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Irresistible Pineapple Upside Down Sugar Cookies Recipe

4.5 from 129 reviews

Irresistible Pineapple Upside Down Sugar Cookies put a tropical twist on classic sugar cookies by topping them with caramelized pineapple and a maraschino cherry. These cookies combine a buttery, soft sugar cookie base with the sweet tang of pineapple and the rich flavor of brown sugar, baked to golden perfection. Perfect as a delightful dessert or a festive snack for any occasion.

Ingredients

Scale

For the Cookies:

  • 1 cup unsalted butter (softened)
  • 1 cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 2 1/2 cups all-purpose flour
  • 1 teaspoon baking soda
  • 1/2 teaspoon salt

For the Topping:

  • 1 can (20 oz) pineapple slices (drained)
  • 1/4 cup brown sugar
  • Maraschino cherries (for garnish)

Instructions

  1. Preheat the Oven: Preheat your oven to 350°F (175°C) and line baking sheets with parchment paper to prevent sticking and ensure even baking.
  2. Prepare the Cookie Dough: In a large mixing bowl, cream together the softened butter and granulated sugar until light and fluffy. Beat in the egg and vanilla extract until fully incorporated. In a separate bowl, whisk together the flour, baking soda, and salt. Gradually add the dry ingredients to the wet mixture, stirring until just combined to form the cookie dough.
  3. Prepare the Topping: Drain the pineapple slices and cut them into smaller pieces if desired. In a small bowl, combine the brown sugar with a small amount of pineapple juice from the can to create a sweet paste for drizzling.
  4. Assemble the Cookies: Using a cookie scoop or tablespoon, drop the cookie dough onto the prepared baking sheets, spacing each about 2 inches apart. Press a piece of pineapple into the center of each cookie, drizzle a small amount of the brown sugar mixture over the pineapple, and top each cookie with a maraschino cherry.
  5. Bake: Bake the cookies in the preheated oven for 12-15 minutes, or until the edges are lightly golden. Remove from oven and allow the cookies to cool on the baking sheets for a few minutes before transferring them to a wire rack to cool completely.
  6. Serve: Enjoy the pineapple upside down sugar cookies warm or at room temperature as a delicious dessert or snack.

Notes

  • You can add shredded coconut to the cookie dough for an extra tropical flavor.
  • Fresh pineapple can be used instead of canned for a fresher taste and texture.
  • Experiment with spices like cinnamon or nutmeg in the dough to enhance the flavor profile.
  • Ensure cookies cool completely to allow toppings to set without sliding off.
  • Store cookies in an airtight container at room temperature for up to 3 days for optimal freshness.

Keywords: Pineapple Upside Down Cookies, Sugar Cookies, Pineapple Cookies, Dessert Cookies, Tropical Cookies, Baked Cookies