Pineapple Upside Down Cupcakes

INGREDIENTS

Topping:

  • ⅓ cup (75g) unsalted butter, melted
  • ⅔ cup (135g) packed light brown sugar
  • 12 maraschino cherries
  • 1 (20 oz) can pineapple slices, drained and each slice cut in half

Cupcake Batter:

  • 1½ cups (190g) all-purpose flour
  • ½ tsp baking powder
  • ¼ tsp baking soda
  • ¼ tsp salt
  • ½ cup (115g) unsalted butter, softened
  • ¾ cup (150g) granulated sugar
  • 2 large eggs
  • 1 tsp vanilla extract
  • ½ cup (120ml) sour cream or plain yogurt
  • ¼ cup (60ml) milk

INSTRUCTIONS

  1. Preheat oven to 350°F (175°C). Grease a 12-cup muffin pan (do not use liners).
  2. Make the topping: Spoon 1 teaspoon of melted butter into each muffin cup, then sprinkle 1 tablespoon of brown sugar on top. Press half a pineapple slice into each, followed by a maraschino cherry in the center.
  3. Make the batter: In a medium bowl, whisk together flour, baking powder, baking soda, and salt.
  4. In a large bowl, cream together softened butter and granulated sugar until light and fluffy. Add eggs one at a time, then mix in vanilla extract and sour cream.
  5. Add the dry ingredients in three additions, alternating with the milk. Mix until just combined—do not overmix.
  6. Spoon the batter over the pineapple/cherry layer, filling each cup about ¾ full.
  7. Bake for 20–25 minutes or until a toothpick inserted in the center comes out clean.
  8. Let the cupcakes rest for 5 minutes, then run a knife around the edges and carefully invert the pan onto a wire rack or tray. Allow them to cool before serving.

🎉 Enjoy warm or room temp—these mini tropical treats are perfect for any occasion!

Would you like a printable version or tips for making them ahead of time?

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