Print

Pineapple Upside Down Sugar Cookies That Delight Every Bite Recipe

4.6 from 95 reviews

These Pineapple Upside Down Sugar Cookies combine the classic flavors of pineapple upside down cake with the simplicity of sugar cookies. Soft, buttery dough is topped with juicy pineapple rings and a sprinkle of sugar, resulting in a delightful, fruity twist on a traditional cookie that’s 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 Oven: 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 large bowl, cream the softened unsalted butter and granulated sugar together until the mixture is light and fluffy, which usually takes about 2-3 minutes using a hand or stand mixer.
  3. Add Egg and Vanilla: Beat in the large egg and vanilla extract (if using) until the ingredients are fully combined, ensuring an even texture.
  4. Combine Dry Ingredients: In a separate bowl, whisk together the all-purpose flour, baking soda, and salt to distribute the leavening agents evenly.
  5. Mix Dry and Wet Ingredients: Gradually add the dry ingredient mixture into the wet mixture, stirring until a soft dough forms without overmixing.
  6. Portion the Dough: Scoop approximately 2 tablespoons of dough for each cookie and place them spaced apart on the prepared baking trays to allow for spreading during baking.
  7. Add Pineapple Rings: Gently press one well-drained pineapple ring into the top of each dough mound, flattening the dough slightly to adhere the pineapple.
  8. Sprinkle Sugar: Generously sprinkle 2 tablespoons of additional granulated sugar over the pineapple rings to create a caramelized sweetness when baked.
  9. Bake: 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 without being overly firm.
  10. Cool: Allow the cookies to cool on the baking trays for a few minutes before transferring them to wire racks for complete cooling, which helps them set perfectly.

Notes

  • Make sure the pineapple rings are well-drained to prevent the dough from becoming soggy.
  • The vanilla extract is optional but adds a lovely depth of flavor to the cookies.
  • You can substitute all-purpose flour with a gluten-free flour blend to make these cookies gluten-free.
  • Store cooled cookies in an airtight container at room temperature for up to 5 days.
  • For extra caramelization, broil for 1-2 minutes after baking, watching carefully to avoid burning.

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