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Pineapple Upside Down Sugar Cookies Recipe

5 from 115 reviews

These Pineapple Upside Down Sugar Cookies combine the classic charm of pineapple upside down cake with the soft, sweet delight of sugar cookies. Featuring tender sugar cookie dough topped with juicy pineapple rings and a sprinkle of sugar, they bake to golden perfection for a unique and delicious treat perfect for any occasion.

Ingredients

Scale

Cookie Dough

  • 1 cup unsalted butter (softened)
  • 1 cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract (optional)
  • 2 cups all-purpose flour (or gluten-free blend)
  • 1 teaspoon baking soda
  • 1/2 teaspoon salt

Topping

  • 1 can canned pineapple rings (well-drained)
  • 2 tablespoons additional sugar for sprinkling

Instructions

  1. Preheat the oven: Set your oven to 350°F (180°C) and prepare your baking trays by lining them with parchment paper to prevent sticking.
  2. Cream butter and sugar: In a mixing bowl, cream the softened unsalted butter and granulated sugar together for 2-3 minutes until the mixture becomes light and fluffy, which helps incorporate air for tender cookies.
  3. Add wet ingredients: Beat in the large egg and vanilla extract (if using) thoroughly until fully combined, ensuring a smooth batter.
  4. Combine dry ingredients and mix: In a separate bowl, whisk together the flour, baking soda, and salt. Gradually add this dry mixture to the wet ingredients, mixing gently until a soft cookie dough forms without overworking it.
  5. Scoop dough onto trays: Using a tablespoon or cookie scoop, measure out approximately 2 tablespoons of dough per cookie and place the mounds evenly spaced on the prepared baking trays.
  6. Add pineapple rings: Gently press a well-drained pineapple ring into each dough mound, slightly flattening the dough around the pineapple for stability.
  7. Sprinkle sugar topping: Generously sprinkle the additional 2 tablespoons of granulated sugar over the pineapple rings to create a caramelized sweet topping as they bake.
  8. Bake cookies: Place the trays in the preheated oven and bake for 11-13 minutes, or until the cookie edges turn golden and the centers are set but still soft.
  9. Cool the cookies: Allow the cookies to cool on the baking tray for a few minutes to firm up before transferring them to a wire rack for complete cooling to avoid breaking.

Notes

  • Ensure pineapple rings are well-drained to prevent soggy cookies.
  • For a gluten-free option, substitute all-purpose flour with a cup-for-cup gluten-free baking blend.
  • Press the pineapple gently so the cookie dough holds the topping without spreading too much during baking.
  • Store cooled cookies in an airtight container at room temperature for up to 4 days.
  • Vanilla extract is optional but adds a lovely depth of flavor.

Keywords: pineapple upside down cookies, sugar cookies, pineapple cookies, easy pineapple dessert, baked cookies, fruit topped cookies