Looking for a dessert that delivers sunshine in every bite? These pineapple upside sugar cookies take everything we love about the iconic pineapple upside-down cake and transform it into a chewy, handheld delight. If you’re craving something fruity, nostalgic, and utterly satisfying, this cookie recipe is your answer. In this article, we’ll walk through the heartwarming origin of the recipe, what makes it so crave-worthy, how to bake it step by step, and tips to perfect it every time.
Table of Contents
Pineapple Upside Sugar Cookies – Where It All Began
The First Bite of Island Sunshine
Back when I was five, I stood on a stool in my grandma’s kitchen, watching her carefully spoon brown sugar and pineapple slices into a cake pan. Her pineapple upside-down cake was legendary in our neighborhood in Asheville. The smell of caramel and butter filled the air, and I’d wait for that glorious flip onto the platter. Years later, as a full-time baker running Sweet Magnolia, I knew I had to reimagine that memory into something fresh—and that’s when pineapple upside sugar cookies were born.
The first version was a happy disaster: too wet, too sticky, but oh-so-delicious. I tweaked the dough, tested different pineapple thicknesses, and finally created a cookie that baked evenly with a golden fruit top. These pineapple upside sugar cookies have become a best-seller at my market booth and one of the most-loved recipes on my blog. They’re buttery and chewy with a top that gets just enough caramelization to echo that iconic cake flavor.
Need a simpler route? This pineapple sugar cookie recipe offers a fruit-infused base perfect for weeknight baking. For beginners, I always recommend this easy pineapple upside-down sugar cookies version, which trims steps without sacrificing flavor.
From Upside‑Down Cake to Hand‑Held Bliss
Why flip a cake when you can hold it in one hand? The idea behind pineapple upside sugar cookies is simple—take the nostalgic goodness of a pineapple upside-down cake and give it a sugar cookie makeover. The buttery dough hugs a pineapple ring and cherry center, baking into a glossy, tropical treat that’s easy to transport and even easier to devour.
Craving more fruity bakes? Don’t miss the classic pineapple sugar cookies for a softer, cake-like cookie base that’s full of island flavor.
What Makes These Pineapple Upside Sugar Cookies Special
Flavor That Pops – Tangy Pineapple Meets Sweet Cookie
If you’ve ever bitten into a pineapple upside-down cake, you know the flavor magic—sweet, juicy pineapple layered over warm brown sugar and butter. These pineapple upside sugar cookies capture that same bold bite, but in a soft, chewy package. The tang from the fruit plays perfectly against a sugar cookie base that’s buttery, slightly crisp on the edges, and rich with vanilla.
What really seals the deal? That maraschino cherry. Nestled in the center of each pineapple ring, it adds color and a pop of sweetness, just like in the classic cake. These cookies offer a full tropical experience in just a few bites. And when baked properly, the brown sugar under the pineapple lightly caramelizes, giving you that crave-worthy glaze on top.
Texture Talk – Chewy Base, Juicy Top
Texture is where these cookies shine. At first glance, you might expect them to be cakey or overly soft, but the balance is what sets them apart. The sugar cookie dough bakes into a sturdy, golden base that’s slightly crisp around the edges and chewy in the center. On top, the pineapple ring retains its juiciness without soaking through, thanks to a light coating of brown sugar and careful baking.
The result? Each bite delivers contrast—the soft, yielding cookie, the lightly candied pineapple, and a burst of cherry. And because they’re baked in muffin tins or on parchment-lined sheets, they hold shape without spreading too thin.
Home bakers love this cookie because it’s forgiving and showstopping. You don’t need piping bags or fancy tools. Just stack the components, bake, and serve. If you’re new to the idea, the pineapple upside sugar cookies recipe lays out the steps clearly and makes it easy to get consistent results every time.
