As I sifted through my pantry on a lazy summer afternoon, a delightful idea struck me: why not combine the tropical sweetness of pineapple with classic sugar cookies? This spark led me to create Pineapple Upside Sugar Cookies, a playful twist on a beloved treat. These cookies are not only a beautiful addition to any summer gathering but are also incredibly easy to make, even for beginner bakers. What’s more, the pillowy texture coupled with caramelized pineapple on top makes them a guaranteed crowd-pleaser. Perfect for indulging your sweet tooth or impressing guests at your next barbecue, this cheerful recipe will transport you to sunny shores with every bite. Curious about how to bring this tropical delight into your kitchen? Let’s dive into the delicious details!

Why are Pineapple Upside Sugar Cookies a Must-Try?
Delightful Flavor: These cookies unite sweet buttery dough with juicy pineapple, creating a tropical explosion of taste that’s simply irresistible.
Beginner-Friendly: Perfect for novice bakers, this recipe is easy to follow, ensuring success with minimal fuss.
Impressive Presentation: The caramelized pineapple on top offers a stunning visual appeal, making them a hit at any gathering.
Versatile Treat: Enjoy these cookies as snacks or dessert, and consider serving them alongside iced chai or a fresh pineapple iced tea for added flair.
Gluten-Free Option: With a simple swap, you can make these cookies accessible for those with dietary restrictions.
Crowd-Pleaser: Their unique flavor and fun twist on a classic means everyone will be reaching for more!
Pineapple Upside Sugar Cookies Ingredients
• The perfect components for these tropical treats await you!
For the Dough
- Unsalted Butter – Provides richness and moisture; use softened butter for better incorporation.
- Granulated Sugar – Adds sweetness and contributes to the cookie’s structure; can reduce by 2–3 tablespoons if desired.
- Egg – Binds the ingredients and helps leaven the cookies; essential for a good texture.
- Vanilla Extract – Enhances flavor; opt for pure vanilla for the best results.
- All-Purpose Flour – The main structure component; can be replaced with a gluten-free 1:1 baking blend.
- Baking Soda – Acts as a leavening agent, helping cookies rise.
- Salt – Balances sweetness and enhances flavor.
For the Topping
- Canned Pineapple Rings – The signature topping; must be well-drained and dried, or use fresh pineapple, patted dry.
- Additional Sugar for Sprinkling – Adds a sweet finishing touch; optional for extra sweetness.
Step‑by‑Step Instructions for Pineapple Upside Sugar Cookies
Step 1: Preheat the Oven
Begin by preheating your oven to 350°F (175°C). While the oven warms up, line your baking sheets with parchment paper, providing a non-stick surface for your cookies. This step is crucial to ensure the Pineapple Upside Sugar Cookies bake evenly and don’t stick, making for an easy release once they cool.
Step 2: Cream the Butter and Sugar
In a large mixing bowl, combine softened unsalted butter and granulated sugar. Using a hand mixer or stand mixer, beat the mixture on medium speed for about 3–5 minutes until it becomes light and fluffy. You’ll know it’s ready when the color lightens and the texture resembles a creamy cloud, enhancing the cookie’s richness.
Step 3: Add Egg and Vanilla
Next, crack in one egg and pour in the vanilla extract to the creamed butter and sugar mixture. Beat everything together until fully combined, which should take about 1–2 minutes. This step adds moisture and a lovely aroma, making your Pineapple Upside Sugar Cookies even more enticing.
Step 4: Combine Dry Ingredients
In a separate bowl, whisk together all-purpose flour, baking soda, and salt. Gradually incorporate the dry mixture into the wet ingredients, stirring continuously until a soft dough forms. This should take about 2 minutes, and your dough will be soft, slightly sticky, and ready for shaping.
Step 5: Shape the Dough
Take small amounts of dough and roll them into balls, approximately 1½ tablespoons each. Flatten each ball slightly to form a disk shape. Place these cookie disks on the prepared baking sheets with enough space between each for the cookies to spread. This ensures your Pineapple Upside Sugar Cookies have room to breathe while baking.
Step 6: Add the Pineapple Topping
Now for the fun part! Take drained and dried canned pineapple rings, and place one on top of each cookie disk, pressing down gently. If you like a hint of extra sweetness, sprinkle a little additional sugar on top of each pineapple ring. This will caramelize beautifully, adding a delicious finish.
Step 7: Bake and Cool
It’s time to bake! Place the baking sheets into your preheated oven and bake for 12–14 minutes. Keep an eye on them; the cookies are ready when the edges turn golden and the centers look set but still soft. Remove them from the oven and let cool on the baking sheets for 5 minutes.
Step 8: Transfer and Serve
After cooling, carefully transfer the cookies to a wire rack to cool completely. This final step ensures the cookies maintain their soft, pillowy texture, accentuated by the caramelized pineapple. Once cool, they’re ready to be enjoyed or served at your next gathering, offering a delightful taste of summer!

