The moment I took a bite of these Pineapple Upside Sugar Cookies, I was transported back to summer picnics with my family, stealing the last slice of pineapple upside-down cake. This delightful cookie brings together the nostalgia of my childhood and the tropical sweetness of juicy pineapple, all nestled atop a buttery sugar cookie base. Perfect for beginners, this recipe is quick to whip up and guarantees smiles at any gathering. Plus, with a gluten-free option available, everyone can enjoy this sweet treat. Are you ready to add a splash of sunshine to your baking routine? Let’s dive into this easy, tropical cookie adventure!

Why Will You Love These Cookies?
Nostalgic Flavor: Each bite transports you back to summer picnics with its delightful combination of buttery sugar cookies and juicy pineapple.
Beginner-Friendly: This recipe is straightforward, making it perfect for novice bakers looking to impress family and friends.
Tropical Twist: Experience a sweet escape with a hint of the tropics, ideal for brightening up gatherings or casual snacking.
Gluten-Free Option: Enjoy worry-free indulgence with a simple 1:1 gluten-free flour swap.
Fast and Fresh: Ready in under 20 minutes, these cookies are perfect for last-minute summer events! Pair them with iced chai or pineapple iced tea for a refreshing treat.
Pineapple Upside Sugar Cookies Ingredients
• Through a delightful combination of flavors, enjoy creating the perfect Pineapple Upside Sugar Cookies!
For the Cookies
- Unsalted Butter – Provides a rich, creamy base; make sure it’s softened for easy mixing.
- Granulated Sugar – Adds sweetness while helping the cookies attain a light, fluffy texture.
- Egg – Serves as a binder to give structure and moisture to the dough.
- Vanilla Extract – Enhances flavor, bringing a warm aroma to each bite.
- All-Purpose Flour – The main component that forms the sturdy base of your cookies.
- Baking Soda – Acts as a leavening agent, adding lift and a slightly crispy edge.
- Salt – Balances sweetness and enhances the overall flavor profile.
For the Topping
- Canned Pineapple Rings – Canned adds juiciness and tropical flair; drain and dry thoroughly for best results. Fresh pineapple can be substituted, ensuring it’s well-dried.
- Additional Sugar for Sprinkling – This final touch adds sweetness and a sparkling finish to the caramelized pineapple topping.
Step‑by‑Step Instructions for Pineapple Upside Sugar Cookies
Step 1: Preheat the Oven
Preheat your oven to 350°F (175°C). While the oven warms up, line two baking sheets with parchment paper to prevent sticking and ensure even baking. The aroma of cookies baking in a warm oven is just around the corner!
Step 2: Cream Together the Butter and Sugar
In a large mixing bowl, combine softened unsalted butter and granulated sugar. Using an electric mixer, beat the mixture on medium speed until it becomes light and fluffy, about 3-4 minutes. This step is crucial for achieving the perfect texture in your Pineapple Upside Sugar Cookies.
Step 3: Add Wet Ingredients
Next, add in one egg and a splash of vanilla extract to the creamed mixture. Continue to mix on low speed until these wet ingredients are fully incorporated and the mixture appears smooth and silky, about 1-2 minutes. The vanilla will enhance the flavor, transporting you to summer kitchens past!
Step 4: Combine the Dry Ingredients
In a separate bowl, whisk together all-purpose flour, baking soda, and salt. Gradually add this dry mixture into the butter mixture, combining gently with a spatula or wooden spoon until a soft dough forms. Take care not to overmix, as we want soft cookies!
Step 5: Shape the Cookies
Using your hands, roll the dough into 1½ tablespoon balls. Gently flatten each ball into a disk and place them on the prepared baking sheets, leaving space between each for spreading. The cookies will puff up beautifully as they bake!
Step 6: Top with Pineapple
Take a canned pineapple ring (or a well-dried fresh one) and place it on top of each dough disk, pressing down slightly to secure it. For an extra touch of sweetness, sprinkle a little sugar on top of the pineapple rings, enchanting your Pineapple Upside Sugar Cookies with flavor.
Step 7: Bake the Cookies
Slide the baking sheets into the preheated oven and bake for 12–14 minutes. Keep an eye on them; the edges should become lightly golden, while the centers will remain soft and chewy. Your kitchen will soon fill with the irresistible scent of baking cookies!
Step 8: Cool Before Serving
Once baked, remove the cookies from the oven and let them cool on the sheets for 5 minutes. This will help them set. After cooling slightly, transfer the cookies to a wire rack to cool completely. They’re best served warm and fresh, with a tropical twist from the pineapple!

