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Pineapple Upside Down Sugar Cookies That Delight Every Bite Recipe

4.7 from 130 reviews

These Pineapple Upside Down Sugar Cookies combine the classic tropical flavors of pineapple with the sweet, buttery goodness of sugar cookies. Perfectly soft and chewy, each cookie is topped with a caramelized pineapple ring that adds a delightful burst of juicy sweetness in every bite. Ideal for summer gatherings or a sweet treat anytime, these cookies bring a fun twist to traditional sugar cookies.

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 Oven: Preheat your oven to 350°F (180°C) and line your baking trays with parchment paper to prevent sticking.
  2. Cream Butter and Sugar: In a large mixing bowl, cream the softened unsalted butter and granulated sugar together using a hand or stand mixer until light and fluffy, about 2-3 minutes.
  3. Add Egg and Vanilla: Beat in the large egg and vanilla extract (if using) until the mixture is well combined and smooth.
  4. Combine Dry Ingredients: In a separate bowl, whisk together the all-purpose flour, baking soda, and salt to evenly distribute the leavening agents and salt.
  5. Mix Dough: Gradually add the dry ingredients into the wet ingredients, mixing gently until a soft dough forms without overmixing.
  6. Form Cookies: Scoop 2 tablespoons of dough for each cookie and place them onto the prepared baking trays, leaving enough space between each for spreading.
  7. Add Pineapple Topping: Gently press one well-drained canned pineapple ring into the top of each dough mound, flattening the cookie slightly.
  8. Sprinkle Sugar: Generously sprinkle the additional 2 tablespoons of granulated sugar on top of each pineapple ring to help caramelize during baking.
  9. Bake: Bake the cookies in the preheated oven for 11-13 minutes, or until the edges turn golden brown and the centers are firmly set.
  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 they set perfectly.

Notes

  • Ensure pineapple rings are well-drained to avoid soggy cookies.
  • You can substitute vanilla extract with almond extract for a different flavor profile.
  • For gluten-free options, use a 1:1 gluten-free flour blend.
  • Store cookies in an airtight container to maintain freshness for up to 3 days.
  • These cookies are best enjoyed within a day or two for optimal texture.

Keywords: pineapple upside down cookies, sugar cookies, pineapple cookies, tropical cookies, baked cookies, dessert recipe, sweet cookies, pineapple dessert