Pineapple Upside Down Cupcakes

Ingredients


For the topping:

  • 1/4 cup (½ stick) unsalted butter, melted
  • 1/2 cup brown sugar (light or dark)
  • 6 pineapple rings, cut in halves or quarters
  • 12 maraschino cherries

For the cupcake batter:

  • 1 box yellow cake mix (plus ingredients listed on the box: usually 3 eggs, 1/3 cup oil, and 1 cup water)
    —OR—
  • Make from scratch:
    • 1½ cups all-purpose flour
    • 1½ tsp baking powder
    • 1/4 tsp salt
    • 1/2 cup unsalted butter, softened
    • 3/4 cup granulated sugar
    • 2 large eggs
    • 1/2 cup milk
    • 1 tsp vanilla extract
    • 1/4 cup reserved pineapple juice (from the can)

Instructions

  1. Preheat oven to 350°F (175°C). Lightly grease a 12-cup muffin tin or line with cupcake liners (remove liners before adding topping).
  2. Spoon 1 tsp melted butter into the bottom of each muffin cup. Sprinkle 1 tbsp brown sugar over the butter.
  3. Place a piece of pineapple (half or quarter ring) into each cup and center a cherry in the middle.
  4. Prepare cake batter according to box directions or from scratch. Pour the batter over the pineapple/cherry layer in each cup, filling about 2/3 full.
  5. Bake for 20–25 minutes or until a toothpick comes out clean.
  6. Cool in the pan for 5 minutes. Then, place a baking sheet or large tray over the muffin tin and carefully invert to release cupcakes.
  7. Let cool slightly, and enjoy warm or at room temperature!

💡 Tip: These are delicious served slightly warm with a scoop of vanilla ice cream.

Would you like a printable card or a version with a from-scratch batter only?

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