If you have a soft spot for classic sugar cookies with a tropical twist, you are going to absolutely adore this Pineapple Upside Sugar Cookies Recipe. It’s a delightful blend of buttery, chewy sugar cookie dough paired perfectly with juicy pineapple slices and bright maraschino cherries, all baked to golden perfection in individual mini cake pans. The combination of the caramelized brown sugar and melted butter gives these cookies an irresistibly rich base, while the fruity topping adds an unexpected pop of freshness. This recipe turns simple ingredients into a charming treat that’s as fun to make as it is to eat—perfect for sharing with friends or savoring as a sunny pick-me-up any time of year.
Ingredients You’ll Need
Every ingredient in this Pineapple Upside Sugar Cookies Recipe plays a simple but crucial role. From the creamy butter that makes the dough soft, to the tangy sour cream that keeps it tender, these basics come together to create a perfectly balanced cookie with rich flavor and fantastic texture.
- Butter (1 cup, room temperature): Provides richness and a tender crumb to the cookie dough.
- Granulated sugar (1 ½ cups): Adds sweetness and helps with browning for golden edges.
- Eggs (2): Bind ingredients together and contribute to the dough’s structure.
- Vanilla extract (2 teaspoons): Enhances flavor with a warm, inviting aroma.
- Sour cream (½ cup): Keeps the cookies moist and soft while adding subtle tanginess.
- All-purpose flour (3 cups): The base of the dough, giving it body and texture.
- Baking powder (1 teaspoon): Leavens the dough just enough for a slight lift.
- Cornstarch (1 teaspoon): Adds softness for a delicate bite.
- Salt (½ teaspoon): Balances sweetness and enhances all the flavors.
- Canned pineapple slices (13): The star of the show, offering juicy bursts of tropical sweetness.
- Maraschino cherries (13): Adds bright color and a cheerful pop of flavor atop each cookie.
- Melted butter (½ cup): Mixed with brown sugar to create a luscious caramel layer beneath the fruit.
- Light brown sugar (1 cup, packed): Combines with melted butter for that classic caramelized taste under the pineapple.
How to Make Pineapple Upside Sugar Cookies Recipe
Step 1: Prepare Your Mini Cake Pans
Preheat your oven to 350°F (175°C) and lightly grease a mini round cake pan. This ensures your Pineapple Upside Sugar Cookies will release easily and maintain their pretty shape after baking. Using mini pans helps you get that charming individual cookie effect with caramelized fruit topping on each one.
Step 2: Cream Butter and Sugar
In a large bowl, beat together the room temperature butter and granulated sugar until the mixture becomes light, fluffy, and pale. This aeration step is key for giving your cookies a tender, melt-in-your-mouth texture that feels so satisfying to bite into.
Step 3: Add Eggs, Vanilla, and Sour Cream
Mix in the eggs one at a time to fully combine, then stir in the vanilla extract and sour cream. The sour cream not only adds moisture but also helps keep the cookies soft even after cooling, which makes this Pineapple Upside Sugar Cookies Recipe stand out from your usual sugar cookie.
Step 4: Incorporate Dry Ingredients
Gradually add the all-purpose flour, baking powder, cornstarch, and salt to the wet mixture, stirring until a soft dough forms. The cornstarch here is a secret weapon—it introduces a tender crumb that balances the cookie’s chewy and cakey qualities perfectly.
Step 5: Prepare the Brown Sugar Caramel Layer
In a separate bowl, stir together the melted butter and packed light brown sugar until smooth. This luscious blend will transform into a caramelized base underneath the pineapple slices, adding a deep, buttery sweetness that pairs wonderfully with the fruity topping.
Step 6: Assemble in Mini Pans
Spoon about 1 tablespoon of the brown sugar mixture into each mini cake cavity. Place one pineapple slice on top, then add a maraschino cherry in the center of the pineapple. This classic combo is what gives these cookies their signature look and flavor punch.
Step 7: Add the Cookie Dough
Top each pineapple slice with roughly 3 tablespoons of cookie dough, pressing gently so it covers the fruit completely. This layering method ensures each bite gives you a harmony of soft cookie, sweet caramel, juicy pineapple, and a burst of cherry.
Step 8: Bake and Cool
Bake your Pineapple Upside Sugar Cookies for 25 minutes or until the edges turn a gorgeous golden brown. Let the cookies cool in the pan for about 10 minutes before carefully turning them out onto wax paper to cool completely. This resting step helps the caramel set and keeps everything from falling apart.
How to Serve Pineapple Upside Sugar Cookies Recipe
Garnishes
For a little extra flair, dust your cookies lightly with powdered sugar or add a small dollop of whipped cream on top. A sprinkle of toasted coconut flakes can also add a wonderful texture contrast and boost the tropical vibe of this Pineapple Upside Sugar Cookies Recipe.
Side Dishes
These cookies pair wonderfully with a creamy vanilla ice cream or a scoop of coconut sorbet for an indulgent dessert experience. You can also serve them alongside fresh fruit salad for a refreshing summer treat that balances sweet and tangy flavors.
Creative Ways to Present
Try serving these cookies on a colorful platter surrounded by fresh pineapple wedges and cherries for a party-worthy presentation. Or arrange them on cupcake wrappers and tie with little ribbons for gifting or special occasions—the charming look is sure to impress anyone lucky enough to try them.
