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Pineapple Upside Down Sugar Cookies

These Pineapple Upside Down Sugar Cookies combine the classic tropical flavors of pineapple and brown sugar with a soft, buttery cookie base for a delightful twist on a favorite dessert.

Ingredients

Scale
  • 1 cup unsalted butter, softened
  • 1 cup granulated sugar
  • 1/2 cup packed brown sugar
  • 2 large eggs
  • 1 tsp vanilla extract
  • 3 cups all-purpose flour
  • 1 tsp baking powder
  • 1/2 tsp baking soda
  • 1/2 tsp salt
  • 1 cup crushed pineapple, drained
  • 1/4 cup brown sugar (for topping)
  • Maraschino cherries, halved (optional, for garnish)

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 butter, granulated sugar, and brown sugar until light and fluffy.
  3. Beat in the eggs one at a time, then stir in the vanilla extract.
  4. In a separate bowl, whisk together the flour, baking powder, baking soda, and salt.
  5. Gradually add the dry ingredients to the wet ingredients, mixing until just combined.
  6. Fold in the drained crushed pineapple gently to distribute evenly.
  7. Drop tablespoon-sized dough balls onto the prepared baking sheet, spacing them about 2 inches apart.
  8. Sprinkle a pinch of brown sugar on top of each cookie and gently press to slightly flatten.
  9. Optionally, place a halved maraschino cherry on top of each cookie.
  10. Bake for 12-15 minutes, until edges are lightly golden.
  11. Remove from oven and allow to cool on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely.

Notes

For an extra caramelized flavor, broil the cookies for 1-2 minutes after baking, watching carefully to prevent burning.