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Pineapple Upside Down Sugar Cookies

Freshly prepared Pineapple Upside Down Sugar Cookies on white plate

Delight in these Pineapple Upside Down Sugar Cookies that combine classic tropical flavors with a soft, buttery cookie base for a unique twist on a beloved dessert.

Ingredients

Scale
  • 1 cup unsalted butter, softened
  • 1 cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 2 1/2 cups all-purpose flour
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon salt
  • 1/2 cup crushed pineapple, drained
  • Maraschino cherries, halved (optional)
  • 1 tablespoon brown sugar

Instructions

  1. Preheat oven to 350°F (175°C) and line a baking sheet with parchment paper.
  2. In a large bowl, cream together the softened butter and granulated sugar until light and fluffy.
  3. Beat in the egg and vanilla extract until well combined.
  4. In a separate bowl, whisk together flour, baking powder, and salt.
  5. Gradually add the dry ingredients to the wet, mixing until a soft dough forms.
  6. Roll dough into 1-inch balls and flatten slightly on the prepared baking sheet.
  7. Place a small spoonful of drained crushed pineapple on top of each cookie, sprinkle a pinch of brown sugar over the pineapple, and optionally top with a maraschino cherry half.
  8. Bake for 12–15 minutes or until edges are lightly golden.
  9. Allow cookies to cool on baking sheet for 5 minutes before transferring to a wire rack to cool completely.

Notes

For extra flavor, chill the dough for 30 minutes before baking and serve these cookies with a scoop of vanilla ice cream.