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Filed Under: Dessert

Pineapple Upside Sugar Cookies: A Tropical Twist on Tradition

January 14, 2026 by chefkiwi Leave a Comment

Pineapple Upside Sugar Cookies

Welcome to the delightful world of Pineapple Upside Sugar Cookies, where classic flavors meet a fun twist that will have your taste buds dancing! Imagine the sweetness of a soft sugar cookie combined with the tropical freshness of pineapple, all nestled underneath a caramelized topping that’s simply irresistible. What makes these cookies special is not just their unique flavor combination, but the way they flip the traditional upside-down dessert on its head—literally!

As a cookie lover, I know how important it is to have a treat that stands out, and these cookies do just that. They’re perfect for any occasion, whether it’s a casual afternoon snack or a festive gathering. The chewy texture, paired with the juicy pineapple, creates a delightful contrast that keeps everyone coming back for more. Plus, they are incredibly easy to make, so you can whip up a batch in no time and impress your friends and family with something truly unique. Trust me, once you take that first bite, you’ll be hooked!

Pineapple Upside Sugar Cookies: A Tropical Twist on Tradition

Ingredient Notes

When making Pineapple Upside Sugar Cookies, it’s important to select the right ingredients to achieve that delicious tropical flavor and delightful texture. Here are the key ingredients you’ll need:

  • All-purpose flour: This forms the base of your cookies. You can substitute with gluten-free flour if you need a gluten-free option.
  • Granulated sugar: Essential for sweetness and texture. You may replace some with brown sugar for a deeper flavor.
  • Butter: Use unsalted butter for better control of salt in the recipe. If you prefer a dairy-free version, coconut oil works wonderfully.
  • Eggs: They bind the ingredients together. For an egg substitute, you can use unsweetened applesauce (1/4 cup for each egg).
  • Pineapple: Fresh pineapple is best for a bright flavor, but canned pineapple (in juice, not syrup) can also be used. Make sure to drain it well.
  • Baking powder: This helps the cookies rise, giving them a light texture. If you don’t have baking powder, you can make your own using baking soda and cream of tartar.
  • Vanilla extract: This adds depth of flavor. You can use almond extract for a different twist.
  • Salt: A pinch enhances all the flavors; there’s no substitute needed here.

Step-by-Step Instructions

Let’s dive into the fun part—baking these scrumptious Pineapple Upside Sugar Cookies!

  1. Preheat your oven: Start by preheating your oven to 350°F (175°C). This ensures your cookies bake evenly.
  2. Prepare the baking sheet: Line a baking sheet with parchment paper. This prevents sticking and allows for easy cleanup.
  3. Cream the butter and sugar: In a large mixing bowl, beat together 1 cup of softened unsalted butter and 1 cup of granulated sugar until light and fluffy, about 3-5 minutes.
  4. Add eggs and vanilla: Mix in 2 large eggs, one at a time, followed by 1 teaspoon of vanilla extract. Make sure everything is well combined.
  5. Combine dry ingredients: In a separate bowl, whisk together 2 cups of all-purpose flour, 1 teaspoon of baking powder, and a pinch of salt.
  6. Mix dry with wet: Gradually add the dry mixture to the wet mixture, stirring until just combined. Be careful not to overmix!
  7. Fold in the pineapple: Gently fold in 1 cup of finely chopped pineapple. This will add moisture and sweetness to your cookies.
  8. Scoop the dough: Using a cookie scoop or tablespoon, drop rounded balls of dough onto the prepared baking sheet, leaving some space between them.
  9. Bake: Bake in the preheated oven for 12-15 minutes, or until the edges are lightly golden. The centers might look a little underbaked; that’s okay, they’ll continue to cook on the sheet.
  10. Cool down: Allow the cookies to cool on the baking sheet for about 5 minutes before transferring them to a wire rack to cool completely.

Tips & Suggestions

Here are some helpful tips to ensure your Pineapple Upside Sugar Cookies turn out perfectly:

  • Chill the dough: If you find the dough too sticky, chill it in the refrigerator for about 30 minutes before scooping. This will make it easier to handle.
  • Experiment with toppings: Consider adding shredded coconut or chopped macadamia nuts for extra texture and flavor.
  • Check for doneness: Keep an eye on your cookies as they bake. Oven temperatures can vary, so adjust baking time as needed.
  • Presentation: For a fun twist, you can drizzle melted white chocolate over the cooled cookies for a tropical touch.

Storage

To keep your Pineapple Upside Sugar Cookies fresh and delicious:

  • Room temperature: Store cooled cookies in an airtight container at room temperature for up to 5 days.
  • Refrigeration: If you want to keep them longer, place them in the refrigerator for up to 2 weeks. Just be sure to separate layers with parchment paper to avoid sticking.
  • Freezing: You can freeze the cookie dough for up to 3 months. Scoop the dough onto a baking sheet, freeze until firm, then transfer to a zip-top bag. When ready to bake, bake directly from frozen, adding a couple of extra minutes to the baking time.

Enjoy baking and indulging in these delightful Pineapple Upside Sugar Cookies! They are sure to bring a sweet tropical vibe to any occasion.

Pineapple Upside Sugar Cookies: A Tropical Twist on Tradition

Final Thoughts

If you’re looking for a delightful twist on traditional cookies, then the Pineapple Upside Sugar Cookies are a must-try! These cookies combine the sweet, tropical flavor of pineapple with the classic buttery goodness of sugar cookies, creating a treat that’s both refreshing and comforting. I absolutely love how the vibrant pineapple topping adds a splash of color and fun to each bite, making them perfect for any occasion, from casual get-togethers to festive celebrations. Plus, they are surprisingly easy to make, allowing you to impress your friends and family without spending hours in the kitchen. So go ahead, whip up a batch of Pineapple Upside Sugar Cookies, and let the delightful flavors transport you to a sunny paradise. You won’t regret it!

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