Pineapple Upside Down Cupcakes

Here’s a fun and tasty twist on a classic dessert — Pineapple Upside Down Cupcakes! These are individual-sized, moist, and loaded with that caramelized pineapple flavor. Great for parties, picnics, or just because.


🍍 Pineapple Upside Down Cupcakes

🧁 Makes: 12 cupcakes

⏱️ Prep Time: 15 minutes

⏱️ Bake Time: 20–25 minutes


🛒 Ingredients:

For the topping:

  • ¼ cup (½ stick) unsalted butter, melted
  • ½ cup brown sugar, packed
  • 6–7 pineapple rings (canned, drained)
  • 6–7 maraschino cherries, halved

For the cake:

  • 1 box yellow cake mix
  • Ingredients listed on the box (usually eggs, oil, and water)
  • 1 cup reserved pineapple juice (from the can, use instead of water if possible)

👩‍🍳 Instructions:

1. Prep Oven & Pan:

  • Preheat oven to 350°F (175°C).
  • Grease a 12-cup muffin tin (don’t use liners for this recipe).

2. Add Topping:

  • In each muffin cup, add 1 teaspoon melted butter and 1 tablespoon brown sugar.
  • Place a pineapple chunk (cut rings into pieces to fit) in the center.
  • Add half a cherry in the middle of the pineapple.

3. Make the Batter:

  • Prepare cake mix according to box directions, replacing water with pineapple juice if you can for more flavor.
  • Fill each muffin cup about ⅔ full with batter over the topping.

4. Bake:

  • Bake for 20–25 minutes, or until a toothpick comes out clean.

5. Cool & Flip:

  • Let cupcakes sit in the pan for about 5 minutes.
  • Run a knife around the edges to loosen.
  • Place a baking sheet or large cutting board over the pan and carefully invert to release the cupcakes.

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