Print

Pineapple Upside Down Sugar Cookies

These Pineapple Upside Down Sugar Cookies combine the classic tropical flavors of pineapple and brown sugar caramel in a soft, buttery sugar cookie perfect for any occasion.

Ingredients

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

Instructions

  1. Preheat the 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 the flour, baking powder, and salt.
  5. Gradually add the dry ingredients to the wet ingredients, mixing until a soft dough forms.
  6. In a small bowl, stir the drained crushed pineapple with the brown sugar.
  7. Take tablespoon-sized portions of dough and flatten slightly. Place a teaspoon of the pineapple and brown sugar mixture on top, then gently fold the dough around it, sealing the pineapple inside.
  8. Place the filled dough balls onto the prepared baking sheet, spacing them about 2 inches apart. Optionally, press a halved maraschino cherry on top of each cookie.
  9. Bake for 12–15 minutes or until the 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 extra caramel flavor, drizzle warmed brown sugar syrup over cooled cookies before serving.