Print

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 caramelized pineapple flavor with soft, buttery sugar cookies for a tropical twist on a beloved treat.

Ingredients

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

Instructions

  1. Preheat oven to 350°F (175°C). Line a baking sheet with parchment paper.
  2. In a small bowl, mix crushed pineapple with brown sugar and set aside to caramelize slightly.
  3. In a large bowl, cream together butter and granulated sugar until light and fluffy.
  4. Beat in the egg and vanilla extract until combined.
  5. In a separate bowl, whisk together flour, baking powder, and salt.
  6. Gradually add dry ingredients to the wet ingredients, mixing until just combined.
  7. Place a teaspoon of the pineapple-brown sugar mixture on the bottom of each cookie dough ball and gently swirl it in.
  8. Drop rounded tablespoons of dough onto the prepared baking sheet, spacing about 2 inches apart.
  9. Press a halved maraschino cherry into the center of each cookie, flattening slightly.
  10. Bake for 12-15 minutes or until the edges are golden brown.
  11. Allow cookies to cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely.

Notes

For extra richness, drizzle a simple caramel sauce over the cookies before serving or pair with a scoop of vanilla ice cream.