) unsalted butter, melted

For the Cupcake Batter:

  • 1½ cups (190 g) all-purpose flour
  • 1 cup (200 g) granulated sugar
  • ½ cup (113 g) unsalted butter, softened
  • 1½ tsp baking powder
  • ¼ tsp salt
  • ½ cup (120 ml) milk
  • 2 large eggs
  • 1 tsp vanilla extract
  • ¼ cup (60 ml) pineapple juice (reserved from the can)

Instructions

  1. Prepare the Topping: Grease a 12-cup muffin tin thoroughly. Add 1½ teaspoons of melted butter and brown sugar mixture to each cup, then place a pineapple ring in each compartment.
  2. Add Pineapple and Cherry: Press the pineapple rings gently into the muffin tin. Place a maraschino cherry in the center of each pineapple ring, ensuring it stays flat.
  3. Make the Batter: In a large bowl, cream the butter and sugar until fluffy. Add eggs, pineapple juice, milk, and vanilla extract, then mix in the dry ingredients until just combined.
  4. Fill the Muffin Tin: Pour the cupcake batter evenly into the prepared muffin tin, covering the pineapple and cherry. Fill each cup about three-quarters full to allow for rising.
  5. Bake the Cupcakes: Preheat the oven to 350°F (175°C) and bake for 18–22 minutes. Check doneness with a toothpick; it should come out clean when inserted.
  6. Flip and Cool: Allow the cupcakes to cool in the pan for 10 minutes. Place a baking sheet or large plate over the tin and carefully flip it over to reveal the caramelized tops.

Notes

  • Grease Generously: Ensure every crevice of the muffin tin is well-greased to prevent sticking. For best results, use a non-stick baking spray or brush melted butter thorough.
  • Trim the Pineapple Rings: If the pineapple rings are too large for the muffin tin, trim them slightly to fit snugly. This ensures a neat presentation when flipped.
  • Flip While Warm: Allow the cupcakes to cool in the pan for 10 minutes before flipping. Flipping them while still warm helps the caramelized topping release easily.

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