Top-down view of Pineapple Upside Sugar Cookies on a white plate, each featuring a golden-brown sugar cookie base topped with a caramelized pineapple ring and a bright red maraschino cherry in the center.

Pineapple Upside Sugar Cookies Recipe: A Tropical Twist on a Classic Dessert

If you're a fan of pineapple upside-down cake, you're going to love these Pineapple Upside Sugar Cookies! These cookies are the perfect handheld version of the beloved classic dessert. Buttery sugar cookies topped with caramelized pineapple and a bright maraschino cherry combine to create a treat that’s as delightful to look at as it is to eat. Whether you’re hosting a gathering, looking for a fun baking project, or simply craving something sweet, these tropical cookies will transport your taste buds to paradise.

Why You’ll Love These Pineapple Upside Sugar Cookies

This recipe takes all the best parts of pineapple upside-down cake—the caramelized fruit topping, buttery flavor, and golden-brown perfection—and transforms them into a snackable cookie form. They’re easy to make, bursting with tropical flavor, and guaranteed to impress friends and family. Try these Pineapple Upside Sugar Cookies today!

Ingredients You’ll Need

For the Cookies:

  • 1 cup butter, room temperature 🧈
  • 1 ½ cups granulated sugar
  • 2 large eggs 🥚
  • 2 teaspoons vanilla extract
  • ½ cup sour cream
  • 3 cups all-purpose flour
  • 1 teaspoon baking powder
  • 1 teaspoon cornstarch
  • ½ teaspoon salt

For the Toppings:

  • 13 canned pineapple slices (drained) 🍍
  • 13 maraschino cherries 🍒
  • ½ cup melted butter 🧈
  • 1 cup packed light brown sugar

Step-by-Step Instructions

  1. In a large mixing bowl, cream together the butter and granulated sugar until light and fluffy.
  2. Add the eggs, one at a time, beating well after each addition. Mix in the vanilla extract and sour cream until smooth.
  3. In a separate bowl, whisk together the flour, baking powder, cornstarch, and salt.
  4. Gradually add the dry ingredients to the wet ingredients, mixing until a soft dough forms. Cover and chill the dough in the refrigerator for at least 30 minutes before making Pineapple Upside Sugar Cookies.

Step 2: Prepare the Pineapple Topping

  1. Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper.
  2. In a small bowl, combine the melted butter and brown sugar to create a caramel-like mixture.
  3. Arrange the pineapple slices on the prepared baking sheet. Spoon about 1 tablespoon of the caramel mixture over each pineapple slice and place a maraschino cherry in the center.

Step 3: Shape and Bake the Cookies

  1. Scoop out about 2 tablespoons of cookie dough and flatten it into a disc that matches the size of the pineapple slices.
  2. Place the dough discs on top of the prepared pineapple slices, pressing gently to adhere.
  3. Bake for 12-14 minutes, or until the edges of the cookies are lightly golden and the pineapple caramelizes into delicious Pineapple Upside Sugar Cookies.
  4. Let the cookies cool on the baking sheet for 5 minutes before carefully flipping them over to reveal the pineapple topping. Transfer to a wire rack to cool completely.

Tips for Perfect Pineapple Upside Sugar Cookies

  • Chill the Dough: Don’t skip chilling the dough! It helps the cookies hold their shape and ensures a perfect texture.
  • Use Parchment Paper: This prevents the caramelized pineapple topping from sticking to your baking sheet.
  • Flip Carefully: Use a spatula to flip the cookies gently after baking. They’ll be hot, so handle with care!

Serve and Enjoy!

These Pineapple Upside Sugar Cookies are perfect for summer parties, tropical-themed events, or anytime you want a burst of fruity flavor. Serve them as-is, or pair them with a scoop of vanilla ice cream for an extra indulgent treat.

Take a bite and let these cookies whisk you away to a sunny island escape—one delicious Pineapple Upside Sugar Cookies.

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