The scent of summer spun its way through my kitchen as I baked my latest treat, and I couldn’t help but smile. These Pineapple Upside Sugar Cookies whip together the perfect harmony of soft, buttery sugar cookies and bright, juicy pineapple rings, making each bite feel like a mini vacation. Not only are they a breeze to make, which is perfect for beginners, but they also impress everyone with their whimsical appearance and tropical flair. Whether you’re gathering for brunch or simply need a sweet escape from the everyday grind, these cookies are bound to steal the show. So, are you ready to delve into this delightful recipe that transforms a traditional favorite into something truly special?

Why Are These Cookies So Special?
Simplicity: With just a few common ingredients, these Pineapple Upside Sugar Cookies come together effortlessly, making them ideal for novice bakers.
Tropical Twist: The juicy pineapple topping adds a refreshing twist, transporting your taste buds to a tropical paradise with every bite.
Endless Variations: Feel free to get creative! Use fresh pineapple or gluten-free flour to customize these cookies to suit your preferences.
Crowd-Pleasing Treat: Perfect for parties or brunch, their vibrant look and flavor are sure to impress guests, just like my Creme Brulee Cookies and French Toast Cookies.
Make-Ahead Magic: You can bake a batch and freeze them, ensuring you have a sweet treat ready whenever a craving strikes!
Pineapple Upside Sugar Cookies Ingredients
For the Cookie Dough
- Unsalted Butter – Adds richness and moisture; ensure it’s softened for easy creaming.
- Granulated Sugar – Sweetens and tenderizes the cookies, making them melt-in-your-mouth delicious.
- Egg – Binds the ingredients together, adding moisture and structure to the dough.
- Vanilla Extract – Elevates the overall flavor, enhancing the sweetness and warmth of the cookies.
- All-Purpose Flour – Forms the foundation of the cookie dough, providing necessary structure.
- Baking Soda – Acts as a leavening agent, ensuring your cookies rise just right.
- Salt – Balances out the sweetness, bringing all the flavors together harmoniously.
For the Pineapple Topping
- Canned Pineapple Rings – Provides a delightful tropical flavor; make sure to drain and pat dry to avoid excess moisture.
- Additional Sugar for Sprinkling – Adds a crunchy topping that not only enhances sweetness but also gives a beautiful finish.
Unlock the magic of homemade treats with these Pineapple Upside Sugar Cookies that are sure to be a hit at any gathering!
Step‑by‑Step Instructions for Pineapple Upside Sugar Cookies
Step 1: Preheat and Prepare
Preheat your oven to 350°F (175°C) and line two baking sheets with parchment paper for easy cleanup. This will ensure even baking and prevent the cookies from sticking. While the oven heats, gather your ingredients for the Pineapple Upside Sugar Cookies so everything is within reach for a smooth cooking experience.
Step 2: Cream Butter and Sugar
In a large mixing bowl, cream together 1 cup of softened unsalted butter and 1 cup of granulated sugar using an electric mixer. Beat on medium speed for about 2-3 minutes until the mixture is light and fluffy, and you see a pale color change. This step is crucial for achieving a soft and tender texture in your cookies.
Step 3: Mix in Egg and Vanilla
Next, add 1 large egg and 1 teaspoon of vanilla extract to the creamed mixture. Beat well until all ingredients are fully combined and smooth. This will add richness and flavor to your Pineapple Upside Sugar Cookies, making the dough deliciously aromatic as you mix.
Step 4: Combine Dry Ingredients
In a separate bowl, whisk together 2 cups of all-purpose flour, 1 teaspoon of baking soda, and ½ teaspoon of salt. Gradually add this dry mixture to the wet components, mixing slowly until a soft cookie dough forms. This dough should be slightly sticky, but manageable, ensuring each cookie has a great structure.
Step 5: Shape the Cookies
Using a tablespoon, scoop out portions of the cookie dough and roll them into balls. Flatten each ball slightly and space them about 2 inches apart on the prepared baking sheets. This gives the Pineapple Upside Sugar Cookies room to spread and rise while baking, resulting in delightful, airy cookies.
Step 6: Add Pineapple Topping
Drain and pat dry your canned pineapple rings thoroughly, removing excess moisture. Place a ring on top of each dough disk, pressing down gently to secure it in place. Finally, sprinkle a little extra sugar over each pineapple to enhance its caramelization and create a beautiful finish on top of the cookies.
Step 7: Bake the Cookies
Transfer the baking sheets to the preheated oven and bake for 12-14 minutes, or until the edges are golden brown and the cookies are firm to the touch. You want to keep an eye on them; they should look slightly puffed and fragrant when done, filling your kitchen with a delightful aroma.
Step 8: Cool and Serve
Once baked, remove the cookies from the oven and allow them to cool on the baking sheets for 5 minutes. Then, carefully transfer the Pineapple Upside Sugar Cookies to a wire rack to cool completely. This ensures they maintain their shape while cooling and gets you ready to enjoy or serve this tropical treat!

