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Pineapple Upside Down Sugar Cookies That Delight Every Bite Recipe

4.8 from 141 reviews

These Pineapple Upside Down Sugar Cookies combine the classic flavors of pineapple upside down cake with the ease and convenience of cookies, delivering a delightful bite in every mouthful. Soft sugar cookie dough is topped with sweet pineapple rings and a sparkling sugar sprinkle, then baked to golden perfection.

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 granulated sugar for sprinkling

Instructions

  1. Preheat and prepare trays: Preheat your oven to 350°F (180°C) and line your baking trays with parchment paper to prevent sticking and ensure easy cleanup.
  2. Cream butter and sugar: In a mixing bowl, cream the softened unsalted butter and granulated sugar together until light and fluffy, which typically takes around 2-3 minutes using an electric mixer on medium speed.
  3. Add egg and vanilla: Beat in the large egg and vanilla extract (if using) until the mixture is well combined and smooth.
  4. Mix dry ingredients: In a separate bowl, whisk together the all-purpose flour, baking soda, and salt to evenly distribute the leavening agents and seasoning.
  5. Combine wet and dry mixtures: Gradually add the dry ingredients to the wet mixture, stirring until a soft dough forms without overmixing to ensure tender cookies.
  6. Portion dough on trays: Scoop out approximately 2 tablespoons of dough per cookie and place on the prepared baking trays, spacing them adequately to allow for spreading during baking.
  7. Add pineapple rings: Gently press one well-drained pineapple ring into the center of each mound of dough, slightly flattening the dough to secure the fruit in place.
  8. Sprinkle sugar: Generously sprinkle the additional 2 tablespoons of granulated sugar over the pineapple rings to add a sweet, caramelized finish.
  9. Bake: Bake the cookies for 11-13 minutes, or until the edges turn golden and the centers set while remaining soft.
  10. Cool: Allow the cookies to cool on the baking tray for a few minutes before transferring them to a wire rack to cool completely, ensuring the bottoms stay crisp and avoid condensation buildup.

Notes

  • For an extra indulgent treat, serve these cookies warm with a scoop of vanilla bean ice cream.
  • Make sure to drain pineapple rings thoroughly to prevent soggy cookie bases.
  • The cookies can be stored in an airtight container at room temperature for up to 3 days without losing freshness.
  • Using a gluten-free flour blend makes this recipe suitable for gluten-sensitive individuals.
  • Optional vanilla extract enhances the flavor but can be omitted if desired.

Keywords: pineapple upside down cookies, sugar cookies, pineapple cookies, easy cookie recipe, tropical dessert cookie