Introduction: A Sweet Escape in Every Bite
There’s something instantly nostalgic and heartwarming about pineapple upside-down cake. Its bright, glossy fruit topping, rich caramel notes, and old-school flair take us back to family gatherings, summer picnics, and Sunday dinners. But what if we told you that you could capture all the flavor and fun of this iconic dessert in the form of a soft, buttery cookie?
Pineapple Upside Sugar Cookies combine the chewy, sugary texture of a classic sugar cookie with the tropical flavor and flair of pineapple and maraschino cherries. They’re visually stunning, packed with flavor, and easy enough for a weekday baking session—but special enough for holidays, bake sales, and backyard parties.
This recipe brings together the best of two dessert worlds in one bite-sized, sunny treat that’s perfect for pineapple lovers and cookie enthusiasts alike.
-A Brief History of Pineapple Upside-Down Desserts
The pineapple upside-down cake has been a staple in American baking since the early 1900s, when pineapple became widely available in canned form thanks to companies like Dole. The cake’s fame took off in the 1920s, during the rise of novelty desserts that were easy to make, visually appealing, and perfect for showcasing canned fruits.
With its caramelized brown sugar base, ringed pineapples, and bright red maraschino cherries, it became an iconic dessert, especially in the South. Over the decades, home bakers have reimagined the flavor in muffins, cupcakes, cheesecakes, and now—cookies.
These Pineapple Upside Sugar Cookies offer a modern spin on that classic cake, maintaining the sweet fruit-forward flavor while adding a soft, chewy cookie base for a truly irresistible treat.
-Why You’ll Love Pineapple Upside Sugar Cookies
Bright, fruity flavor in every bite
Soft and chewy sugar cookie base that melts in your mouth
Easy to make with simple ingredients
Fun and festive appearance with pineapple and cherry toppings
Perfect for spring and summer events, Mother’s Day, or even holiday cookie swaps
-Ingredients You’ll Need
Let’s dive into the simple ingredients that come together to make these cookies shine:
For the Sugar Cookie Dough:
1 cup unsalted butter, softened – The base of a rich, tender sugar cookie
1 cup granulated sugar – For sweetness and structure
1 large egg – Binds the dough and adds richness
1 teaspoon vanilla extract – For aroma and depth
2 ½ cups all-purpose flour – Provides the cookie’s structure
½ teaspoon baking powder – For a gentle lift and soft texture
¼ teaspoon salt – Enhances overall flavor
For the Pineapple Topping:
½ cup crushed pineapple, well-drained – Adds tropical sweetness and texture
Maraschino cherries, halved – For that classic “upside-down” look and flavor
> Tip: Drain the pineapple very well to avoid excess moisture in the dough.
-Step-by-Step Instructions
1. Preheat Your Oven
Set the oven to 350°F (175°C). Line a baking sheet with parchment paper or a silicone baking mat to prevent sticking.
2. Cream the Butter and Sugar
In a large mixing bowl, beat the softened butter and granulated sugar together until light and fluffy—about 2 to 3 minutes.
3. Add Wet Ingredients
Mix in the egg and vanilla extract, beating until well combined.
4. Add the Dry Ingredients
In a separate bowl, whisk together the flour, baking powder, and salt. Gradually add the dry ingredients to the wet, mixing just until combined. Do not overmix.
> Optional: Chill the dough for 20 minutes if it feels too soft—this helps with shaping.
5. Shape and Fill
Scoop tablespoon-sized balls of dough and place them on the baking sheet, spacing 2 inches apart. Use your thumb or the back of a spoon to create a small indentation in each cookie.
Fill each indentation with about ½ teaspoon of crushed pineapple, then gently press a halved maraschino cherry into the center.
6. Bake
Bake for 10–12 minutes, or until the edges are set and lightly golden. Don’t overbake—the centers should remain soft.
7. Cool
Allow cookies to cool on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely. The pineapple topping will set as they cool.
-Baking Tips for the Best Cookies
Drain the pineapple well: Press it gently in a sieve or paper towel to remove excess liquid. This prevents soggy cookies.
Use room temperature butter and egg: This helps the dough come together smoothly and bake evenly.
Don’t overmix: Overworking the dough can lead to tough cookies. Stop mixing once the flour is incorporated.
