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Pineapple Upside Down Sugar Cookies Recipe

4.6 from 122 reviews

These Pineapple Upside Down Sugar Cookies offer a delightful twist on classic sugar cookies by topping each bite with a sweet pineapple ring, creating a perfect balance of buttery, sugary dough and fruity freshness. Ideal for parties or a tropical-inspired treat, these cookies are easy to make and guaranteed to impress.

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 facilitate even cooking.
  2. Cream Butter and Sugar: In a mixing bowl, cream the softened unsalted butter and granulated sugar together using a hand mixer or stand mixer until the mixture is light and fluffy, about 2-3 minutes. This step ensures a tender cookie texture.
  3. Add Egg and Vanilla: Beat in the large egg and vanilla extract (if using) thoroughly until fully combined, which will enrich the dough’s flavor and help with binding.
  4. Mix Dry Ingredients: In a separate bowl, whisk together the all-purpose flour, baking soda, and salt to evenly distribute the leavening and seasoning.
  5. Combine Wet and Dry: Gradually add the dry ingredients into the wet mixture, stirring gently until a soft dough forms. Avoid overmixing to keep cookies tender.
  6. Form Dough Mounds: Scoop approximately 2 tablespoons of dough for each cookie and place them spaced out 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, slightly flattening the dough to secure the pineapple in place.
  8. Sprinkle Sugar: Sprinkling an additional 2 tablespoons of sugar over the pineapple adds sweetness and creates a lightly caramelized finish on top.
  9. Bake Cookies: Bake in the preheated oven for 11-13 minutes, or until the edges turn golden and the centers appear set, indicating perfect doneness.
  10. Cool Cookies: Let the cookies cool on the baking tray for a few minutes to firm up before transferring them to a wire rack to cool completely, preventing sogginess and preserving crispness.

Notes

  • Ensure pineapples are well-drained to prevent excess moisture from making the cookies soggy.
  • If you prefer a more intense pineapple flavor, drizzle a little pineapple juice on top before baking.
  • For a gluten-free version, substitute with a gluten-free all-purpose flour blend.
  • Store cookies in an airtight container at room temperature for up to 3 days.
  • Vanilla extract is optional but recommended to enhance flavor complexity.

Keywords: pineapple sugar cookies, pineapple upside down cookies, sugar cookies with pineapple, tropical cookies, baked pineapple cookies, easy cookie recipes