Pineapple Upside-Down Cupcakes

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These adorable individual-sized treats are a fun twist on the classic pineapple upside-down cake. Perfectly moist and sweet, each cupcake has a caramelized pineapple topping that will make them a crowd favorite.

Ingredients

Topping:

  • 1/4 cup unsalted butter (melted)
  • 1/2 cup brown sugar (packed)
  • 6 pineapple rings (canned, cut into small chunks)
  • 12 maraschino cherries

Cupcake Batter:

  • 1 1/2 cups all-purpose flour
  • 1 cup granulated sugar
  • 1/2 cup unsalted butter (softened)
  • 2 teaspoons baking powder
  • 1/2 teaspoon salt
  • 1/2 cup pineapple juice (reserved from the can)
  • 1/4 cup milk
  • 2 large eggs
  • 1 teaspoon vanilla extract

Instructions

1. Preheat Oven

  1. Preheat your oven to 350°F (175°C).
  2. Grease a 12-cup muffin tin or line it with cupcake liners (note: liners will prevent the topping from caramelizing directly on the cupcake).

2. Prepare the Topping

  1. In a small bowl, mix the melted butter and brown sugar.
  2. Spoon about 1 teaspoon of the mixture into the bottom of each muffin cup.
  3. Place 3–4 pineapple chunks and a maraschino cherry in each cup, arranging them decoratively.

3. Make the Cupcake Batter

  1. In a large mixing bowl, combine the flour, sugar, baking powder, and salt.
  2. Add the softened butter, pineapple juice, milk, eggs, and vanilla extract.
  3. Beat with a hand or stand mixer on medium speed until smooth and well combined (about 2 minutes).

4. Assemble and Bake

  1. Spoon the batter evenly over the pineapple topping in the muffin tin, filling each cup about 3/4 full.
  2. Bake in the preheated oven for 20–25 minutes, or until a toothpick inserted into the center of a cupcake comes out clean.

5. Cool and Invert

  1. Allow the cupcakes to cool in the pan for about 5 minutes.
  2. Run a knife around the edges of each cupcake to loosen them.
  3. Place a baking sheet or plate over the muffin tin, then carefully invert to release the cupcakes.

Serving Suggestions

  • Serve warm or at room temperature.
  • Add a dollop of whipped cream or a scoop of vanilla ice cream for an extra indulgent treat.

Tips for Success

  • Prevent sticking: Grease the muffin tin thoroughly, especially if not using liners.
  • Avoid overfilling: Ensure the batter doesn’t go over 3/4 full to prevent spilling during baking.
  • For extra flavor: Use dark brown sugar for a richer caramel taste.

These pineapple upside-down cupcakes are easy to make and absolutely delightful for any occasion. Perfectly portioned and irresistibly delicious! 🍍🧁✨

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