Pineapple Upside Sugar Cookies Variations
Feel free to play around with these ideas to make your Pineapple Upside Sugar Cookies your own special creation!
-
Fresh Pineapple: Use fresh pineapple for a brighter, juicier topping. Just ensure to blot it dry to avoid excess moisture.
-
White Chocolate Dip: Dunk your cookies in melted white chocolate for a delightful twist that adds richness and sweetness.
-
Brown Sugar: Substitute half of the granulated sugar with brown sugar for a deeper, caramel-like flavor that contrasts beautifully with the pineapple.
-
Coconut Flakes: Mix in shredded coconut into the dough for a tropical flair that will transport you right to a sunlit beach.
-
Spiced Version: Add a dash of cinnamon or nutmeg for a warm, spiced take that balances the sweetness of the pineapple.
-
Nutty Crunch: Fold in chopped macadamia nuts to bring a delightful crunch and nutty flavor that pairs perfectly with the tropical theme.
-
Heat It Up: Incorporate a pinch of cayenne or chili powder to the sugar topping for a surprising hint of heat that elevates each bite.
-
Gluten-Free: Use a gluten-free 1:1 baking blend in place of all-purpose flour to cater to those with dietary restrictions without sacrificing taste.
By mixing and matching these variations, you’ll make your Pineapple Upside Sugar Cookies shine in different ways—each time a new adventure awaits! And for an extra treat, pair these cookies with a refreshing iced chai or a glass of pineapple iced tea for a delightful summer experience.
Make Ahead Options
These Pineapple Upside Sugar Cookies are perfect for busy home cooks looking to save time without sacrificing flavor! You can prepare the cookie dough up to 24 hours in advance; simply wrap it tightly in plastic wrap and refrigerate it. Additionally, you can top the dough with pineapple rings (after ensuring they are well-drained and dried) and then cover the baking sheet with plastic wrap and refrigerate for no more than 3 hours before baking. When you’re ready to enjoy your delicious cookies, simply bake them directly from the fridge, adding a minute or two to the baking time if necessary. This way, you can ensure that these delightful treats remain just as soft and tropical-tasting as if you’d made them fresh, making them a stress-free dessert option for any occasion!
What to Serve with Pineapple Upside Sugar Cookies
Indulging in these tropical delights is just the beginning—let’s create a full experience for your taste buds!
-
Iced Chai: This spiced drink brings a warm flavor contrast, balancing the sweetness of the cookies beautifully.
-
Pineapple Iced Tea: Refreshing and fruity, this drink mirrors the cookie’s main ingredient, enhancing the tropical vibe at any gathering.
-
Lemon Bars: Their tangy zest complements the sweetness of the cookies, offering a delightful contrast that every dessert plate needs.
-
Coconut Macaroons: Chewy and nutty, these treats add texture and echo the tropical flair of your cookies, creating a harmonious dessert theme.
-
Berry Salad: A mix of fresh berries adds a refreshing and vibrant element, perfectly cutting through the richness of the sugar cookies.
-
Whipped Cream: A dollop on the side enhances the cookies’ soft texture and creamy sweetness, perfect for a decadent finish.
-
Vanilla Ice Cream: Serve these cookies warm, topped with a scoop of vanilla ice cream, creating a melt-in-your-mouth experience that’s simply unforgettable.
-
Sparkling Water: Citrus-flavored sparkling water aids digestion and refreshes the palate, making it a great non-alcoholic beverage choice.
Expert Tips for Pineapple Upside Sugar Cookies
-
Dough Consistency: Keep the dough slightly sticky; this helps achieve that melt-in-your-mouth texture. Avoid adding too much extra flour.
-
Pineapple Prep: Make sure to dry the pineapple rings thoroughly to prevent excess moisture, which can lead to soggy cookies.
-
Baking Sheets: Use parchment paper or silicone baking mats for easy release and even baking of your Pineapple Upside Sugar Cookies.
-
Cooling Time: Allow the cookies to cool on the baking sheet for a few minutes before transferring them to a wire rack. This helps them set properly.
-
Storage Tips: Store cookies in an airtight container for up to a week, or freeze them for later enjoyment to keep them fresh!
How to Store and Freeze Pineapple Upside Sugar Cookies
Room Temperature: Store cookies in an airtight container for up to 5 days to maintain freshness and texture.
Fridge: If you prefer chilled cookies, keep them in the refrigerator for up to 1 week, ensuring they’re in a sealed container to prevent drying out.
Freezer: Freeze cookies individually between layers of parchment paper for up to 3 months. Thaw at room temperature before serving to enjoy the delightful flavors of your Pineapple Upside Sugar Cookies.
Reheating: To refresh frozen cookies, warm them in the oven at 300°F (150°C) for 5-10 minutes. This will restore their soft, pillowy texture!

