As I gazed at the vibrant pineapple rings glistening in the baking tray, memories of summer barbecues and family gatherings flooded my mind. Transforming the classic pineapple upside-down cake into these delightful Pineapple Upside Down Sugar Cookies is not just a recipe; it’s a journey back to those joyful moments. This easy-to-follow recipe brings together a buttery softness that melts in your mouth, making it a total crowd-pleaser. Perfect for potlucks, these tropical treats not only whisper of sunshine and laughter, but they’re also surprisingly quick to whip up, leaving you with more time to enjoy your favorite company. What’s your favorite cookie to bake when the mood strikes?

Why Choose Pineapple Upside Down Cookies?
Easy Transformation: You’ll love how this recipe turns a beloved cake into cookies without complicated steps.
Tropical Flavor: The burst of pineapple adds a refreshing twist that makes every bite feel like summer.
Crowd-Pleaser: Perfect for potlucks or gatherings, these cookies will impress friends and family alike.
Quick Prep Time: In just a few simple steps, you can whip up these delightful treats and have them ready to share.
Customizable Delight: Feel free to experiment with different fruits or extracts to make this recipe your own! If you enjoy unique cookie creations, don’t forget to check out Meringue Cookies Homemade and Chocolate Oat Cookies.
Pineapple Upside Down Sugar Cookies Ingredients
For the Dough
- Unsalted Butter – Provides richness and moisture; ensure butter is softened, not melted for better dough consistency.
- Granulated Sugar – Sweetness and helps create a crisp edge; can substitute with coconut sugar for a different flavor profile.
- Large Egg – Binds ingredients and adds moisture, contributing to the cookie’s structure.
- Vanilla Extract (optional) – Adds depth of flavor; can substitute with almond extract for a different taste.
- All-Purpose Flour or Gluten-Free Blend – Main structure; for gluten-free, ensure a high-quality 1:1 blend.
- Baking Soda – Leavening agent that helps the cookies rise.
- Salt – Balances sweetness and enhances flavor; a small amount goes a long way.
For the Topping
- Canned Pineapple Rings – Topping that provides moistness and a tropical twist; ensure they are well-drained, or you can use fresh pineapple as a delicious alternative.
- Additional Sugar for Sprinkling – Helps caramelize the pineapple during baking, enhancing the flavor of these Pineapple Upside Down Sugar Cookies.
Step‑by‑Step Instructions for Pineapple Upside Down Sugar Cookies That Delight Every Bite
Step 1: Preheat and Prepare
Begin by preheating your oven to 350°F (180°C). While the oven is heating, line your baking trays with parchment paper to ensure the cookies bake evenly and don’t stick. This preparation step is essential for achieving those delightful Pineapple Upside Down Sugar Cookies that boast a golden color and soft texture.
Step 2: Cream Butter and Sugar
In a large mixing bowl, use an electric mixer to cream together 1 cup of softened unsalted butter and 1 cup of granulated sugar for about 2-3 minutes, until the mixture is light and fluffy. This step helps incorporate air, resulting in tender cookies. Make sure to scrape down the sides of the bowl to ensure even mixing as you go.
Step 3: Add Eggs and Flavor
Next, crack in 1 large egg and add a splash of vanilla extract to the buttery mixture. Beat the ingredients together until fully combined, which should take about a minute. The dough will become creamy and aromatic, ready to bring the sweet taste of summer to your Pineapple Upside Down Sugar Cookies.
Step 4: Mix Dry Ingredients
In a separate bowl, whisk together 2 cups of all-purpose flour, 1 teaspoon of baking soda, and a pinch of salt until well combined. This step ensures the leavening agent and salt are evenly distributed throughout the dry ingredients. Gradually add the dry mixture to the wet ingredients, mixing gently until a soft dough forms without overworking it.
Step 5: Scoop the Dough
Using a cookie scoop or a spoon, scoop out about 2 tablespoons of dough and drop them onto the prepared baking trays, leaving enough space between each mound for spreading—about 2 inches apart. This spacing is crucial to ensure your Pineapple Upside Down Sugar Cookies bake evenly and achieve that perfect shape.
Step 6: Add Pineapple and Sugar
Take a well-drained canned pineapple ring and press one gently into the center of each dough ball. To enhance the caramelization of the pineapple during baking, sprinkle a little extra granulated sugar over the top of each cookie. This will add a delightful sweetness and a satisfying, crispy texture to your cookies.
Step 7: Bake to Perfection
Place the trays in your preheated oven and bake for 11-13 minutes. Keep an eye on them as they bake; the cookies are ready when the edges turn a lovely golden brown and the centers are set. The aroma of warm pineapple and sweetness will surely fill your kitchen, making your mouth water in anticipation.
Step 8: Cooling Time
Once baked, remove the trays from the oven and allow the cookies to cool on the tray for about 5 minutes. This cooling time helps them firm up a bit and makes them easy to transfer. After they’ve cooled slightly, move the delightful Pineapple Upside Down Sugar Cookies to a wire rack to cool completely, ensuring they maintain their wonderful texture.