Storage Tips for Pineapple Upside Sugar Cookies
Room Temperature: Store cookies in an airtight container at room temperature for up to 3 days to maintain their softness and flavor.
Fridge: If you want them to last longer, place them in the fridge for up to a week. Just remember to allow them to reach room temperature before enjoying!
Freezer: Freeze cookies in layers separated by parchment paper, stored in a freezer-safe container for up to 2 months. Thaw at room temperature before serving for that fresh-baked taste.
Reheating: If you’d like to warm them up, simply pop them in the microwave for 10-15 seconds to revive their soft texture, perfect for your Pineapple Upside Sugar Cookies!
Pineapple Upside Sugar Cookies Variations
Feel free to get creative with these delightful Pineapple Upside Sugar Cookies, adding your unique touch for an even sweeter experience!
- Fresh Pineapple: Swap canned pineapple for fresh, ensuring it’s well-dried. This elevates the tropical freshness! A burst of natural sweetness takes these cookies to the next level.
- Cherry on Top: Add half a maraschino cherry on top of each pineapple ring for a fun retro twist, reminiscent of classic desserts. This vibrant addition brings a pop of color and flavor!
- Coconut Flour: Combine coconut flour with a gluten-free flour mix for a delightful tropical flair, embracing the coconut’s natural sweetness. This twist adds a lovely texture and flavor profile, perfect for a beach-themed gathering!
- Lime Zest: Add a teaspoon of fresh lime zest to the cookie dough for a zesty kick that perfectly complements the pineapple’s sweetness. Lime and pineapple—what a heavenly pairing!
- Dark Chocolate Drizzle: Finish the cookies with a dark chocolate drizzle for a luxurious touch that balances the sweetness and adds a sophisticated twist. It’s a flavor combination that will wow guests!
- Pineapple Coconut Icing: Top cookies with a light icing made from powdered sugar, coconut milk, and shredded coconut for an irresistible tropical finish. This adds creaminess and enhances the flavor.
- Spicy Kick: Sprinkle a pinch of cayenne pepper into the cookie dough for a subtle spicy undertone that contrasts beautifully with the sweet pineapple topping. For those who appreciate a bit of adventure in their baking!
- Sugar Substitute: Try substituting coconut sugar for granulated sugar for a richer flavor and a touch of natural caramel, bringing a slightly different sweetness to the cookie base.
No matter how you choose to customize these Pineapple Upside Sugar Cookies, your creativity will shine through! If you’re looking for more cookie ideas, check out my Brown Sugar Cookies or Pineapple Carrot Cream recipes to keep the deliciousness going! Happy baking!
Expert Tips for Pineapple Upside Sugar Cookies
- Dry Pineapple Thoroughly: Make sure your pineapple rings are well-drained and dried to prevent soggy cookies. This step keeps the texture just right.
- Use Parchment Paper: Lining your baking sheets with parchment paper prevents sticking and guarantees easy removal. Silicone baking mats work just as well!
- Don’t Overmix Dough: Mixing for too long can lead to tough cookies. Combine ingredients until just mixed to ensure a soft, chewy texture in your Pineapple Upside Sugar Cookies.
- Adjust Sugar If Needed: If you prefer a less sweet cookie, feel free to reduce sugar by 2-3 tablespoons without compromising the overall taste.
- Gluten-Free Option: Use a 1:1 gluten-free flour blend for a gluten-free version, ensuring everyone can enjoy these tropical delights!
What to Serve with Pineapple Upside Sugar Cookies
These delightful cookies are not just a treat on their own; they can transform your gatherings into a tropical paradise with the right pairings.
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Iced Chai: The spiced, creamy notes of iced chai complement the fruity sweetness of the cookies, creating a delightful flavor balance.
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Pineapple Iced Tea: This refreshing beverage echoes the tropical theme, offering a light and invigorating sip to savor alongside your sweet treats.
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Coconut Macarons: For an extra layer of tropical delight, serve these chewy coconut cookies that bring a blissful, nutty flavor contrast.
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Fresh Fruit Salad: A vibrant mix of seasonal fruits enhances the tropical theme while bringing fresh, juicy textures to the table—ideal for summer gatherings!
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Vanilla Ice Cream: Creamy vanilla ice cream melts beautifully over warm cookies, delivering a delightful contrast between temperatures and flavors.
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Chocolate Dipping Sauce: A rich chocolate drizzle adds a decadent touch, transforming your cookies into an indulgent dessert everyone will love.
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Pineapple Sorbet: For a light dessert option, this chilly treat echoes the pineapple flavor and provides a refreshing way to round out your meal.
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Mint Mojito: A crisp, refreshing drink with mint and lime slices will enhance any summer occasion, making it feel like a mini-vacation right at home.
Make Ahead Options
These Pineapple Upside Sugar Cookies are a fantastic choice for meal prep! You can prepare the cookie dough up to 24 hours in advance by mixing all your ingredients together and storing the dough in an airtight container in the refrigerator. To maintain their delightful texture, wrap the dough tightly to prevent it from drying out. Additionally, you can slice the drained pineapple rings and store them in the fridge for up to 3 days. When you’re ready to bake, simply scoop the chilled dough, top with the pineapple, and bake as instructed. This way, you’ll have fresh, delicious cookies with less fuss during busy weeknights or gatherings!

