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Pineapple Upside Sugar Cookies

Posted on April 1, 2025

Pineapple Upside Sugar Cookies are a fun twist on the traditional pineapple upside-down cake, but in cookie form! These cookies are sweet, chewy, and have a delightful tropical flavor thanks to the pineapple. They feature a pineapple ring, maraschino cherry, and a buttery sugar cookie base. Here’s how to make them:

Pineapple Upside Sugar Cookies

Ingredients:

For the Cookie Base:

  • 2 1/2 cups all-purpose flour
  • 1/2 teaspoon baking soda
  • 1/2 teaspoon baking powder
  • 1 cup unsalted butter, softened
  • 1 cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 1 tablespoon milk

For the Topping:

  • 1 can (8 oz) pineapple rings, drained
  • 1/4 cup maraschino cherries, halved
  • 1/4 cup brown sugar (light or dark)
  • 1 tablespoon unsalted butter, melted

Instructions:

  1. Preheat the oven:
    Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper or silicone baking mats.
  2. Prepare the cookie dough:
    • In a medium bowl, whisk together the flour, baking soda, and baking powder. Set aside.
    • In a separate large mixing bowl, beat the softened butter and granulated sugar together using an electric mixer until light and fluffy (about 2-3 minutes).
    • Add the egg, vanilla extract, and milk, and continue to beat until fully combined.
    • Gradually add the dry ingredients to the wet ingredients, mixing until the dough comes together.
  3. Prepare the cookie base on the baking sheet:
    • Roll the dough into balls (about 1 1/2 tablespoons of dough each) and place them on the prepared baking sheet about 2 inches apart.
    • Slightly flatten each dough ball with the bottom of a glass or your fingers to form a round shape.
  4. Prepare the pineapple topping:
    • In a small bowl, combine the brown sugar and melted butter. Stir until smooth.
    • Cut the pineapple rings into halves or quarters, depending on the size you want them to be.
    • Place one pineapple piece on top of each flattened cookie, pressing it gently into the dough.
    • Spoon a small amount of the brown sugar-butter mixture over the pineapple, then place a maraschino cherry half in the center of the pineapple ring.
  5. Bake the cookies:
    • Bake the cookies in the preheated oven for 10-12 minutes, or until the edges of the cookies are lightly golden brown.
    • Once baked, remove the cookies from the oven and allow them to cool on the baking sheet for about 5 minutes before transferring them to a wire rack to cool completely.
  6. Serve:
    • Enjoy the cookies warm or at room temperature! They are best served fresh but can be stored in an airtight container for a few days.

Tips:

  • Pineapple rings: Make sure to drain the pineapple well so the cookies don’t become too soggy.
  • Maraschino cherries: You can substitute maraschino cherries with dried cherries or candied cherries for a different flavor if you prefer.
  • Make them ahead: You can prepare the cookie dough in advance and refrigerate it for up to 2 days before baking.

These Pineapple Upside Sugar Cookies are a delightful and tropical twist on a classic treat, perfect for a summer dessert, picnic, or holiday gathering. Enjoy the sweet and fruity flavors!

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