Make Ahead and Storage
Storing Leftovers
Store leftover Pineapple Upside Sugar Cookies in an airtight container at room temperature for up to 3 days. Keeping them sealed will maintain their softness and prevent the pineapple from drying out.
Freezing
You can freeze these cookies after baking by wrapping each one individually in plastic wrap and then placing them in a freezer-safe container. They’ll keep for up to 2 months this way, perfect for making ahead for a party or spontaneous treat cravings.
Reheating
To enjoy your Pineapple Upside Sugar Cookies warm, thaw frozen cookies at room temperature and then pop them in a 300°F (150°C) oven for 5–7 minutes. This brings back that fresh-out-of-the-oven softness and delicious warmth that makes them so comforting.
FAQs
Can I use fresh pineapple instead of canned for the Pineapple Upside Sugar Cookies Recipe?
Fresh pineapple can be used, but canned slices work best because they are uniform and hold their shape well during baking. If using fresh, opt for ripe but firm slices and pat them dry to prevent excess moisture affecting the cookie dough.
What if I don’t have mini round cake pans? Can I use muffin tins?
Absolutely! Muffin tins are a great alternative and will give you a similar individual cookie shape. Just be sure to grease them well and adjust the amount of dough accordingly to avoid overflow.
How do I prevent the cookie dough from leaking around the pineapple?
Press the cookie dough gently but firmly over the pineapple slices to seal the edges. Ensuring your dough is at the right consistency—not too sticky and not too dry—helps it hold up during baking without leaks.
Can I make this Pineapple Upside Sugar Cookies Recipe vegan?
With some modifications, yes! Substitute the butter with a plant-based margarine, replace eggs with flax eggs or another vegan egg substitute, and use a vegan sour cream alternative. Keep in mind texture might vary slightly, but the flavors will still shine.
What is the best way to keep the cherries from fading during baking?
Choose high-quality maraschino cherries that retain their color well, and place them gently on top of the pineapple slices right before baking. Some people also brush a little melted butter on the cherries to keep them moist and vibrant.
Final Thoughts
This Pineapple Upside Sugar Cookies Recipe is a wonderful way to bring a burst of sunshine into your baking routine. With its irresistible combo of buttery cookie dough, caramelized brown sugar, juicy pineapple, and bright cherries, it’s a treat that feels both nostalgic and fresh. I can’t wait for you to try making these at home—they’re sure to become a new favorite that you’ll want to share again and again!
Print
Pineapple Upside Sugar Cookies Recipe
- Total Time: 40 minutes
- Yield: 13 servings 1x
Description
These Pineapple Upside Sugar Cookies combine the tropical sweetness of pineapple and maraschino cherries with a buttery, soft sugar cookie base. Baked in a mini round cake pan, each cookie features a caramelized brown sugar and butter topping that mimics the classic pineapple upside-down cake flavor in a delightful cookie form. Perfect for gatherings or a sweet treat, these cookies are easy to make and irresistibly delicious.
Ingredients
Cookie Dough
- 1 cup butter (room temperature)
- 1 ½ cups granulated sugar
- 2 eggs
- 2 teaspoons vanilla extract
- ½ cup sour cream
- 3 cups all-purpose flour
- 1 teaspoon baking powder
- 1 teaspoon cornstarch
- ½ teaspoon salt
Topping
- 13 canned pineapple slices
- 13 maraschino cherries
- ½ cup melted butter
- 1 cup packed light brown sugar
Instructions
- Preheat and Prepare Pan: Preheat your oven to 350°F (175°C) and lightly grease a mini round cake pan to prevent sticking.
- Cream Butter and Sugar: In a large bowl, use a mixer to cream together the room temperature butter and granulated sugar until the mixture is fluffy and light, which helps create a tender cookie texture.
- Add Wet Ingredients: Beat in the eggs, vanilla extract, and sour cream until the mixture is well combined and smooth.
- Combine Dry Ingredients: Gradually add the all-purpose flour, baking powder, cornstarch, and salt into the wet ingredients, mixing until a soft dough forms.
- Prepare Brown Sugar Mixture: In a separate bowl, stir together the melted butter and packed light brown sugar until the sugar is moistened evenly.
- Assemble Cookies: Spread about 1 tablespoon of the brown sugar mixture evenly into each mini cake pan cavity. Place a pineapple slice on top of the brown sugar in each cavity, then center a maraschino cherry on each pineapple slice.
- Add Cookie Dough: Drop approximately 3 tablespoons of cookie dough on top of each pineapple slice and gently press the dough to cover the fruit completely.
- Bake Cookies: Bake in the preheated oven for 25 minutes, or until the cookies turn golden brown on top.
- Cool and Serve: Let the cookies cool in the pan for 10 minutes to set, then carefully invert them onto wax paper or a cooling rack to cool completely before serving.
Notes
- Use room-temperature butter for easier creaming and better texture.
- Press the dough gently over the pineapple to keep the fruit intact during baking.
- Use mini round cake pans or an equivalent muffin tin if mini pans are unavailable.
- Ensure cookies are fully cooled before removing from the pan to maintain shape.
- For a dairy-free version, substitute sour cream with a dairy-free yogurt alternative.
- Prep Time: 15 minutes
- Cook Time: 25 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