Pineapple Upside Sugar Cookies Recipe FAQs
What type of pineapple should I use for these cookies?
I recommend using canned pineapple rings as they are conveniently pre-sliced and juicy. Ensure they are well-drained and patted dry to avoid excess moisture that can make the cookies soggy. Fresh pineapple can be used too, but remember to slice it, then thoroughly blot dry to mimic the texture of canned pineapple.
How should I store Pineapple Upside Sugar Cookies?
Store your Pineapple Upside Sugar Cookies in an airtight container at room temperature for up to 5 days. If you want a chilled treat, refrigerate them for up to a week, keeping them sealed to prevent drying out.
Can I freeze Pineapple Upside Sugar Cookies?
Absolutely! To freeze your cookies, first, let them cool completely. Then, layer them between pieces of parchment paper in an airtight container or freezer bag. They can be stored in the freezer for up to 3 months. To enjoy, simply thaw them at room temperature, or warm them in the oven at 300°F (150°C) for about 5-10 minutes to regain their delightful softness.
What if my cookies turn out too soggy?
If your Pineapple Upside Sugar Cookies are soggy, it’s likely due to excess moisture from the pineapple. Always ensure the rings are well-drained and dried before placing them on the cookies. Another tip is to bake them a little longer, checking for a golden edge—just be careful not to overbake, as they can dry out.
Are these cookies suitable for gluten-free diets?
Yes, you can easily make these Pineapple Upside Sugar Cookies gluten-free! Simply substitute the all-purpose flour with a 1:1 gluten-free baking blend. This keeps the recipe accessible to those with dietary restrictions while maintaining that delicious buttery sweetness we all love.
Can I make other variations of this recipe?
Of course! You can switch it up by using fresh pineapple instead of canned. Consider adding shredded coconut into the dough for an extra tropical touch or even drizzling white chocolate over the cooled cookies for a decadent twist. The possibilities are as plentiful as the flavors!

Pineapple Upside Sugar Cookies: Tropical Treats for All
Ingredients
Equipment
Method
- Preheat your oven to 350°F (175°C) and line your baking sheets with parchment paper.
- In a large mixing bowl, cream together softened butter and granulated sugar until light and fluffy.
- Add the egg and vanilla extract, beating until fully combined.
- In a separate bowl, whisk together flour, baking soda, and salt, then mix into the wet ingredients until a soft dough forms.
- Roll the dough into balls, flatten them slightly, and place on the prepared baking sheets.
- Place a pineapple ring on top of each cookie and sprinkle with additional sugar if desired.
- Bake for 12-14 minutes or until edges are golden, then cool on sheets for 5 minutes before transferring to a wire rack.
- Enjoy your cookies once they have cooled completely!

Leave a Reply