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Close-up of Pineapple Upside-Down Cookies topped with pineapple and cherries on a white plate.

Pineapple Upside-Down Cookies

These cookies capture the classic pineapple upside-down cake flavors in a delightful cookie form. They feature a buttery cookie base topped with caramelized pineapple and a cherry.
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Prep Time 20 minutes
Cook Time 12 minutes
Cooling Time 10 minutes
Total Time 42 minutes
Servings: 24 cookies
Course: Dessert
Cuisine: American
Ingredients Equipment Method Notes

Ingredients
  

For the Cookie Dough
  • 1 cup unsalted butter softened
  • 1 cup granulated sugar
  • 2 large eggs
  • 1 teaspoon vanilla extract
  • 2.5 cups all-purpose flour
  • 1 teaspoon baking powder
  • 0.5 teaspoon salt
For the Topping
  • 1/2 cup packed brown sugar
  • 1/4 cup unsalted butter melted
  • 1 can (8 ounces) crushed pineapple well-drained
  • 24 maraschino cherries halved

Equipment

  • Baking sheets
  • Mixing bowls
  • Electric mixer
  • Measuring cups and spoons
  • Wire rack

Method
 

  1. Preheat your oven to 350°F (175°C). Line baking sheets with parchment paper.
  2. In a large bowl, cream together the softened butter and granulated sugar until light and fluffy. Beat in the eggs one at a time, then stir in the vanilla extract.
  3. In a separate bowl, whisk together the flour, baking powder, and salt. Gradually add the dry ingredients to the wet ingredients, mixing until just combined. Do not overmix.
  4. In a small bowl, combine the brown sugar and melted butter. Stir in the drained crushed pineapple.
  5. Drop rounded tablespoons of cookie dough onto the prepared baking sheets, about 2 inches apart.
  6. Spoon about 1 teaspoon of the pineapple mixture onto the center of each cookie dough ball. Press a cherry half into the center of the pineapple mixture.
  7. Bake for 10-12 minutes, or until the edges are lightly golden brown.
  8. Let the cookies cool on the baking sheets for a few minutes before transferring them to a wire rack to cool completely.

Notes

Store cooled cookies in an airtight container at room temperature for up to 3 days.