What to Serve with Pineapple Upside Down Sugar Cookies
Transport your taste buds to a sunny paradise with a delightful meal that perfectly complements these tropical treats.
- Whipped Cream: A light, airy topping that adds a creamy touch and balances the cookie’s sweetness wonderfully.
- Vanilla Ice Cream: The classic pairing that enhances the cookies’ tropical flavor with cool, creamy richness.
- Coconut Rice: This subtly sweet and fluffy side dish mirrors the tropical vibe, creating a harmonizing theme throughout your meal.
- Fresh Fruit Salad: A colorful medley of fresh fruits elevates the tropical essence, adding bright flavors and textures that excite the palate.
- Iced Tea: A refreshing drink choice, it provides a subtle sweetness and a hint of citrus that pairs beautifully with the cookies.
- Lemonade: The tartness of lemonade cuts through the sweetness, providing a refreshing contrast that will leave everyone wanting more.
- Cream Cheese Frosting: A swirl of this tangy frosting can elevate the cookies into a luscious dessert experience.
- Chocolate Dipping Sauce: For those who adore chocolate, a simple drizzle can introduce a rich, sweet contrast to the fruity cookies.
- Tropical Smoothie: Blend up some frozen pineapple with coconut milk for a creamy drink that mirrors the cookie’s tropical vibes and makes your meal feel festive.
Storage Tips for Pineapple Upside Down Sugar Cookies
Room Temperature: Store cookies in an airtight container for up to 3 days at room temperature to maintain their delightful texture.
Freezer: For longer storage, freeze cookies in a single layer on a baking tray. Once firm, transfer to a freezer-safe container for up to 2 months.
Thawing: Thaw cookies at room temperature for about 30 minutes before serving, ensuring they taste just as fresh as the day they were baked.
Reheating: To restore warmth and softness, gently reheat cookies in a preheated oven at 300°F (150°C) for about 5 minutes. Enjoy your Pineapple Upside Down Sugar Cookies!
Pineapple Upside Down Sugar Cookies Variations
Get ready to unleash your creativity in the kitchen with these delightful twists on the classic recipe!
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Gluten-Free: Substitute all-purpose flour with a high-quality 1:1 gluten-free baking blend for a similar taste and texture. Your gluten-free friends will thank you!
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Tropical Twist: Use canned peaches or cherries instead of pineapple for a vibrant and fruity change. This simple swap can transport you to an island paradise with each bite.
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Coconut Delight: Add unsweetened shredded coconut to the cookie dough for an extra layer of tropical flavor. The chewy texture enhances the nostalgic feel of summer.
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Almond Extract: Switch out vanilla extract for almond extract for a nutty flavor profile. This subtle change can elevate your cookies into an unforgettable treat.
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Spicy Kick: Introduce a sprinkle of cinnamon or nutmeg in the dough for a warm, cozy twist. These spices work wonderfully and add a comforting aroma as they bake.
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Chocolate Drizzle: Drizzle melted chocolate over the cooled cookies for a decadent finish. Pairing pineapple with chocolate creates an unexpectedly delightful combination.
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Mini Cookie Bites: Make smaller, bite-sized cookies for a fun party treat. They’re perfect for snacking and allow guests to enjoy multiple flavors without overindulging.
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Garnish with Mint: Top each cookie with a fresh mint leaf before serving for a gorgeous presentation. The mint adds a refreshing touch that complements the sweet pineapple beautifully.
Experimenting with these variations can add exciting dimensions to your Pineapple Upside Down Sugar Cookies! And if you’re in the mood for more cookie inspiration, check out my delightful Pecan Snowball Cookies and follow that up with a luxurious Sugar Cookie Cheesecake. Enjoy your cookie-making adventure!
Expert Tips for Pineapple Upside Down Sugar Cookies
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Butter Matters: Use softened butter to achieve the right texture. Melted butter can lead to overly spread cookies, making them flat.
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Chill If Needed: If your cookie dough spreads too much while baking, refrigerate it for 20 minutes before scooping it onto the tray.
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Sugar Sprinkle: Don’t skip the extra sugar topping! It caramelizes the pineapple and adds a delightful crunch to your Pineapple Upside Down Sugar Cookies.
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Perfect Pineapple Placement: Ensure pineapple rings are well-drained to prevent excess moisture that can affect the cookie’s texture.
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Flavor Experimentation: Feel free to swap out fruit toppings! Cherries or peaches also make for delicious, customizable variations to your cookies.
Make Ahead Options
These Pineapple Upside Down Sugar Cookies are a fantastic choice for meal prep enthusiasts looking to save time on busy days! You can prepare the cookie dough up to 24 hours in advance, simply scoop it onto the baking trays and refrigerate them covered. The pineapple can also be placed on top of each dough ball just before baking. When you’re ready to serve, preheat your oven and bake the cookies directly from the fridge for 11-13 minutes until they’re golden and fragrant. This method ensures the cookies remain just as delicious and fresh, making it easy to enjoy a sweet treat whenever the craving strikes!

