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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, combining the classic tropical flavors of pineapple and brown sugar caramel with a soft sugar cookie base for a deliciously unique dessert.

Ingredients

Scale
  • 1 cup unsalted butter, softened
  • 1 cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 2 ¾ cups all-purpose flour
  • 1 teaspoon baking powder
  • ¼ teaspoon salt
  • ½ cup brown sugar, packed
  • ½ cup crushed pineapple, drained
  • Maraschino cherries, halved (optional)

Instructions

  1. Preheat oven to 350°F (175°C). Line a baking sheet with parchment paper.
  2. In a large bowl, cream together the 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 the flour, baking powder, and salt.
  5. Gradually blend the dry ingredients into the wet mixture until a soft dough forms.
  6. In a small bowl, mix the brown sugar and crushed pineapple.
  7. Scoop tablespoon-sized portions of dough onto the baking sheet, then press gently to flatten.
  8. Top each cookie dough portion with a teaspoon of the pineapple and brown sugar mixture and place a cherry half if desired.
  9. Bake for 12–15 minutes or until edges are lightly golden.
  10. Allow cookies to cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely.

Notes

For an extra caramel flavor, drizzle a little melted brown sugar butter glaze over the cooled cookies before serving.