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Pineapple Upside Down Cookie

This Pineapple Upside Down Cookie is a delightful, portable twist on the classic cake—soft, buttery cookies topped with caramelized pineapple and cherries!
Prep Time15 minutes
Cook Time15 minutes
Total Time30 minutes
Course: Dessert
Cuisine: American
Keyword: Baking, Cookie, Easy, Pineapple, Snack
Servings: 24 servings

Ingredients

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

Instructions

  • Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper or a silicone baking mat to prevent sticking and ensure even baking.
  • In a large bowl, beat together 1 cup of softened unsalted butter and 1 cup granulated sugar until light and fluffy, about 3-4 minutes using an electric mixer on medium speed.
  • Add 2 large eggs, one at a time, beating well after each addition. Stir in 1 teaspoon vanilla extract until combined.
  • In a separate bowl, whisk together 1 cup all-purpose flour, 1 teaspoon baking powder, 1/2 teaspoon baking soda, and 1/4 teaspoon salt.
  • Gradually add the dry ingredients into the wet mixture, mixing on low speed until just combined. Be careful not to overmix to keep the cookies tender.
  • In a small bowl, mix 1/2 cup packed brown sugar with 1 cup drained crushed pineapple. This mixture will give the cookies their signature caramelized pineapple topping.
  • Using a tablespoon or cookie scoop, drop cookie dough rounds onto the prepared baking sheet. Gently press about a teaspoon of the pineapple and brown sugar mixture onto the top of each dough ball. Place a maraschino cherry on top of each mound for that classic look.
  • Bake in the preheated oven for 12-15 minutes, or until the edges are golden and the cookie tops have caramelized slightly. The pineapple topping will bubble and look sticky—this is exactly what you want.
  • Allow the cookies to cool on the baking sheet for 5 minutes before transferring them to a cooling rack to cool completely. This helps the topping set and prevents it from sliding off.

Equipment

  • Mixing Bowls
  • Electric mixer or stand mixer
  • Measuring cups and spoons
  • Baking Sheet
  • Parchment paper or silicone baking mat
  • Cooling rack

Notes

  • Ensure pineapple is well drained to avoid soggy cookies.
  • Press the topping gently into the dough to keep it from spreading too much during baking.
  • Cookies freeze well; thaw at room temperature before serving.