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Irresistible Pineapple Upside-Down Cookies

These Pineapple Upside-Down Cookies bring a fun and delicious twist to the classic dessert! Soft, buttery cookies topped with caramelized pineapple and cherries make for a delightful treat.
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Equipment

  • Baking sheet
  • Parchment paper or silicone baking mat
  • Mixing bowls
  • Electric mixer or whisk
  • Measuring cups and spoons

Ingredients
  

  • For the Cookie Base:
  • 1/2 cup unsalted butter softened
  • 3/4 cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 1 1/4 cups all-purpose flour
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon salt
  • For the Topping:
  • 1/2 cup brown sugar
  • 2 tablespoons unsalted butter melted
  • 1 small can pineapple rings cut into smaller pieces or use pineapple tidbits
  • Maraschino cherries halved

Instructions
 

  • Prepare the Cookie Dough:
  • Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper or a silicone mat.
  • In a mixing bowl, cream together the softened butter and granulated sugar until light and fluffy.
  • Beat in the egg and vanilla extract until well combined.
  • In a separate bowl, whisk together the flour, baking powder, and salt. Gradually add the dry ingredients to the wet ingredients, mixing until a soft dough forms.
  • Prepare the Topping:
  • In a small bowl, combine the melted butter and brown sugar. Mix until smooth.
  • Spoon about 1 teaspoon of the brown sugar mixture onto the prepared baking sheet, spreading it slightly to form a base for each cookie.
  • Assemble the Cookies:
  • Place a small piece of pineapple (or pineapple tidbits) on top of the brown sugar mixture.
  • Add a maraschino cherry half in the center of the pineapple.
  • Scoop about 1 1/2 tablespoons of cookie dough and gently flatten it with your hands. Place the flattened dough over the pineapple and brown sugar, pressing lightly to cover.
  • Bake:
  • Bake in the preheated oven for 12-15 minutes, or until the cookies are golden around the edges.
  • Remove from the oven and let the cookies cool on the baking sheet for 5 minutes before carefully transferring them to a wire rack to cool completely.
  • Serve:
  • Once cooled, serve your Pineapple Upside-Down Cookies as a fun and delicious dessert or snack!