Pineapple Upside Sugar Cookies: A Tropical Twist on a Classic Favorite
If you love the sunny flavor of pineapple and the buttery simplicity of sugar cookies, you’re in for a treat. These Pineapple Upside Sugar Cookies combine two nostalgic desserts—pineapple upside-down cake and classic sugar cookies—into one sweet, fruity, and chewy bite-sized indulgence.
Perfect for summer gatherings, holiday trays, or just when you’re craving something tropical, these cookies are easy to make and hard to resist. Let’s dive in!
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Why You’ll Love These Pineapple Sugar Cookies
This recipe brings together the soft texture of homemade sugar cookies with the bright, juicy flavor of pineapple. The pineapple rings caramelize slightly in the oven, creating a golden, glossy top that looks just as good as it tastes.
What Makes These Cookies Special:
Easy, beginner-friendly dough
Sweet and tangy pineapple topping
No fancy tools or mixers needed
Kid-approved and freezer-friendly
Unique twist that stands out on any cookie platter
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Ingredients You’ll Need
Here’s what you need to whip up a batch of pineapple upside-down cookies at home:
1 cup unsalted butter, softened
1 cup granulated sugar
1 egg
1 teaspoon vanilla extract
2½ cups all-purpose flour
½ teaspoon baking soda
¼ teaspoon salt
10–12 canned pineapple rings, well-drained and patted dry
Additional sugar, for sprinkling on top
> 🍍 Tip: Blot the pineapple rings thoroughly with paper towels—dry fruit helps the cookies bake evenly and prevents sogginess.
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How to Make Pineapple Upside Sugar Cookies
Step 1: Prepare the Dough
In a large mixing bowl, cream together the softened butter and sugar until light and fluffy. Add the egg and vanilla extract, mixing until well combined.
In a separate bowl, whisk together the flour, baking soda, and salt. Gradually add the dry ingredients to the wet mixture, stirring just until a soft dough forms. Chill the dough for 30 minutes to make it easier to work with.
Step 2: Preheat & Prep
Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper. Cut the pineapple rings in half (or smaller if needed) to better fit the size of the cookies.
Step 3: Shape and Assemble
Scoop out about 1½ tablespoons of dough and roll into balls. Place on the baking sheet with space in between. Gently flatten each dough ball and press a piece of pineapple into the center. Sprinkle the tops with a little extra sugar for a hint of sparkle and crunch.
Step 4: Bake to Perfection
Bake for 12–15 minutes, or until the edges are lightly golden and the pineapple is caramelized. Let the cookies cool on the pan for 5 minutes before transferring to a wire rack.
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Tips & Variations
Use maraschino cherries: Place one in the center of each pineapple ring for that retro upside-down cake look.
Make mini versions: Use pineapple tidbits instead of rings for bite-sized treats.
Try brown sugar: Sprinkle brown sugar instead of white for deeper caramel flavor.
Add coconut: Mix shredded coconut into the dough for extra island vibes.
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Storing & Serving Suggestions
Store the cooled cookies in an airtight container at room temperature for up to 3 days, or in the refrigerator for up to 5 days. For longer storage, freeze them (without pineapple topping) and add fruit fresh before baking or serving.
Serve with a glass of cold milk, a scoop of vanilla ice cream, or just on their own—they’re that good!
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Final Thoughts
These pineapple upside sugar cookies are a delightful twist on two beloved desserts. They’re tropical, tender, and totally unexpected in the best way. Whether you’re baking for a crowd or indulging solo, this recipe will brighten your day with every bite.
> 📌 Pin, save, or share this recipe now—because once you taste them, you’ll want to make them again and again!
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