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Pineapple Upside-Down Cookies with golden brown tops and a caramelized pineapple slice.

Pineapple Upside-Down Cookies

A delightful blend of chewy, buttery cookies topped with caramelized brown sugar, juicy pineapple, and a cherry, offering a tropical twist to your sweet tooth.
Prep Time 15 minutes
Cook Time 15 minutes
Total Time 30 minutes
Servings: 12 cookies
Course: Dessert, Snack
Cuisine: American, Tropical
Calories: 120

Ingredients
  

For the Cookie Dough
  • 1 cup crushed pineapple, drained
  • 1/2 cup brown sugar
  • 1/4 cup butter, softened
  • 1/2 teaspoon vanilla extract
  • 1 large egg
  • 1 1/2 cups all-purpose flour
  • 1 teaspoon baking powder
  • 1/4 teaspoon salt
For Topping
  • as needed Maraschino cherries for topping
  • as needed extra brown sugar for caramelized finish

Method
 

Preparation
  1. Preheat your oven to 350°F (175°C).
  2. In a large mixing bowl, cream together the softened butter and brown sugar until well combined.
  3. Add the egg and vanilla extract, mixing until smooth and fluffy.
  4. Fold in the drained crushed pineapple into the wet mixture.
  5. In a separate bowl, whisk together the all-purpose flour, baking powder, and salt.
  6. Gradually add the dry ingredients to the wet mixture, stirring gently until just combined.
  7. Using a tablespoon, scoop out portions of dough and place them on a parchment-lined baking sheet, leaving space for spreading.
  8. Press a Maraschino cherry into the center of each cookie, followed by a sprinkle of extra brown sugar on top.
Baking
  1. Place the cookies in the preheated oven and bake for 12-15 minutes or until the edges are lightly golden.
Cooling
  1. Allow the cookies to cool on the sheet for a few minutes before transferring them to a wire rack.

Notes

Store cookies in an airtight container at room temperature for up to 5 days. For longer storage, freeze for up to three months. To reheat, microwave for about 15-20 seconds or place in a preheated oven at 300°F (150°C) for a few minutes.