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Pineapple Upside Down Sugar Cookies: A Delicious Twist on a Classic Recipe

4.6 from 148 reviews

Pineapple Upside Down Sugar Cookies offer a delightful twist on the classic pineapple upside-down cake by combining the tropical sweetness of pineapple and cherries with soft, buttery sugar cookies. These charming treats are topped with caramelized brown sugar, pineapple rings, and maraschino cherries, creating a visually appealing dessert that’s perfect for any occasion.

Ingredients

Scale

Cookie Dough

  • 1 1/2 cups all-purpose flour
  • 3/4 cup granulated sugar
  • 1/2 cup unsalted butter, softened
  • 1 egg
  • 1 1/2 tsp baking powder
  • 1/4 tsp salt

Toppings

  • 6 canned pineapple rings
  • 1/2 cup brown sugar
  • 12 maraschino cherries (for garnish)

Instructions

  1. Preheat the oven: Set your oven to 350°F (175°C) and prepare a baking sheet by lining it with parchment paper to prevent sticking and make cleanup easier.
  2. Cream butter and sugar: In a mixing bowl, beat the softened unsalted butter and granulated sugar together until the mixture is light and fluffy, which helps create a tender cookie texture.
  3. Add the egg: Incorporate the egg into the butter and sugar mixture, mixing well to combine all ingredients evenly.
  4. Combine dry ingredients: In a separate bowl, whisk together the all-purpose flour, baking powder, and salt to evenly distribute the leavening agent and seasoning.
  5. Mix wet and dry ingredients: Gradually add the dry flour mixture to the wet ingredients, stirring until the dough is fully combined without overmixing, to keep the cookies tender.
  6. Prepare pineapple and sugar base: On the parchment-lined baking sheet, place a small spoonful of brown sugar in the center of each pineapple ring to create a caramelized base during baking.
  7. Add cherries: Place a maraschino cherry in the center of each pineapple ring atop the brown sugar for a burst of color and flavor.
  8. Shape and place dough: Scoop tablespoon-sized portions of cookie dough, flatten them slightly, and carefully place each portion on top of the pineapple rings.
  9. Bake cookies: Bake the assembled cookies in the preheated oven for 10-12 minutes, or until the edges are lightly golden brown and the cookies are cooked through.
  10. Cool the cookies: Let the cookies cool on the baking sheet for a few minutes to set before transferring them to a wire rack to cool completely, which helps maintain their shape and texture.
  11. Serve and enjoy: Serve the Pineapple Upside Down Sugar Cookies warm or at room temperature for the best taste experience.

Notes

  • Use canned pineapple rings drained well to avoid excess moisture in the cookies.
  • Softened butter at room temperature is key for proper creaming with sugar.
  • Flattening cookie dough slightly before baking ensures even cooking over the pineapple rings.
  • For a fun variation, experiment with adding a dash of cinnamon to the dry ingredients.
  • Store cookies in an airtight container at room temperature for up to 3 days to maintain freshness.

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