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Delicious Pineapple Upside Down Cookie photo

Pineapple Upside Down Cookie

These Pineapple Upside Down Cookies are a tropical twist on a classic dessert, combining caramelized pineapple and cherries atop a soft, buttery cookie base.
Prep Time20 minutes
Cook Time15 minutes
Total Time35 minutes
Course: Dessert
Cuisine: American
Keyword: Cookie, Easy, Pineapple, Quick, Tropical
Servings: 24 servings

Ingredients

  • 1 cup unsalted butter softened
  • 1 cup granulated sugar
  • 2 large eggs
  • 1 cup all-purpose flour
  • 1 teaspoon baking powder
  • 1/2 teaspoon baking soda
  • 1/4 teaspoon salt
  • 1 teaspoon vanilla extract
  • 1 cup crushed pineapple drained
  • 1/2 cup brown sugar packed
  • maraschino cherries for topping

Instructions

  • Drain the crushed pineapple thoroughly. In a small bowl, mix the brown sugar with the pineapple, coating the fruit well. Set aside.
  • In a large mixing bowl, beat the softened unsalted butter and granulated sugar together using an electric mixer on medium speed until light and fluffy, about 3 to 4 minutes.
  • Add the eggs one at a time, beating well after each addition. Stir in the vanilla extract.
  • In a separate bowl, whisk together the all-purpose flour, baking powder, baking soda, and salt.
  • Gradually add the dry ingredients to the butter mixture, mixing on low speed until just combined. Avoid over-mixing.
  • Line a baking sheet with parchment paper or a silicone baking mat. Drop about a tablespoon of cookie dough onto the sheet, spacing about 2 inches apart. Flatten each mound slightly.
  • Spoon a small amount of the pineapple and brown sugar mixture onto each cookie, pressing gently into the dough. Place a maraschino cherry on top of each cookie.
  • Preheat oven to 350°F (175°C). Bake cookies for 12-15 minutes or until edges turn golden brown and the pineapple topping caramelizes.
  • Allow cookies to cool on the baking sheet for 5 minutes before transferring to a cooling rack. Serve warm or at room temperature.

Equipment

  • Mixing Bowls
  • Electric mixer or stand mixer
  • Measuring cups and spoons
  • Spatula
  • Baking sheet or cookie pan
  • Parchment paper or silicone baking mat
  • Cooling rack

Notes

  • Drain crushed pineapple thoroughly to avoid soggy cookies.
  • Avoid over-mixing dough once flour is added to keep cookies tender.
  • Try adding toasted coconut flakes for a tropical twist.
  • Cookies store well for 4 days at room temperature or can be frozen for longer storage.