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Pineapple Upside Down Sugar Cookies Recipe

4.8 from 124 reviews

These Pineapple Upside Down Sugar Cookies combine the classic tropical flavors of pineapple with a soft, buttery sugar cookie base. Each cookie is topped with a juicy pineapple ring and a sprinkle of sugar, then baked to golden perfection, creating a delightful bite that’s both sweet and tangy.

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 line baking trays with parchment paper to prevent sticking and ensure even baking.
  2. Cream butter and sugar: Using a mixer, cream the softened unsalted butter and granulated sugar together until the mixture is light and fluffy, which usually takes about 2-3 minutes. This helps create a tender cookie texture.
  3. Add egg and vanilla: Beat in the large egg and vanilla extract (if using) until the mixture is fully combined and smooth.
  4. Mix dry ingredients: In a separate bowl, whisk together the all-purpose flour, baking soda, and salt to distribute the leavening agent and salt evenly.
  5. Combine wet and dry ingredients: Gradually add the dry ingredient mixture into the wet mixture, stirring carefully until a soft cookie dough forms without overmixing to keep cookies tender.
  6. Portion the dough: Scoop about 2 tablespoons of dough per cookie onto the prepared trays, spacing them apart to allow for spreading during baking.
  7. Add pineapple topping: Gently press one well-drained pineapple ring into the center of each dough mound, slightly flattening the cookie dough to adhere.
  8. Sprinkle sugar: Generously sprinkle the additional sugar over the pineapple rings to add a caramelized sweetness as the cookies bake.
  9. Bake the cookies: Place the trays in the oven and bake for 11-13 minutes, or until the edges become golden and the centers are set but still soft.
  10. Cool: Allow the cookies to cool on the baking tray for a few minutes to firm up slightly, then transfer to a wire rack to cool completely, preventing sogginess and preserving texture.

Notes

  • Ensure pineapple rings are well-drained to prevent soggy cookies.
  • You can substitute all-purpose flour with a gluten-free blend for gluten-free cookies.
  • Vanilla extract is optional but enhances the flavor of the cookies.
  • Cookies are best enjoyed fresh but can be stored in an airtight container at room temperature for up to 3 days.
  • For a more caramelized pineapple topping, broil the cookies for 1-2 minutes after baking, watching closely to avoid burning.

Keywords: pineapple upside down cookies, sugar cookies, pineapple cookies, tropical cookies, baked cookies, dessert recipes