If you’re craving a cookie that bursts with tropical charm and a delightful twist, you’re in for a treat with the Pineapple Upside Sugar Cookies Recipe. These little gems combine the buttery sweetness of classic sugar cookies with a luscious pineapple slice and cherry nestled on top, all baked upside down to create a caramelized, colorful crown. It’s like a mini dessert party in every bite, perfectly balanced between chewy, tender dough and the juicy fruit topping. Whether for a sunny afternoon snack or a showstopping addition to your next gathering, this recipe offers a playful spin that’s as fun to make as it is to eat.
Ingredients You’ll Need
Gathering simple, easy-to-find ingredients is the key to making these scrumptious cookies shine. Each component plays its own role in delivering a beautiful balance of texture, flavor, and that irresistible tropical vibe.
- 1 cup butter (room temperature): Creates a tender, rich base for the cookie dough and adds luscious flavor.
- 1 ½ cups granulated sugar: Sweetens and helps achieve the perfect fluffy texture.
- 2 eggs: Bind everything together and provide moisture to keep cookies soft.
- 2 teaspoons vanilla extract: Brings warmth and depth to the overall flavor.
- ½ cup sour cream: Adds tenderness and a subtle tang that keeps the dough soft and moist.
- 3 cups all-purpose flour: The sturdy structure for a cookie that holds its shape while remaining chewy.
- 1 teaspoon baking powder: Helps the cookies rise just enough without puffing up too much.
- 1 teaspoon cornstarch: Ensures a delicate crumb and light texture.
- ½ teaspoon salt: Balances the sweetness and enhances all the flavors.
- 13 canned pineapple slices: The star topping, offering juicy, tropical brightness.
- 13 maraschino cherries: Pops of color and sweet tartness that perfectly complement the pineapple.
- ½ cup melted butter: Mixed with brown sugar to create the sticky, caramel-like base for topping.
- 1 cup packed light brown sugar: Adds deep molasses notes and caramelizes beautifully under the fruit.
How to Make Pineapple Upside Sugar Cookies Recipe
Step 1: Prep Your Oven and Pan
Start by preheating your oven to 350°F (175°C). Lightly grease a mini round cake pan—this small detail helps those charming pineapple-topped cookies release effortlessly after baking. A mini pan is perfect for individual servings, turning each cookie into its own little tropical treat.
Step 2: Cream Butter and Sugar
In a large bowl, cream together the softened butter and granulated sugar until fluffy and light in color. This step is crucial because it incorporates air, setting the stage for tender, melt-in-your-mouth cookies that have just the right amount of softness and chew.
Step 3: Add Eggs, Vanilla, and Sour Cream
Beat in the eggs one at a time, then mix in the vanilla extract and sour cream until everything is beautifully combined. The sour cream is the secret ingredient that keeps these cookies delightfully moist, while the vanilla adds a rich, aromatic lift.
Step 4: Combine Dry Ingredients Gradually
In a separate bowl, whisk the all-purpose flour, baking powder, cornstarch, and salt. Slowly add this dry mixture to the wet ingredients, stirring just until a soft dough forms. Be careful not to overmix, or the cookies could turn tough instead of tender.
Step 5: Prepare the Brown Sugar Topping
In a small bowl, mix together the melted butter and light brown sugar. This luscious blend is what gives the cookies that irresistible caramelized base once baked. The combination will fluff up slightly and bubble up around the pineapple in the oven.
Step 6: Assemble the Cookies in the Pan
Spoon about one tablespoon of the brown sugar mixture into each cavity of your mini pan, spreading it evenly. Next, top each with a pineapple slice and nestle a maraschino cherry right in the center of the pineapple—that signature look that makes this recipe a showstopper.
Step 7: Add the Cookie Dough
Drop three tablespoons of the cookie dough on top of each pineapple slice, gently pressing it down just enough to cover the fruit but keep it from flattening completely. This layering will bake up into a golden, tender cookie that hugs the sweet toppings perfectly.
Step 8: Bake and Cool
Bake for 25 minutes or until the cookies turn golden brown on top. The ovens’ warmth caramelizes the brown sugar and juices from the pineapple, creating an irresistibly sticky, flavorful base. Once baked, cool the cookies in the pan for 10 minutes to set, then carefully turn each upside down onto waxed paper to cool completely. This flip reveals the stunning pineapple and cherry crown, making your cookies as beautiful as they are delicious.
How to Serve Pineapple Upside Sugar Cookies Recipe
Garnishes
To further enhance these cookies, consider sprinkling a pinch of toasted coconut flakes or a light dusting of powdered sugar just before serving. These garnishes add texture and an extra touch of tropical sweetness, elevating your Pineapple Upside Sugar Cookies Recipe to something truly special.
Side Dishes
These cookies pair wonderfully with a tall glass of cold milk, a cup of hot tea, or even freshly brewed coffee. Their tropical flavors offer a refreshing contrast to warm beverages, making them a perfect afternoon pick-me-up or after-dinner delight.
