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Pineapple Upside Sugar Cookies Recipe

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4.9 from 69 reviews

These Pineapple Upside Sugar Cookies combine the tropical sweetness of pineapple rings with classic sugar cookie dough, baked to golden perfection. Topped with a sprinkle of sugar for an added sparkle, these cookies offer a delightful twist on the traditional sugar cookie, perfect for summer gatherings or anytime you crave a fruity, buttery treat.

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 Oven and Prepare Sheets: Preheat 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 bowl, cream the softened unsalted butter and granulated sugar together until the mixture is light and fluffy, which helps create a tender cookie texture.
  3. Add Egg and Vanilla: Beat in the egg and vanilla extract until fully combined, incorporating moisture and flavor into the cookie dough.
  4. Mix Dry Ingredients: In a separate bowl, whisk together the all-purpose flour, baking soda, and salt to evenly distribute the leavening agent and seasoning.
  5. Combine Dry and Wet Ingredients: Gradually add the dry ingredient mixture to the butter mixture, stirring until a soft dough forms, avoiding overmixing to keep cookies tender.
  6. Form Cookie Bases: Roll the dough into approximately 1½ tablespoon-sized balls, flatten each slightly to form disks, and arrange them on the prepared baking sheets, leaving space between each cookie for spreading.
  7. Add Pineapple Rings: Gently top each dough disk with a well-drained pineapple ring, pressing lightly so the pineapple adheres but dough isn’t overly compressed.
  8. Sprinkle Sugar: Sprinkle additional granulated sugar atop each pineapple ring to add a sparkling sweetness and subtle crunch.
  9. Bake Cookies: Bake in the preheated oven for 12–14 minutes or until the cookie edges turn a light golden brown, indicating they are perfectly cooked.
  10. Cool and Serve: Allow cookies to cool on the baking sheet for 5 minutes, then transfer them to a wire rack to cool completely before serving to preserve their texture.

Notes

  • Ensure pineapple rings are thoroughly drained and patted dry to prevent soggy cookies.
  • For extra flavor, consider lightly caramelizing the pineapple rings before topping the cookies.
  • These cookies store well in an airtight container for up to 3 days at room temperature.
  • Adjust baking time slightly if cookies are larger or smaller than specified.