Go Back

Pineapple Upside-Down Cookies

These chewy cookies combine soft, buttery dough with sweet pineapple and cherries for a delightful twist on the classic pineapple upside-down cake.
Print Recipe Pin Recipe
Prep Time 15 minutes
Cook Time 15 minutes
Total Time 30 minutes
Servings: 24 cookies
Course: Dessert, Snack
Cuisine: American
Calories: 150
Ingredients Method Notes

Ingredients
  

Cookie Base
  • 1 cup unsalted butter, softened For best flavor
  • 1 cup brown sugar Packed
  • 2 large eggs Beaten
  • 2 teaspoons vanilla extract
Dry Ingredients
  • 2 cups all-purpose flour
  • 1 teaspoon baking powder
  • 1/2 teaspoon salt
Additions
  • 1 cup diced pineapple (drained) Fresh or well-drained canned
  • as needed Maraschino cherries for topping

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 smooth and fluffy.
  3. Beat in the eggs one at a time, mixing well after each addition, then stir in the vanilla extract.
  4. In a separate bowl, whisk together the all-purpose flour, baking powder, and salt.
  5. Gradually add the dry ingredients to the wet mixture, mixing until fully combined. Avoid overmixing.
  6. Fold in the drained diced pineapple gently with a spatula.
Baking
  1. Line a baking sheet with parchment paper.
  2. Drop spoonfuls of the cookie dough onto the prepared baking sheet, leaving space between each.
  3. Place a Maraschino cherry on top of each cookie.
  4. Bake for 12-15 minutes or until edges are golden brown.
  5. Allow cookies to cool on the baking sheet for a few minutes, then transfer to a wire rack to cool completely.

Notes

Store in an airtight container at room temperature for 3-5 days or freeze for up to 3 months. Use fresh pineapple for better flavor. Experiment with toppings like coconut, nuts, or chocolate chips.