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Two Pineapple Upside-Down Cookies stacked, topped with pineapple rings and a cherry.

Pineapple Upside-Down Cookies

These cookies capture the classic pineapple upside-down cake flavors in a chewy cookie form.
Prep Time 20 minutes
Cook Time 12 minutes
Cooling Time 10 minutes
Total Time 42 minutes
Servings: 24 cookies
Course: Cookies, Dessert
Cuisine: American

Ingredients
  

For the Cookies
  • 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 soda
  • 0.5 teaspoon salt
For the Topping
  • 0.5 cup packed brown sugar
  • 0.25 cup unsalted butter melted
  • 0.25 cup crushed pineapple drained well
  • 0.25 cup maraschino cherries halved

Equipment

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

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.
  3. Beat in the eggs one at a time, then stir in the vanilla extract.
  4. In a separate bowl, whisk together the flour, baking soda, and salt.
  5. Gradually add the dry ingredients to the wet ingredients, mixing until just combined. Do not overmix.
  6. In a small bowl, combine the brown sugar and melted butter for the topping.
  7. Drop rounded tablespoons of cookie dough onto the prepared baking sheets, about 2 inches apart.
  8. Press a small amount of the brown sugar mixture onto the top of each cookie dough ball.
  9. Place a piece of maraschino cherry in the center of the brown sugar mixture on each cookie.
  10. Bake for 10-12 minutes, or until the edges are lightly golden brown.
  11. Let the cookies cool on the baking sheets for a few minutes before transferring them to a wire rack to cool completely.

Notes

You can add a pinch of cinnamon to the cookie dough for extra flavor. Ensure the pineapple is drained very well to prevent soggy cookies.