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Pineapple Upside Down Cookies on a plate with pineapple slices and cherries

Pineapple Upside Down Sugar Cookies

Mira
Delightful sugar cookies topped with caramelized pineapple, capturing the classic flavors of pineapple upside down cake in a handheld treat.
Prep Time 20 minutes
Cook Time 12 minutes
Total Time 32 minutes
Course Dessert, Snack
Cuisine American
Servings 24 cookies
Calories 150 kcal

Ingredients
  

For the Topping

  • 1 cup pineapple chunks (fresh or canned) Fresh pineapple adds brightness and flavor.
  • 1/2 cup brown sugar
  • 1/4 cup unsalted butter Melted for topping.

For the Cookie Dough

  • 1 cup granulated sugar
  • 1/2 cup unsalted butter, softened Bring to room temperature for best results.
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 2 cups all-purpose flour
  • 1 teaspoon baking soda
  • 1/2 teaspoon salt
  • optional maraschino cherries for garnish For classic touch.

Instructions
 

Prepare the Topping

  • Preheat your oven to 350°F (175°C).
  • In a saucepan over medium heat, melt the butter for the topping. Stir in the brown sugar until dissolved.
  • Add the pineapple chunks and cook for 2-3 minutes until heated through. Remove from heat.

Make the Cookie Dough

  • In a large mixing bowl, cream together the softened butter and granulated sugar until light and fluffy.
  • Add in the egg and vanilla extract, beating well to combine.
  • In another bowl, combine the flour, baking soda, and salt. Gradually add this to the wet mixture, mixing until just combined.

Assemble the Cookies

  • Line a baking sheet with parchment paper.
  • Place a spoonful of the pineapple topping in the center of each cookie, then add about 1-2 tablespoons of cookie dough on top. Press gently to mold the dough around the pineapple.
  • Optionally, place a maraschino cherry on top of each cookie for a classic touch.

Bake

  • Bake for 10-12 minutes or until the edges are lightly golden.
  • Let them cool on the baking sheet for a few minutes before transferring to a wire rack to cool completely.

Notes

For the best results, let your butter come to room temperature before creaming with sugar. Avoid overmixing the dough to keep cookies tender.
Keyword Baking, Pineapple Cookies, Pineapple Upside Down Cookies, Sugar Cookies, Tropical Cookies