Go Back
A close-up shot of three pineapple upside down cookies stacked, showing the soft texture and the glistening caramelized pineapple topping.

Pineapple Upside Down Cookies: The Perfect Tropical Treat

This easy Pineapple Upside Down Cookies recipe creates soft, chewy cookies with a rich caramelized pineapple and cherry topping. It's a fun, tropical twist on the classic cake, perfect for any occasion and ready in just 35 minutes!
Print Recipe Pin Recipe
Prep Time 20 minutes
Cook Time 15 minutes
Total Time 35 minutes
Servings: 12 cookies
Course: Dessert, Snack
Cuisine: American
Calories: 210
Ingredients Equipment Method Notes

Ingredients
  

For the Topping
  • 1/4 cup unsalted butter melted
  • 1/2 cup packed light brown sugar
  • 12 canned pineapple rings drained and patted very dry
  • 12 maraschino cherries
For the Cookie Dough
  • 1 1/2 cups all-purpose flour
  • 1/2 tsp baking soda
  • 1/4 tsp salt
  • 1/2 cup unsalted butter softened to room temperature
  • 1/2 cup granulated sugar
  • 1 large egg room temperature
  • 1 tsp vanilla extract

Equipment

  • 1 12-cup muffin tin
  • 1 Electric mixer

Method
 

  1. Preheat oven to 350°F (175°C). Generously grease a standard 12-cup muffin tin.
  2. In a small bowl, mix melted butter and brown sugar. Spoon about 1 tbsp of the mixture into the bottom of each muffin cup. Place a pineapple ring on top, followed by a maraschino cherry in the center.
  3. In a medium bowl, whisk together flour, baking soda, and salt.
  4. In a large bowl, beat the softened butter and granulated sugar with an electric mixer until light and fluffy.
  5. Beat in the egg and vanilla extract until just combined.
  6. Gradually add the dry ingredients to the wet ingredients, mixing on low speed until a soft dough forms.
  7. Scoop the dough evenly over the pineapple in each muffin cup.
  8. Bake for 12-15 minutes, or until edges are golden brown.
  9. Let the pan cool for exactly 5 minutes before carefully inverting it onto a wire rack to release the cookies.

Notes

Pat Pineapple Dry: The most crucial step is to pat the pineapple rings very dry with a paper towel to prevent the cookies from becoming soggy.
Cooling Time: Do not let the cookies cool in the pan for more than 5 minutes, as the caramel will harden and make them difficult to remove.