What to Serve with Pineapple Upside Sugar Cookies
The perfect meal accompaniment can elevate your Pineapple Upside Sugar Cookies into a delightful dining experience, offering a vibrant taste of summer.
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Iced Chai: The spiced notes of iced chai beautifully complement the sweet pineapple and buttery cookies, making each sip a refreshing contrast.
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Pineapple Iced Tea: Bright and fruity, this chilled tea enhances the tropical flavors, creating a delightful harmony with the cookies.
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Coconut Cream Pie: A creamy, delightful dessert that pairs wonderfully with the cookies, offering a rich texture and a burst of coconut flavor.
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Fresh Fruit Salad: A colorful mix of summer fruits brings a refreshing crunch, balancing the sweetness of the cookies and making for a light dessert option.
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Whipped Cream: A dollop of light, airy whipped cream adds a rich, creamy layer that pairs with the chewy cookie texture for a dessert that feels fancy.
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Vanilla Ice Cream: Serve a warm cookie topped with a scoop of vanilla ice cream, allowing the heat to melt it ever so slightly for an indulgent treat.
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Coconut Water: This light, hydrating beverage adds a touch of tropical flavor, making it a perfect pairing that doesn’t compete with the cookies’ sweetness.
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Tropical Smoothie: Blend up a refreshing smoothie made with mango and banana for a fun and fruity side that complements the flavor profile of the cookies.
Elevate your dessert gathering with these delightful pairings that bring out the best in every bite of your Pineapple Upside Sugar Cookies!
How to Store and Freeze Pineapple Upside Sugar Cookies
Room Temperature: Store cookies in an airtight container for up to 3 days to keep them fresh and soft. This prevents moisture loss while maintaining their delightful texture.
Fridge: For extended freshness, place the cookies in the fridge in an airtight container for up to 1 week. Just remember to allow them to come to room temperature before enjoying!
Freezer: These cookies freeze beautifully! Layer them between parchment paper in a freezer-safe container for up to 2 months. Thaw them at room temperature before serving to regain their soft texture.
Reheating: If you prefer warm cookies, pop them in the microwave for about 10-15 seconds. This will revive their buttery goodness and make the pineapple topping even more delightful.
Pineapple Upside Sugar Cookies Variations
Feel free to make these delightful cookies your own with some fun modifications that will enhance their tropical goodness!
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Fresh Pineapple: Use fresh pineapple rings instead of canned for a brighter, more vibrant flavor. Simply slice and prepare your fresh pineapple for the perfect tropical touch.
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Gluten-Free Alternative: Swap out all-purpose flour for a 1:1 gluten-free baking blend, ensuring everyone can enjoy these delicious treats without compromise.
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Coconut Sugar: Replace granulated sugar with coconut sugar for a deeper, caramel-like flavor that adds another layer of tropical sweetness.
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Tropical Toppings: Top cookies with shredded coconut or maraschino cherries for a delightful and colorful twist, making each cookie feel like a mini island escape.
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Flavored Extracts: Add coconut or almond extract to the dough for an enhanced flavor experience that transports you to a beach paradise with every bite.
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Chocolate Drizzle: When the cookies cool, drizzle melted chocolate on top of the pineapple for a decadent addition that will elevate your cookie game.
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Spice It Up: Add a pinch of cinnamon or nutmeg to the dough for a warm spice that complements the pineapple beautifully, giving a touch of cozy flavor.
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Frozen Treats: Transform these cookies into a fun frozen treat by sandwiching your cookie with a scoop of vanilla ice cream. Serve right away or freeze for a cool, indulgent dessert!
Feel free to mix and match these variations to create the perfect batch of cookies, and don’t hesitate to complement your baking with my Chocolate Chip Cookies for a broader selection of treats. Happy baking!
Expert Tips for Pineapple Upside Sugar Cookies
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Dry the Pineapple: Ensure your canned pineapple rings are thoroughly drained and patted dry to prevent excess moisture from affecting the cookie texture.
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Proper Dough Consistency: If the dough feels too sticky, add a little more flour, but avoid adding too much to maintain the cookie’s soft texture.
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Even Baking: Space the cookie dough balls at least 2 inches apart on the baking sheet to allow for proper spreading and even baking of your Pineapple Upside Sugar Cookies.
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Watch the Time: Keep an eye on the cookies during the last few minutes of baking; they should be golden at the edges but still soft in the center.
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Experiment with Toppings: For a fun twist, try adding a cherry or shredded coconut on top along with the pineapple for added texture and flavor.
Make Ahead Options
These Pineapple Upside Sugar Cookies are a fantastic choice for meal prep enthusiasts! You can prepare the cookie dough up to 24 hours in advance, allowing you to save time on busy baking days. Simply follow the recipe up to shaping the cookies, then wrap the dough tightly in plastic wrap and refrigerate. If you want to freeze the dough, form the cookie balls and place them on a parchment-lined baking sheet in the freezer for about an hour before transferring them to a zip-top bag; they can last up to 3 months. When you’re ready to bake, arrange the frozen dough on a baking sheet, add the pineapple topping, and bake directly from the freezer, adding a couple of extra minutes to the baking time. This way, you’ll enjoy warm, freshly baked Pineapple Upside Sugar Cookies with minimal effort whenever the craving strikes!

