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Pineapple Upside Sugar Cookies Recipe

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4.8 from 98 reviews

These Pineapple Upside Sugar Cookies are a delightful twist on classic sugar cookies, featuring a sweet, juicy pineapple ring atop each cookie. Soft, buttery, and lightly golden with a hint of vanilla, these cookies offer a tropical flair perfect for any occasion.

Ingredients

Cookie Dough

  • 1 cup unsalted butter, softened
  • 1 cup granulated sugar
  • 1 egg
  • 1 tsp vanilla extract
  • 2½ cups all-purpose flour
  • ½ tsp baking soda
  • ¼ tsp salt

Topping

  • 10–12 canned pineapple rings, well-drained and patted dry
  • Additional sugar for sprinkling

Instructions

  1. Preheat the oven: Heat your oven to 350°F (175°C) and line baking sheets with parchment paper to prevent sticking and ensure even baking.
  2. Cream butter and sugar: In a large mixing bowl, beat the softened unsalted butter and granulated sugar together until the mixture is light and fluffy, which will ensure tender cookies.
  3. Add egg and vanilla: Incorporate the egg and vanilla extract into the creamed mixture, blending thoroughly to combine all flavors.
  4. Mix dry ingredients: In a separate bowl, whisk together the all-purpose flour, baking soda, and salt ensuring even distribution of the leavening agents and salt throughout the flour.
  5. Combine wet and dry ingredients: Gradually add the dry ingredients to the butter mixture, mixing gently until a soft dough forms without overmixing to keep the cookies tender.
  6. Shape the cookies: Roll the dough into approximately 1½ tablespoon-sized balls. Place them on the prepared baking sheets and slightly flatten each ball into a disk shape to create a base for the pineapple.
  7. Add pineapple topping: Carefully place a well-drained and patted dry canned pineapple ring on top of each dough disk, pressing gently to secure it without squishing the dough.
  8. Sprinkle sugar: Lightly dust the pineapple rings with additional granulated sugar to add sparkle and a bit of extra sweetness.
  9. Bake: Place the baking sheets in the oven and bake for 12 to 14 minutes, or until the edges of the cookies turn golden brown.
  10. Cool and serve: Allow the cookies to cool on the baking sheets for about 5 minutes before transferring them onto wire racks to cool completely. This prevents the cookies from breaking and helps set their shape.

Notes

  • Ensure the pineapple rings are well-drained and patted dry to avoid soggy cookies.
  • Use parchment paper or silicone mats to prevent sticking and facilitate easy cleanup.
  • You can sprinkle a little cinnamon on the pineapple for an extra layer of flavor.
  • Store cookies in an airtight container at room temperature for up to 4 days.
  • For crunchier cookies, bake an extra 1-2 minutes but watch closely to prevent burning.