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Pineapple Upside Sugar Cookies: Divine Tropical Treat

Pineapple Upside Sugar Cookies

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This recipe for Pineapple Upside Sugar Cookies takes you on a sweet journey to your grandmother’s kitchen. These cookies are a delightful blend of soft sugar cookie texture and the tropical flavor of pineapple, inspired by classic pineapple upside-down cake.

Ingredients

Scale
  • 1 cup unsalted butter, softened
  • 1 1/2 cups granulated sugar
  • 2 large eggs
  • 1 teaspoon vanilla extract
  • 2 3/4 cups all-purpose flour
  • 1 teaspoon baking soda
  • 1/2 teaspoon salt
  • 1/2 cup pineapple juice (from canned pineapple, drained)
  • 1/2 cup finely chopped pineapple (canned or fresh)
  • 1/2 cup packed light brown sugar
  • 1/4 cup unsalted butter, melted
  • 1/4 cup pineapple juice
  • 1/2 cup maraschino cherries, halved (optional)

Instructions

  1. Preheat your oven to 375°F (190°C). Line baking sheets with parchment paper.
  2. In a large bowl, cream together softened butter and granulated 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 flour, baking soda, and salt.
  5. Gradually add the dry ingredients to the wet ingredients, mixing until just combined.
  6. Stir in the 1/2 cup pineapple juice and 1/2 cup chopped pineapple until a soft dough forms.
  7. Chill the dough for at least 30 minutes.
  8. While the dough chills, prepare the topping. In a small bowl, combine the 1/2 cup packed light brown sugar, 1/4 cup melted butter, and 1/4 cup pineapple juice. Mix well.
  9. Roll out the chilled dough on a lightly floured surface to about 1/4-inch thickness. Cut out desired shapes using cookie cutters.
  10. Place the cookie cutouts onto the prepared baking sheets.
  11. Spoon a small amount of the brown sugar pineapple topping onto the center of each cookie.
  12. If using, place a maraschino cherry half on top of the topping.
  13. Bake for 10-12 minutes, or until edges are lightly golden.
  14. Let the cookies cool on the baking sheets for a few minutes before transferring them to a wire rack to cool completely.

Notes

  • For a stronger pineapple flavor, use fresh pineapple and reduce its moisture content by pressing it between paper towels.
  • Ensure your butter and eggs are at room temperature for best results when creaming butter and sugar.
  • Do not overmix the dough once the flour is added.
  • These cookies are best enjoyed within a few days of baking.
  • Consider adding a touch of lemon zest to the dough for a brighter flavor.

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