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Pineapple Upside-Down Cookies

Pineapple Upside-Down Cookies

5 from 18 reviews

Pineapple Upside-Down Cookies offer a delightful twist on the classic dessert by combining soft, buttery cookies with caramelized brown sugar, juicy pineapple pieces, and sweet maraschino cherries on top. These bite-sized treats are perfect as snacks, party favors, or a fun dessert to enjoy year-round.

Ingredients

Scale

For the Cookie Base:

  • ½ cup unsalted butter, softened
  • ¾ cup granulated sugar
  • 1 large egg
  • 1 tsp vanilla extract
  • 1 ¼ cups all-purpose flour
  • ½ tsp baking powder
  • ¼ tsp salt

For the Topping:

  • ½ cup brown sugar
  • 2 tbsp melted butter
  • 1 small can pineapple rings, cut into smaller pieces
  • Maraschino cherries, halved

Instructions

  1. Prepare the Cookie Dough: Preheat oven to 350°F (175°C) and line a baking sheet with parchment paper or a silicone mat. Cream softened butter and granulated sugar until light and fluffy using a mixer or whisk. Add egg and vanilla extract, mixing until smooth. In a separate bowl, whisk flour, baking powder, and salt. Gradually incorporate dry ingredients into the wet, mixing until a soft dough forms without overmixing.
  2. Prepare the Topping: In a small bowl, combine melted butter and brown sugar, stirring until smooth. Spoon about 1 teaspoon of this mixture onto the lined baking sheet, spacing them apart to allow room for spreading.
  3. Assemble the Cookies: Place a small piece of pineapple on each brown sugar base, then add a maraschino cherry half at the center. Scoop approximately 1 ½ tablespoons of cookie dough, flatten slightly, and cover the fruit and topping. Press edges gently to seal.
  4. Bake the Cookies: Bake for 12-15 minutes until edges are golden. Remove from oven and cool on the baking sheet for 5 minutes before transferring to a wire rack. Cooling helps the caramelized topping set properly.
  5. Serve and Enjoy: Once cooled completely, flip cookies upside-down to reveal the pineapple and cherry topping. Serve as a snack or dessert and enjoy the tropical, sweet flavors.

Notes

  • Use softened butter to ensure proper creaming and soft texture.
  • Substitute a flax egg for the egg to make the recipe vegan-friendly.
  • Use gluten-free flour blend if you need a gluten-free option.
  • Fresh pineapple can be used, but cut into small pieces for even baking.
  • Store cookies in an airtight container at room temperature for up to 3 days.
  • For a deeper caramel flavor, use brown sugar instead of white sugar in the cookie base if desired.

Nutrition

Keywords: pineapple upside-down cookies, pineapple cookies, caramelized cookies, tropical cookies, dessert cookies, party snacks