Pineapple Upside Down Sugar Cookies

Pineapple upside down sugar cookies combine the classic flavors of pineapple upside-down cake with a soft, chewy cookie base. This delightful dessert captures the sweet and tangy essence of pineapple in each bite. These cookies are perfect for gatherings, parties, or simply satisfying your sweet tooth any time of day.

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Why You’ll Love This Pineapple Upside Down Sugar Cookies

This recipe combines the rich sweetness of sugar cookies with the tropical flavor of delicious pineapple. Each cookie features a bite of juicy pineapple, topped with a light sprinkle of sugar that adds a delightful caramelized finish. These cookies not only look stunning but also taste absolutely incredible. You will surely impress friends and family with this unique twist on a beloved classic.

How to Make Pineapple Upside Down Sugar Cookies

Ingredients:

  • 1 cup unsalted butter (softened)
  • 1 cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract (optional)
  • 2 cups all-purpose flour (or gluten-free blend)
  • 1 teaspoon baking soda
  • 1/2 teaspoon salt
  • 1 can canned pineapple rings (well-drained)
  • 2 tablespoons additional sugar for sprinkling

Step-by-Step Instructions:

  1. Preheat the Oven: Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper.
  2. Prepare the Pineapple: Drain the canned pineapple rings and pat them dry with a paper towel to remove excess moisture. Cut each ring into small pieces.
  3. Mix Butter and Sugar: In a large mixing bowl, cream together the softened butter and granulated sugar until light and fluffy.
  4. Add Egg and Vanilla: Beat in the egg and vanilla extract (if using) until well combined.
  5. Combine Dry Ingredients: In a separate bowl, whisk together the all-purpose flour, baking soda, and salt.
  6. Combine Mixtures: Gradually add the dry ingredients to the butter mixture, mixing until just combined. Be careful not to overmix.
  7. Fold in Pineapple: Gently fold in the small pieces of pineapple, ensuring even distribution within the dough.
  8. Scoop Cookies: Use a cookie scoop or tablespoon to drop dough onto the prepared baking sheet, leaving space between each cookie.
  9. Sprinkle with Sugar: Lightly sprinkle additional sugar on top of each cookie before baking.
  10. Bake: Bake for 10 to 12 minutes, or until the edges are lightly golden. Allow cookies to cool on the sheet for a few minutes before transferring to a wire rack to cool completely.

Pineapple Upside Down Sugar Cookies That Delight Every Bite

Pineapple Upside Down Sugar Cookies bring vibrant flavors and a touch of nostalgia in every bite. These soft, buttery cookies topped with sweet pineapple are perfect for parties, holidays, or anytime you want a cheerful dessert.
Prep Time 15 minutes
Cook Time 13 minutes
Total Time 38 minutes
Servings: 24 cookies
Course: Dessert
Cuisine: American
Calories: 150

Ingredients
  

Cookie Base
  • 1 cup unsalted butter softened
  • 1 cup granulated sugar
  • 1 egg large
  • 1 teaspoon vanilla extract optional
  • 2 cups all-purpose flour or gluten-free blend
  • 1 teaspoon baking soda
  • 1/2 teaspoon salt
Topping
  • 1 can pineapple rings well-drained
  • 2 tablespoons granulated sugar for sprinkling

Method
 

  1. Preheat your oven to 350°F (180°C) and line baking trays with parchment paper.
  2. Cream the softened butter and granulated sugar together until light and fluffy, about 2–3 minutes.
  3. Add the egg and vanilla extract, mixing well until fully combined.
  4. In a separate bowl, whisk together the flour, baking soda, and salt. Gradually add to the wet mixture until a soft dough forms.
  5. Scoop about 2 tablespoons of dough per cookie and place on the prepared trays, leaving space between each.
  6. Press a pineapple ring gently into each dough mound, flattening slightly, then sprinkle sugar over the top.
  7. Bake for 11–13 minutes, or until the edges are lightly golden and the centers are set.
  8. Allow cookies to cool on the tray for a few minutes, then transfer to a wire rack to cool completely.

Nutrition

Calories: 150kcalCarbohydrates: 22gProtein: 1gFat: 7gSaturated Fat: 4gCholesterol: 25mgSodium: 80mgPotassium: 50mgSugar: 10gVitamin A: 300IUVitamin C: 1mgCalcium: 10mgIron: 0.5mg

Notes

Pair these cookies with a scoop of vanilla bean ice cream for an extra indulgent dessert experience.

Tried this recipe?

Let us know how it was!

How to Serve Pineapple Upside Down Sugar Cookies

These cookies are a treat on their own or served with a dollop of whipped cream. For an extra special touch, consider drizzling with a simple glaze or serving with a side of fresh fruit. Pairing these cookies with a tropical drink or a refreshing lemonade adds to their appeal.

How to Store Pineapple Upside Down Sugar Cookies

To keep your cookies fresh, store them in an airtight container at room temperature for up to a week. For longer storage, consider freezing them. Place cooled cookies in a freezer-safe container layered with parchment paper and seal tightly. They can be frozen for up to three months. Just let them thaw at room temperature before enjoying.

Tips to Make Pineapple Upside Down Sugar Cookies Perfect

  • Use Room Temperature Ingredients: Ensure your butter is softened for easy mixing and better texture.
  • Don’t Skimp on Draining: Properly draining the pineapple prevents excess moisture, which can lead to soggy cookies.
  • Adjust Baking Time: Keep an eye on your cookies as every oven is different. Remove them when the edges are just golden.

Flavor Variations

Feel free to experiment with this recipe to suit your taste:

  • Coconut: Add desiccated coconut for a tropical twist.
  • Chopped Nuts: Incorporate chopped walnuts or pecans for added texture.
  • Spices: Add a pinch of cinnamon or nutmeg for warmth.

Pro Tips for Success

  • Don’t Overmix: Overmixing can lead to tough cookies. Mix until ingredients are just combined.
  • Chill the Dough: If your dough is too soft, chilling it for 30 minutes can help in shaping the cookies.
  • Watch the Sugar: Adjust the sugar topping according to your taste preference. A little less sugar still provides a great taste.

FAQs About Pineapple Upside Down Sugar Cookies

1. Can I use fresh pineapple instead of canned?

Yes, you can use fresh pineapple! Just make sure to finely chop it for even distribution in the cookie dough. Ensure it’s well-drained to avoid excess moisture.

2. Can I make these cookies gluten-free?

Absolutely! Substitute all-purpose flour with a gluten-free blend that measures cup-for-cup. Make sure the other ingredients, such as baking soda and sugar, are gluten-free.

3. How can I make the cookies chewier?

For chewier cookies, reduce the baking time slightly and add an extra tablespoon of butter. This keeps them soft and chewy even after cooling.

Final Thoughts

Pineapple upside down sugar cookies are an exciting twist on a classic dessert. Combining sweetness, tropical flavors, and a gorgeous presentation, they make for a delightful treat at any gathering. With easy-to-follow steps and simple ingredients, you can bake a batch that everyone will love. Enjoy every bite of these delicious cookies!

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