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A Fun Twist on a Classic Dessert Recipe

A Fun Twist on a Classic Dessert Recipe
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★★★★★

5 from 29 reviews

Pineapple Upside-Down Cookies combine the tropical sweetness of pineapple and maraschino cherries with a soft, buttery cookie base. This fun twist on the classic dessert features a caramelized brown sugar topping that creates a beautiful presentation and delightful flavor in every bite, perfect for snack time, parties, or a unique dessert.

Ingredients

Scale

Cookie Dough

  • 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

Topping & Assembly

  • 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 the oven to 350°F (175°C) and line a baking sheet with parchment paper or a silicone baking mat. In a mixing bowl, cream together the softened butter and granulated sugar until light and fluffy using a mixer or whisk. Add the egg and vanilla extract, mixing until smooth and glossy. In a separate bowl, whisk the flour, baking powder, and salt. Gradually add the dry ingredients to the wet mixture, stirring just until a soft dough forms. Avoid overmixing to keep the cookies tender.
  2. Prepare the Topping: In a small bowl, combine the melted butter and brown sugar 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 top of each brown sugar base. Add a halved maraschino cherry in the center of the pineapple. Scoop about 1 ½ tablespoons of cookie dough, flatten slightly, and place it gently over the fruit and topping, pressing the dough edges to seal.
  4. Bake the Cookies: Bake in the preheated oven for 12-15 minutes, or until cookies are golden around the edges. Remove and let cool on the baking sheet for 5 minutes before transferring to a wire rack. Cooling helps set the caramelized topping.
  5. Serve and Enjoy: Once completely cooled, flip the cookies upside-down to reveal the beautiful pineapple and cherry topping. Serve as a delightful snack, dessert, or party treat.

Notes

  • If using salted butter, reduce added salt to avoid excess saltiness.
  • For a deeper caramel flavor, substitute granulated sugar with brown sugar in the dough.
  • Egg allergy substitution: use a flax egg (1 tbsp ground flaxseed + 3 tbsp water) instead of 1 egg.
  • For gluten-free option, replace all-purpose flour with a 1:1 gluten-free flour blend.
  • Fresh pineapple can be used but cut into small tidbits for even cooking.
  • Alternatives to maraschino cherries include fresh cherries or dried cranberries.
  • Chilling dough briefly before baking can help reduce spreading if necessary.

Nutrition

Keywords: pineapple upside-down cookies, pineapple cookies, upside-down dessert, caramelized cookies, tropical cookies, maraschino cherry cookies

Find it online: https://nayabaker.com/a-fun-twist-on-a-classic-dessert-recipe/