Pineapple Upside Down Sugar Cookies Recipe FAQs
What type of pineapple is best for these cookies?
Absolutely go for well-drained canned pineapple rings for this recipe. They maintain moisture while baking, and their sweetness perfectly complements the buttery cookie. If you prefer fresh pineapple, make sure to slice it thin and pat it dry to avoid excess moisture in the cookies.
How should I store leftover cookies?
For optimal texture, store your Pineapple Upside Down Sugar Cookies in an airtight container at room temperature for up to 3 days. If you want to keep them longer, you can freeze the cookies. Simply lay them out in a single layer on a baking sheet until frozen, then transfer them to a freezer-safe container for up to 2 months.
Can I freeze these cookies?
Yes! Freezing is a great option to keep your Pineapple Upside Down Sugar Cookies fresh. Place them in a single layer on a baking sheet first, freeze until firm, and then store them in a freezer-safe bag or container. When you’re ready to enjoy, let them thaw at room temperature for about 30 minutes before serving.
What should I do if my cookies spread too much while baking?
If you notice that your cookies spread too much, don’t worry! This can often happen if the butter is too warm. To fix this, simply chill the dough for about 20 minutes before scooping it onto the baking tray. This will help firm up the dough, leading to more controlled spreading during baking.
Any dietary tips for these cookies?
Absolutely! If you’re looking for gluten-free options, swap the all-purpose flour for a high-quality 1:1 gluten-free flour blend. Additionally, you can replace the sugar with coconut sugar to provide a slightly different flavor profile while making the recipe even more enjoyable for a variety of diets.
How can I enhance the flavor of my cookies?
To elevate the flavor of your Pineapple Upside Down Sugar Cookies, consider adding a splash of almond or coconut extract for a delightful twist. You can also top the cookies with a mix of tropical fruits like cherries or peaches for an exciting flavor combination that’ll keep everyone guessing and loving every bite!

Pineapple Upside Down Sugar Cookies That Delight Every Bite
Ingredients
Equipment
Method
- Preheat your oven to 350°F (180°C) and line your baking trays with parchment paper.
- Cream together 1 cup of softened unsalted butter and 1 cup of granulated sugar for 2-3 minutes until light and fluffy.
- Add in 1 large egg and 1 teaspoon of vanilla extract, mixing until fully combined.
- In a separate bowl, whisk together 2 cups of all-purpose flour, 1 teaspoon of baking soda, and a pinch of salt. Gradually mix into the wet ingredients.
- Scoop about 2 tablespoons of dough onto the baking trays, spacing them about 2 inches apart.
- Press a well-drained canned pineapple ring into the center of each dough ball and sprinkle with additional sugar.
- Bake for 11-13 minutes until edges are golden brown and centers are set.
- Cool on the tray for 5 minutes before transferring to a wire rack to cool completely.

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