Ingredients & Easy Step‑by‑Step Guide
Ingredients
The best part about these pineapple upside sugar cookies? You likely have most ingredients on hand already. Here’s what you’ll need for the dough and topping:
For the Cookie Dough:
- 1 cup unsalted butter, softened
- 1 cup granulated sugar
- 1 large egg
- 2 teaspoons vanilla extract
- 2½ cups all-purpose flour
- ½ teaspoon baking powder
- ¼ teaspoon salt
For the Topping:
- ½ cup light brown sugar, packed
- 10–12 canned pineapple slices, well-drained and patted dry
- 10–12 maraschino cherries, drained
Optional:
- 1–2 tablespoons pineapple juice (reserved from the can) to add moisture to dough if needed
- Additional brown sugar for garnish
If you want to mix it up, fresh pineapple can work—just cut it into uniform rings and dry thoroughly. A few readers also enjoy using crushed pineapple, though it’s best drained through a fine mesh sieve to avoid sogginess.
Simple Steps to Tropical Cookies
Making pineapple upside sugar cookies is easier than you’d think. Here’s a simple step-by-step:
1. Preheat oven to 350°F (175°C). Lightly grease or line muffin tin with parchment.
2. Cream butter and granulated sugar until light and fluffy.
3. Add egg and vanilla. Mix until combined.
4. Whisk flour, baking powder, and salt in a separate bowl. Add to wet mixture and mix until dough forms.
5. Place 1 tsp brown sugar in bottom of each muffin cup. Add a pineapple ring and a cherry in the center.
6. Scoop dough (about 2 tbsp) and flatten gently over each fruit stack.
7. Bake for 12–15 minutes until edges are golden.
8. Let cool 5 minutes before flipping onto a wire rack.
Pro Tips, Variations & Troubleshooting
Pro Baker Tips for Best Results
Baking pineapple upside sugar cookies is simple, but a few thoughtful techniques will take your cookies from good to bakery-worthy.
Drain your fruit well. The biggest issue bakers face is soggy bottoms. Make sure both the pineapple slices and cherries are fully drained and blotted with paper towels. Extra moisture can cause the cookies to steam instead of bake, ruining the texture.
Use muffin tins for perfect shape. This helps the cookies keep their structure and prevents the topping from spreading too far. Lightly grease or line the tin with parchment rounds to help with release.
Don’t overbake. The bottom sugar layer should caramelize—not burn. Keep a close eye during the last few minutes. When the edges are golden and the center is just set, they’re ready.
Cool before flipping. Let the cookies sit for 5 minutes before removing them from the tin. This helps the caramel set slightly so the topping stays intact. Use a small offset spatula to gently lift them out.
Fun Variations to Try
Want to mix things up? There are plenty of ways to tweak these pineapple upside sugar cookies to fit your style:
Mini pineapple cookies: Cut the pineapple rings in half or use crushed pineapple and bake in mini muffin tins for bite-size versions. Just remember to drain thoroughly.
Add coconut: A sprinkle of shredded coconut in the brown sugar layer adds extra island flavor and texture.
Make it gluten-free: Use a 1:1 gluten-free flour blend. The dough may be slightly more delicate, but it holds up well when chilled before baking.
Switch the fruit: Try peach slices, mango, or even apple rings for a seasonal variation. The sugar cookie base is neutral enough to support a variety of toppings.
Skip the cherry: Not a fan? You can leave it out or swap it with a raspberry for a tarter note.
How to Serve & Store Pineapple Upside Sugar Cookies
Serving Ideas That Wow
These pineapple upside sugar cookies are showstoppers right out of the pan—but a little extra presentation goes a long way. For a tropical dessert platter, arrange the cookies on a vintage cake stand, and sprinkle toasted coconut flakes or lime zest for a fresh finish.
Serving for a summer party? Add a dollop of whipped cream or vanilla bean ice cream beside each cookie. Their fruity caramel top pairs beautifully with creamy sides, making each bite feel like a mini sundae.
You can also wrap individual cookies in wax paper and tie with twine for charming gifts or bake sale treats.
Storage Tips to Keep Them Fresh
These cookies are best the day they’re made, but they store surprisingly well.
- Room Temperature: Place cooled cookies in a single layer in an airtight container. If stacking, add parchment between layers. They’ll stay fresh for up to 2 days.
