Christmas Pineapple Upside-Down Sugar Cookies

(from gabjos’s recipe box)

Prep time: 15 minutes
Cook time: 10 minutes
Serves 24 people

Categories: Cookies

Ingredients

  • For the Cookie Dough:
  • 1/2 cup unsalted butter, softened
  • 3/4 cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 1 1/2 cups all-purpose flour
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon salt
  • For the Topping:
  • 6 maraschino cherries, halved
  • 1/4 cup crushed pineapple, drained well
  • 2 tablespoons brown sugar

Directions

  1. Step 1: Prepare the Topping

  2. In a small bowl, combine the well-drained crushed pineapple and brown sugar. Stir until the pineapple is evenly coated. Set aside.

  3. Step 2: Make the Cookie Dough

  4. In a mixing bowl, cream together the softened butter and granulated sugar until light and fluffy. Beat in the egg and vanilla extract until well combined. In a separate bowl, whisk together the flour, baking powder, and salt. Gradually add the dry ingredients to the wet mixture, mixing until a soft dough forms.

  5. Step 3: Assemble the Cookies

  6. Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper. Roll the dough into 1-inch balls and place them on the prepared baking sheet, spacing them about 2 inches apart. Gently flatten each dough ball with your fingers or the back of a spoon.

  7. Step 4: Add the Topping

  8. Place a small spoonful of the pineapple-brown sugar mixture on each cookie and press a halved maraschino cherry in the center.

  9. Step 5: Bake the Cookies

  10. Bake in the preheated oven for 10-12 minutes, or until the edges are lightly golden. Allow the cookies to cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely.

  11. Serving and Storage Tips

  12. Serving:

  13. Serve these cookies fresh or at room temperature. They’re perfect for holiday cookie exchanges or as a festive treat to share with family and friends.

  14. Storage:

  15. Store leftover cookies in an airtight container at room temperature for up to 3 days. For longer storage, refrigerate for up to a week or freeze for up to a month.

  16. Helpful Notes

  17. Drain Pineapple Well: Make sure the crushed pineapple is well-drained to prevent excess moisture from affecting the cookie texture.

  18. Dough Chilling (Optional): For easier handling, chill the dough for 15-20 minutes before rolling into balls.

  19. Extra Festive Touch: Add a sprinkle of red and green sanding sugar to the cookie tops for an extra holiday sparkle.

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