Creative Ways to Present
For a memorable presentation, arrange the cookies on a bright, tropical-patterned platter or a rustic wooden board. Adding fresh pineapple wedges and cherries around the tray will complement the theme beautifully. You can also stack them in small towers or place each cookie in decorative cupcake liners for an inviting, festive look.
Make Ahead and Storage
Storing Leftovers
If you find yourself with leftover Pineapple Upside Sugar Cookies Recipe treats, store them in an airtight container at room temperature for up to 3 days. This keeps the cookies soft and the toppings flavorful without drying out or becoming tough.
Freezing
For longer storage, freeze cooled cookies individually wrapped in plastic wrap and placed inside a sealed freezer bag. They freeze beautifully for up to 2 months. When ready to enjoy, simply thaw at room temperature—no need for reheating unless you want a warm treat.
Reheating
If you prefer your Pineapple Upside Sugar Cookies Recipe warm, heat them gently in a preheated oven at 300°F (150°C) for about 5 minutes, or microwave for 10 to 15 seconds. This revives that fresh-baked softness and enhances the gooey, caramelized topping.
FAQs
Can I use fresh pineapple instead of canned?
Absolutely! Fresh pineapple slices can be used if you prefer a less sweet, slightly tart flavor. Just make sure to drain them well and pat dry to avoid excess moisture affecting the cookie dough.
What if I don’t have a mini round cake pan?
No worries. You can use a mini muffin pan or even a standard muffin pan, though your cookies will be a bit larger. Adjust the dough amount accordingly and keep an eye on baking time to ensure they bake evenly.
Can I make these cookies vegan?
While traditional recipes call for butter and eggs, you can experiment with vegan butter substitutes and flax eggs. Keep in mind that texture might differ slightly, but the pineapple and brown sugar topping will still shine.
How sweet are these cookies?
These Pineapple Upside Sugar Cookies Recipe treats strike a balanced sweetness thanks to the brown sugar caramel base and juicy fruit on top. They’re sweet but not overpowering, perfect if you enjoy a candy-like fruit accent without overload.
Is sour cream necessary in the dough?
Sour cream adds moisture and tenderness that really elevates the cookie’s texture. You can substitute with Greek yogurt in equal amounts if preferred, but skipping it altogether may result in drier cookies.
Final Thoughts
This Pineapple Upside Sugar Cookies Recipe is one of those delightful finds that injects a little sunshine into your baking routine. It’s easy enough to whip up any day of the week yet impressive enough to wow at gatherings. Give it a try and get ready to fall in love with the tropical flavors and comforting sweetness that make each bite feel like a mini celebration.
Print
Pineapple Upside Sugar Cookies Recipe
- Total Time: 45 minutes
- Yield: 13 cookies 1x
Description
Delightfully sweet and buttery, these Pineapple Upside Down Sugar Cookies combine the classic flavors of a pineapple upside-down cake with the soft, chewy texture of sugar cookies. Each mini cookie features a caramelized pineapple slice and maraschino cherry on the bottom, creating a beautiful presentation and irresistible tropical flavor. Perfect for parties or a special treat.
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). Lightly grease a mini round cake pan to ensure the cookies release easily after baking.
- Cream Butter and Sugar: In a large mixing bowl, cream together the room temperature butter and granulated sugar until the mixture becomes light and fluffy, which helps create a tender cookie texture.
- Add Wet Ingredients: Beat in the eggs, vanilla extract, and sour cream until everything is well incorporated, resulting in a smooth batter.
- Mix Dry Ingredients: Gradually add in the all-purpose flour, baking powder, cornstarch, and salt. Mix until a dough forms, being careful not to overwork it to keep the cookies soft.
- Prepare Topping Mixture: In a separate bowl, combine the melted butter and packed light brown sugar until smooth. This mixture will create the caramelized effect under the pineapple.
- Layer Toppings in Pan: Spread about 1 tablespoon of the brown sugar and butter mixture into each cavity of the mini cake pan. Place a pineapple slice on top, then position a maraschino cherry in the center of the pineapple.
- Add Cookie Dough: Spoon approximately 3 tablespoons of cookie dough over each pineapple slice, gently pressing it so it fully covers the topping and fills the cavity.
- Bake Cookies: Bake the cookies in the preheated oven for 25 minutes, or until they turn golden brown on top and the edges are set.
- Cool and Remove: Allow the cookies to cool in the pan for 10 minutes to set the caramel. Carefully invert the pan onto wax paper or a cooling rack to release the cookies and let them cool completely before serving.
Notes
- Ensure the butter for the dough is at room temperature for easier creaming with sugar.
- You can substitute sour cream with Greek yogurt for a slight tang and moisture.
- Use a mini round cake pan or mini muffin tin with round cavities for best results.
- Make sure to grease the pan well to prevent sticking of the caramelized sugar and pineapple.
- These cookies store well in an airtight container at room temperature for up to 3 days.
- For extra flavor, sprinkle a little cinnamon in the cookie dough.
- Prep Time: 20 minutes
- Cook Time: 25 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