- Refrigerator: Store up to 5 days—but note, the pineapple may soften the cookie slightly.
- Freezer: Flash-freeze cookies individually, then transfer to a zip-top bag. Reheat in a 300°F oven for 5 minutes to refresh texture.
Want to prep ahead? The cookie dough can be frozen (pre-shaped) and baked straight from the freezer. Just add 2–3 minutes to the baking time.
Whether you’re gifting them, storing them, or prepping them for a crowd, pineapple upside sugar cookies remain a crowd-pleasing treat that never overstays their welcome.
Conclusion
Baking is a memory in motion, and pineapple upside sugar cookies are my way of sharing one of my favorite moments—standing in my grandma’s kitchen, waiting for that cake flip. These cookies capture that joy, in a more accessible, everyday form. They’re soft, vibrant, and full of that caramel-fruit magic.
So whether you’re baking for a party, filling a cookie tin, or just want to brighten your week with a bite of tropical sunshine, give this recipe a try.
Want more sweet inspiration? Follow me on Facebook and Pinterest where I share cozy, easy-to-make baking recipes just like this one. Every bite is a warm hug. Let’s bake something beautiful together.
Print
Pineapple Upside Sugar Cookies
- Total Time: 30 mins
- Yield: 10–12 cookies 1x
- Diet: Vegetarian
Description
Soft and chewy pineapple upside sugar cookies with caramelized pineapple rings and maraschino cherries—a tropical twist on a classic dessert.
Ingredients
1 cup unsalted butter, softened
1 cup granulated sugar
1 large egg
2 teaspoons vanilla extract
2½ cups all-purpose flour
½ teaspoon baking powder
¼ teaspoon salt
½ cup light brown sugar, packed
10–12 canned pineapple slices, well-drained and patted dry
10–12 maraschino cherries, drained
Instructions
1. Preheat oven to 350°F (175°C). Lightly grease or line muffin tin with parchment.
2. Cream butter and granulated sugar until light and fluffy.
3. Add egg and vanilla. Mix until combined.
4. Whisk flour, baking powder, and salt in a separate bowl. Add to wet mixture and mix until dough forms.
5. Place 1 tsp brown sugar in bottom of each muffin cup. Add a pineapple ring and a cherry in the center.
6. Scoop dough (about 2 tbsp) and flatten gently over each fruit stack.
7. Bake for 12–15 minutes until edges are golden.
8. Let cool 5 minutes before flipping onto a wire rack.
Notes
Make sure pineapple is completely dry to prevent soggy cookies.
You can prepare dough ahead and refrigerate for 2 days.
Cookies store best in a single layer in an airtight container.
- Prep Time: 15 mins
- Cook Time: 15 mins
- Category: Dessert
- Method: Baking
- Cuisine: American
Nutrition
- Serving Size: 1 cookie
- Calories: 210
- Sugar: 18g
- Sodium: 70mg
- Fat: 10g
- Saturated Fat: 6g
- Unsaturated Fat: 3g
- Trans Fat: 0g
- Carbohydrates: 28g
- Fiber: 1g
- Protein: 2g
- Cholesterol: 30mg
FAQs About Pineapple Upside Sugar Cookies
Can I use fresh pineapple instead of canned?
Absolutely. Just be sure to cut it into uniform slices and pat them completely dry. Fresh pineapple adds a brighter flavor but may need an extra minute or two in the oven to caramelize fully.
How should I store these cookies to keep them fresh?
Once cooled, store your pineapple upside sugar cookies in an airtight container at room temperature for up to 2 days. If you refrigerate them, use parchment between layers to prevent sticking. You can also freeze them individually.
Can I make the dough ahead of time?
Yes! The sugar cookie dough can be made up to 2 days in advance and stored in the fridge. You can also freeze it pre-shaped. Just bake straight from frozen, adding 2–3 minutes to the time.
Why add a maraschino cherry in the center?
It’s a classic visual and flavor element from the traditional upside-down cake. It adds a pop of color, sweetness, and nostalgia—but you can omit it or replace it with a raspberry or candied ginger if preferred.