Chill the dough if it feels sticky: It helps the cookies hold their shape during baking.
Bake on the center rack for even browning.
-Flavor Variations to Try
These cookies are highly adaptable. Here are a few fun twists to keep the flavor fresh:
1. Toasted Coconut Topping
Sprinkle sweetened toasted coconut flakes over the pineapple before baking for a tropical crunch.
2. Pineapple Cream Cheese Cookies
Add a dollop of sweetened cream cheese in the center with the pineapple for a richer version.
3. Brown Sugar Cookie Base
Swap half of the granulated sugar with light brown sugar for a deeper, caramel flavor.
4. Lime Zest Infusion
Add 1 teaspoon of lime zest to the dough for a citrusy lift that complements the pineapple.
5. Pineapple-Cherry Jam Glaze
Warm 2 tablespoons of pineapple preserves and drizzle over the cookies after baking.
-Serving Suggestions
These cookies are perfect for a variety of occasions:
Summer BBQs and picnics
Birthday parties or baby showers
Easter or Mother’s Day brunch tables
Afternoon tea or coffee snack
Holiday cookie platters for something different and refreshing
Pair with a light herbal tea, lemonade, or sparkling water with fresh fruit for a delightful combo.
-Storage and Freezing Tips
Storage:
Store cooled cookies in an airtight container at room temperature for up to 3 days. For longer shelf life, refrigerate for up to a week.
Freezing:
To freeze, layer cooled cookies between sheets of parchment paper in a sealed container or freezer bag. Freeze for up to 2 months. Thaw at room temperature before serving.
> Make Ahead: You can prepare the dough and refrigerate it for up to 48 hours before baking.
-Backstory: The Day Pineapple Met Cookie Dough
The first time I made these cookies, I had a fridge full of baking basics—but no fresh fruit. What I did have was a half-used can of crushed pineapple and a jar of maraschino cherries left over from a party.
Not in the mood for a full pineapple upside-down cake, I thought, “Why not sugar cookies?” I scooped the dough, added a tiny spoonful of pineapple and a cherry on top, and baked them like thumbprint cookies.
The results were better than I imagined—buttery and chewy with bursts of tropical sweetness, and a colorful appearance that made them impossible to resist. Since then, they’ve become a go-to for when I want something quick, fruity, and unique.
Now, anytime someone tries them, the first thing they say is, “These taste like a tropical vacation.” And honestly? They do.
-Frequently Asked Questions
Can I use fresh pineapple instead of canned?
Yes, but make sure to dice it very small and drain it thoroughly to avoid excess moisture.
Can I make these gluten-free?
Absolutely. Use a 1:1 gluten-free flour blend, and make sure your baking powder is gluten-free.
Can I leave off the cherries?
Of course! You can replace them with pineapple only, or try dried cranberries or a slice of strawberry for a different look and flavor.
Can I make these into cookie bars instead?
Yes! Press the dough into a greased 9×9-inch pan, top with pineapple and cherries, and bake for 20–25 minutes. Cool completely before slicing.
-Fun Facts About Pineapples, Cookies, and Upside-Down Desserts
Pineapples symbolize hospitality and warmth, which is why they’re popular in home decor and festive recipes.
Sugar cookies date back to the 1700s in Pennsylvania, originally made by German settlers.
The upside-down cake technique became popular in the 1920s thanks to cast iron skillets and canned fruit.
Maraschino cherries were originally preserved in maraschino liqueur—not syrup!
-Conclusion: The Cookies That Bring Sunshine to Every Occasion
Pineapple Upside Sugar Cookies are more than just another cookie recipe—they’re a tropical treat with a nostalgic twist, wrapped in the convenience of a handheld dessert.
With their soft centers, sweet fruit topping, and burst of color, they’re sure to become a fast favorite in your kitchen. Whether you’re baking for a crowd, treating yourself, or bringing a little sunshine to someone’s day, these cookies never disappoint.
-Try Them, Share Them, Bake Them Again
So the next time you find a can of pineapple in the pantry or crave a dessert that’s fun, fruity, and easy, reach for this recipe. You’ll find yourself making them again and again—and everyone who tries them will be asking for the recipe.
