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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 a classic tropical flavor with a soft, buttery sugar cookie base for a perfect sweet treat.

Ingredients

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

Instructions

  1. Preheat your 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. Add the egg and vanilla extract, mixing well to combine.
  4. In a separate bowl, whisk together the flour, baking powder, and salt.
  5. Gradually add the dry ingredients to the wet mixture, mixing until just combined.
  6. In another bowl, toss the drained crushed pineapple with the brown sugar.
  7. Form the cookie dough into 1.5-inch balls and place them on the prepared baking sheet, spacing them about 2 inches apart.
  8. Flatten each cookie ball slightly and top each with a teaspoon of the pineapple and some brown sugar mixture.
  9. Press a halved maraschino cherry into the center of each cookie, if using.
  10. Bake for 12-15 minutes, or until the edges are lightly golden.
  11. Allow the cookies to cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely.

Notes

For an extra caramelized flavor, sprinkle a tiny pinch of brown sugar on top right before baking. These cookies pair wonderfully with a cup of hot tea or coffee.