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Pineapple Upside Down Sugar Cookies Recipe

4.5 from 70 reviews

Delightfully sweet and buttery Pineapple Upside Down Sugar Cookies combine the classic flavors of pineapple upside down cake with the convenience of cookies. Each cookie features a soft, fluffy sugar cookie base topped with a juicy pineapple ring and a sprinkle of sugar for a caramelized finish. Perfect for a tropical twist on 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 sugar for sprinkling

Instructions

  1. Preheat Oven: Set your oven to 350°F (180°C) and line baking trays with parchment paper to prevent sticking and ensure even baking.
  2. Cream Butter and Sugar: In a mixing bowl, cream the softened unsalted butter and granulated sugar together with an electric mixer or by hand until the mixture is light and fluffy, which should take about 2-3 minutes. This step is crucial for a tender cookie texture.
  3. Add Egg and Vanilla: Beat in the large egg and vanilla extract (if using) until fully combined, which adds moisture and flavor to the dough.
  4. Mix Dry Ingredients: In a separate bowl, whisk together the all-purpose flour, baking soda, and salt. This ensures the leavening agent and seasoning are evenly distributed.
  5. Combine Dry and Wet Mixtures: Gradually mix the dry ingredients into the wet mixture until a soft dough forms, being careful not to overmix to maintain tender cookies.
  6. Portion Dough: Scoop about 2 tablespoons of dough per cookie onto the prepared baking trays. Leave enough space between each mound to allow spreading during baking.
  7. Add Pineapple Rings: Gently press one pineapple ring into each dough mound, pressing just enough to slightly flatten the dough but not so much that the pineapple is submerged.
  8. Sprinkle Sugar: Generously sprinkle the additional 2 tablespoons of sugar over the top of the pineapple rings to create a caramelized crust during baking.
  9. Bake Cookies: Place the trays in the preheated oven and bake for 11-13 minutes, or until the edges of the cookies turn golden and the centers are set but still soft.
  10. Cool Cookies: Allow the cookies to cool on the baking tray for a few minutes to set, then transfer them carefully to a wire rack to cool completely before serving or storing.

Notes

  • Ensure pineapple rings are well-drained to prevent soggy cookies.
  • For a more pronounced vanilla flavor, use pure vanilla extract.
  • These cookies can be stored in an airtight container for up to 4 days at room temperature.
  • Use a gluten-free flour blend for a gluten-free version of this recipe.
  • Press the pineapple rings gently to avoid breaking the dough apart.
  • If you want a softer cookie, slightly underbake and allow to cool on the tray.

Keywords: pineapple, sugar cookies, upside down cookies, tropical dessert, easy cookie recipe, pineapple rings, baking