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Pineapple Upside Down Cookie

This Pineapple Upside Down Cookie is a tropical twist on a classic dessert! Sweet caramelized pineapple and cherries top a soft, buttery cookie that's perfect for any occasion.
Prep Time20 minutes
Cook Time15 minutes
Total Time35 minutes
Course: Dessert
Cuisine: American
Keyword: Cookie, Easy, Pineapple Upside Down, Quick, Tropical
Servings: 12 servings

Ingredients

Brown Sugar Topping

  • 1/2 cup brown sugar packed
  • 1/2 cup crushed pineapple drained

Cookie Dough

  • 1 cup unsalted butter softened
  • 1 cup granulated sugar
  • 2 large eggs
  • 1 tsp vanilla extract
  • 1 cup all-purpose flour
  • 1 tsp baking powder
  • 1/2 tsp baking soda
  • 1/4 tsp salt
  • maraschino cherries for garnish

Instructions

Preparation

  • Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper or a silicone baking mat to prevent sticking.

Make the Brown Sugar Topping

  • In a small bowl, combine the packed brown sugar with the drained crushed pineapple. Stir until well mixed to create a caramel-like topping.

Prepare the Cookie Dough

  • In a large bowl, use your mixer to cream 1 cup of softened unsalted butter with 1 cup of granulated sugar until light and fluffy, about 3-5 minutes on medium speed.
  • Beat in the 2 large eggs, one at a time, ensuring each is fully incorporated before adding the next. Mix in 1 teaspoon of vanilla extract.
  • In a separate bowl, whisk together 1 cup of all-purpose flour, 1 teaspoon baking powder, 1/2 teaspoon baking soda, and 1/4 teaspoon salt.
  • Gradually add the dry ingredients to the wet mixture, folding gently with a spatula or mixing on low speed. Stir just until combined.

Assemble and Bake

  • Drop spoonfuls of cookie dough onto the prepared baking sheet, spacing about 2 inches apart. Press a teaspoon of the pineapple and brown sugar mixture gently onto the top of each cookie. Top each with a maraschino cherry.
  • Bake the cookies for 12-15 minutes, until edges are lightly golden and tops are set. Watch carefully to avoid burning the brown sugar topping.
  • Allow cookies to cool on the baking sheet for 5 minutes before transferring to a cooling rack. Enjoy warm or at room temperature.

Equipment

  • Mixing Bowls
  • Electric mixer or hand mixer
  • Measuring cups and spoons
  • Spatula
  • Baking Sheet or Pan
  • Cooling rack

Notes

  • Make sure to drain the crushed pineapple thoroughly to prevent soggy cookies.
  • Avoid overmixing the dough to keep cookies tender and soft.
  • Watch the cookies closely during baking to prevent the brown sugar topping from burning.