Pineapple Upside Sugar Cookies Recipe FAQs
How do I choose the right pineapple?
Absolutely! For the best flavor in your Pineapple Upside Sugar Cookies, select pineapple rings that are vibrant and juicy without dark spots all over. If using canned pineapple, look for brands with fruit packed in juice rather than syrup to keep the added sugar down.
How should I store the cookies?
You can keep your cookies in an airtight container at room temperature for up to 3 days. Alternatively, for longer storage, you can refrigerate them for about a week. Just remember to let them return to room temperature for that warm, fresh taste when serving!
Can I freeze these cookies?
Very! To freeze your Pineapple Upside Sugar Cookies, layer them between sheets of parchment paper within an airtight, freezer-safe container. This way, they won’t stick together. They can be frozen for up to 2 months. When you’re ready to enjoy, simply thaw them at room temperature for a delightful taste!
What should I do if my cookies come out too dry?
If your cookies end up a bit dry, there are some things you can try next time. Ensure you’re measuring ingredients accurately—too much flour can lead to dryness. Additionally, try to avoid overbaking; keep an eye on them and take them out as soon as the edges are golden while the centers remain soft.
Are these cookies safe for people with allergies?
Yes, but always check your ingredient labels! If you’re making these cookies for someone with allergies, you can substitute gluten-free flour to make them safe for those with gluten sensitivities. Ensure all other ingredients are also gluten-free, and be cautious with possible cross-contaminants, especially with shared kitchen equipment.
What if I don’t have parchment paper?
No worries if you don’t have parchment paper! You can grease your baking sheets well with butter or a non-stick cooking spray to prevent sticking. Alternatively, a silicone baking mat works beautifully if you have one on hand.

Pineapple Upside Sugar Cookies for a Sweet Tropical Escape
Ingredients
Equipment
Method
- Preheat your oven to 350°F (175°C) and line two baking sheets with parchment paper.
- In a large mixing bowl, cream together softened unsalted butter and granulated sugar until light and fluffy, about 3-4 minutes.
- Add in one egg and a splash of vanilla extract, mixing until fully incorporated.
- In a separate bowl, whisk together all-purpose flour, baking soda, and salt. Gradually add dry mixture into the butter mixture until a soft dough forms.
- Shape the dough into 1½ tablespoon balls, flattening them into disks on the prepared baking sheets.
- Place a canned pineapple ring on top of each disk, pressing down slightly, then sprinkle with sugar.
- Bake for 12-14 minutes until edges are lightly golden and centers remain soft.
- Cool on the sheets for 5 minutes, then transfer to a wire rack to cool completely.

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