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Pineapple Upside-Down Sugar Cookies

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Delicious handheld desserts featuring caramelized pineapple and maraschino cherries on a tender sugar cookie base, baked in a muffin tin.

Ingredients

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  • 1/2 cup unsalted butter, melted
  • 1/2 cup packed brown sugar
  • 1 can (20 oz) pineapple slices, drained and cut into small pieces
  • Maraschino cherries, halved
  • 1 cup unsalted butter, softened
  • 1 cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 2 1/2 cups all-purpose flour
  • 1 teaspoon baking powder
  • 1/4 teaspoon salt

Instructions

  1. Preheat your oven to 350°F (175°C) and lightly grease or line a muffin tin with parchment rounds.
  2. Mix the melted butter and brown sugar until combined, then spoon about 1 tablespoon into each muffin cup.
  3. Place small pieces of drained pineapple on top of the brown sugar mixture, then press half of a maraschino cherry into the center of each cup.
  4. Cream the softened butter and granulated sugar together until light and fluffy.
  5. Beat in the egg and vanilla extract until well combined.
  6. Whisk together the flour, baking powder, and salt in a separate bowl.
  7. Gradually add the dry ingredients to the wet ingredients, mixing until a soft dough forms.
  8. Press about 1 1/2 tablespoons of cookie dough over the pineapple and cherry topping in each muffin cup.
  9. Bake for 12 to 15 minutes, or until the edges are lightly golden.
  10. Cool the cookies in the muffin tin for 5 minutes, then carefully flip the tin over onto a parchment-lined surface.

Notes

For best results, drain the pineapple well and use room-temperature butter for the cookie dough.

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