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Pineapple Upside Down Cookie

This Pineapple Upside Down Cookie is a delightful tropical twist! Sweet, caramelized pineapple and cherry atop a tender buttery cookie—perfect for any occasion.
Prep Time15 minutes
Cook Time15 minutes
Total Time30 minutes
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

  • Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper or a silicone baking mat.
  • Drain the crushed pineapple well to avoid soggy cookies.
  • In a large mixing bowl, use an electric mixer to cream together the softened unsalted butter and granulated sugar until light and fluffy, about 3-4 minutes.
  • Add the eggs one at a time, mixing 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 mixture to the wet ingredients, mixing just until combined. Do not overmix.
  • Using a tablespoon or cookie scoop, drop dough balls onto the prepared baking sheet, leaving about 2 inches between each cookie.
  • Press a small spoonful of drained crushed pineapple gently onto the top of each cookie. Sprinkle about a teaspoon of packed brown sugar over the pineapple. Top each cookie with one maraschino cherry, pressing it lightly into the dough.
  • Bake the cookies for 12-15 minutes or until the edges are lightly golden and the tops are set, allowing the brown sugar to caramelize.
  • Allow the cookies to cool on the baking sheet for about 5 minutes before transferring to a wire rack to cool completely.

Equipment

  • Electric Mixer
  • Mixing Bowl
  • Baking Sheet
  • Parchment paper or silicone baking mat
  • Measuring cups and spoons
  • Spoon or cookie scoop
  • Wire Rack

Notes

  • Drain pineapple thoroughly to prevent soggy cookies.
  • Use room temperature butter and eggs for a better texture.
  • Broil cookies for 1-2 minutes at the end for extra caramelization, watching carefully.
  • Chill dough for 30 minutes for thicker cookies.
  • Add ground cinnamon or nutmeg to dry ingredients for a warm spice note.