Pineapple Upside Sugar Cookies Recipe FAQs
How do I choose ripe pineapple for topping?
Absolutely! When selecting fresh pineapple, look for fruits that are slightly soft to the touch and have a sweet smell at the base. The skin should be a golden-yellow color, indicating ripeness. Avoid pineapples with dark spots or a hard exterior, as they tend to be unripe or overripe. Fresh pineapple gives the cookies a vibrant flavor that can’t be beat!
How should I store leftover cookies?
Very! You can store your Pineapple Upside Sugar Cookies in an airtight container at room temperature for up to 3 days to keep them soft and fresh. If you want them to last longer, place the cookies in the refrigerator for up to a week—just remember to let them come to room temperature before enjoying!
Can I freeze these cookies for later?
Absolutely! To freeze your cookies, layer them between sheets of parchment paper in an airtight freezer-safe container. They can be frozen for up to 2 months. When you’re ready to enjoy them, simply thaw the cookies at room temperature for about 30 minutes. If you prefer them warm, a quick 10-15 seconds in the microwave will revive their glorious texture!
What if the cookie dough is too sticky?
No worries! If you find that your dough feels too sticky, try adding a bit more flour, one tablespoon at a time, until it’s manageable but still soft. Be cautious not to add too much flour, as that can lead to dense cookies. You want the dough to be just slightly tacky for the best texture.
Are these cookies safe for people with allergies?
Great question! This recipe contains gluten (from all-purpose flour) and dairy (in the butter). For a gluten-free version, substitute the all-purpose flour with a gluten-free 1:1 baking blend. If you’re concerned about allergies, always double-check your ingredients, especially the canned pineapple, for any hidden allergens.
Can I make these cookies ahead of time?
Definitely! You can prepare the cookie dough in advance and refrigerate it for up to 3 days. Just wrap it tightly in plastic wrap before chilling. When you’re ready to bake, let the dough warm slightly at room temperature, then follow the usual steps to shape and bake your Pineapple Upside Sugar Cookies for fresh, homemade goodness!

Pineapple Upside Sugar Cookies: A Tropical Twist for Fun Baking
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 1 cup of softened unsalted butter and 1 cup of granulated sugar using an electric mixer.
- Add 1 large egg and 1 teaspoon of vanilla extract to the creamed mixture. Beat well until all ingredients are fully combined.
- In a separate bowl, whisk together 2 cups of all-purpose flour, 1 teaspoon of baking soda, and ½ teaspoon of salt. Gradually add this dry mixture to the wet components.
- Using a tablespoon, scoop out portions of the cookie dough and roll them into balls. Flatten each ball slightly and space them about 2 inches apart on the prepared baking sheets.
- Drain and pat dry your canned pineapple rings thoroughly. Place a ring on top of each dough disk, pressing down gently.
- Transfer the baking sheets to the preheated oven and bake for 12-14 minutes, or until the edges are golden brown and the cookies are firm.
- Once baked, remove the cookies from the oven and allow them to cool on the baking sheets for 5 minutes.

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