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Pineapple Upside Down Sugar Cookies with a cherry topping on a plate

Pineapple Upside Down Sugar Cookies

Quick, easy, and delicious, these cookies are a delightful twist on a classic dessert, featuring soft, chewy cookies topped with caramelized pineapple and a cherry.
Prep Time 30 minutes
Cook Time 12 minutes
Total Time 42 minutes
Course Dessert, Snack
Cuisine American
Servings 24 cookies
Calories 150 kcal

Ingredients
  

Cookie Base

  • 1 cup unsalted butter, softened
  • 1 cup granulated sugar
  • 1 cup brown sugar, packed
  • 2 large eggs
  • 1 teaspoon vanilla extract
  • 4 cups all-purpose flour
  • 1 teaspoon baking powder
  • 1/2 teaspoon baking soda
  • 1/4 teaspoon salt

Topping

  • 1 cup crushed pineapple, drained
  • as needed maraschino cherries for garnishing

Instructions
 

Preparation

  • Preheat the oven to 350°F (175°C).
  • In a large bowl, cream together the softened butter, granulated sugar, and brown sugar until smooth and fluffy (about 3-5 minutes).
  • Beat in the eggs one at a time, then stir in the vanilla extract.
  • In a separate bowl, whisk together the flour, baking powder, baking soda, and salt. Gradually add to the butter-sugar mixture until just combined.
  • Gently fold in the crushed pineapple into the cookie dough.

Baking

  • Scoop tablespoon-sized balls of dough onto a lined baking sheet.
  • Place a maraschino cherry in the center of each cookie. Optionally, sprinkle a little brown sugar over each cookie before baking.
  • Bake for about 10-12 minutes or until the edges are golden brown.
  • Let cool on the baking sheet for a few minutes before transferring to a wire rack.

Notes

Chill the dough for about 30 minutes to help the cookies hold their shape better. You can try other fruits for different flavors, and if kids resist pineapple, consider adding shredded coconut or finely chopped nuts.
Keyword Cookie Swap, Dessert Recipe, Pineapple Upside Down Cookies, Quick Treat, Sugar Cookies