If you have a sweet tooth craving something truly special, the Pineapple Upside Sugar Cookies Recipe is like a tropical vacation in every bite. These delightful cookies combine the classic favorite of pineapple upside-down cake with the addictively soft and chewy texture of sugar cookies. Imagine the juicy sweetness of pineapple rings topped with a bright maraschino cherry, all nestled beneath a tender cookie dough that bakes up golden and irresistible. This recipe takes simple pantry staples and transforms them into a dessert that feels festive, nostalgic, and fresh all at once.
Ingredients You’ll Need
These ingredients are straightforward but thoughtfully chosen to bring texture, moisture, and flavor harmony to your Pineapple Upside Sugar Cookies Recipe. Each item plays a crucial role, from the richness of butter to the tang of sour cream that keeps the cookies soft and tender.
- 1 cup butter (room temperature): Provides creaminess and a tender crumb perfect for sugar cookies.
- 1 ½ cups granulated sugar: Sweetens the dough and helps achieve a light, fluffy texture.
- 2 eggs: Bind the dough and add richness for a satisfying bite.
- 2 teaspoons vanilla extract: Adds warm, aromatic notes that enhance all the other flavors.
- ½ cup sour cream: Delivers moisture and a slight tang, keeping the cookies soft and flavorful.
- 3 cups all-purpose flour: Forms the structure of the cookies, making them sturdy yet tender.
- 1 teaspoon baking powder: Leavens the dough just enough for a light texture.
- 1 teaspoon cornstarch: Helps create a delicate, tender cookie crumb.
- ½ teaspoon salt: Balances the sweetness and enhances overall flavor.
- 13 canned pineapple slices: The star of the show, delivering juicy tropical sweetness in every cookie.
- 13 maraschino cherries: Adds a pop of color and a classic pineapple upside-down charm.
- ½ cup melted butter: Combines with brown sugar for a sticky, caramel-like base in each cookie well.
- 1 cup packed light brown sugar: Brings rich, caramel flavor to complement the pineapple and cherries.
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) and lightly greasing a mini round cake pan. This ensures the cookies release easily after baking and helps the buttery, sugary base caramelize perfectly.
Step 2: Cream Butter and Sugar
In a large mixing bowl, beat together the room-temperature butter and granulated sugar until the mixture is soft, smooth, and fluffy. This step is key for a light texture as it incorporates air into the dough.
Step 3: Add Wet Ingredients
Beat in the eggs one at a time, followed by the vanilla extract and sour cream. The sour cream adds moisture while the eggs provide richness and binding power.
Step 4: Mix in Dry Ingredients
Gradually add in the all-purpose flour, baking powder, cornstarch, and salt. Mix just until you have a smooth dough—overmixing can toughen your cookies, so take care to stop as soon as everything is combined.
Step 5: Prepare the Sticky Base
In a separate bowl, whisk together the melted butter and light brown sugar until smooth. This mixture will create that luscious caramelized bottom, reminiscent of pineapple upside-down cake.
Step 6: Assemble the Cookies
Spread about one tablespoon of the brown sugar and butter mixture into each cavity of your mini cake pan. Place one pineapple slice on top, then gently press a maraschino cherry into the center of each pineapple ring.
Step 7: Top with Cookie Dough
Spoon approximately three tablespoons of dough over each pineapple slice, pressing down gently to cover the fruit evenly without squeezing out the juices.
Step 8: Bake to Golden Perfection
Bake the assembled cookies for about 25 minutes or until golden brown around the edges. Let them cool in the pan for 10 minutes before carefully turning them out onto wax paper to cool completely. This cooling step helps the sticky caramel base set just right.
How to Serve Pineapple Upside Sugar Cookies Recipe
Garnishes
These cookies are stunning on their own, but you can jazz them up with a light dusting of powdered sugar or a drizzle of vanilla glaze for that extra sweet touch. A sprinkle of toasted coconut flakes will add tropical flair and a lovely texture contrast that echoes the pineapple theme.
Side Dishes
Serve these cookies alongside a scoop of creamy vanilla ice cream or a dollop of whipped cream for a simple yet indulgent dessert pairing. They also pair wonderfully with a hot cup of tea or coffee, making your cozy moments extra special.
Creative Ways to Present
Try serving these cookies as part of a dessert platter featuring tropical fruits like mangoes and kiwi for a vibrant spread. For parties, place the cookies on decorative doilies or small cake stands to showcase their charming pineapple crowns.
Make Ahead and Storage
Storing Leftovers
Once cooled completely, store leftover Pineapple Upside Sugar Cookies in an airtight container at room temperature. They will stay fresh and chewy for up to 4 days, perfect for enjoying throughout the week.
Freezing
You can freeze these cookies by wrapping each one individually in plastic wrap, then placing them in a freezer-safe container or bag. They keep beautifully for up to 2 months. Just thaw at room temperature before serving.
Reheating
Warm the cookies slightly in a microwave for 10 to 15 seconds to revive their softness and the luscious caramel notes. Be sure not to overheat or they may dry out.
FAQs
Can I use fresh pineapple instead of canned?
Fresh pineapple can definitely be used, but make sure to slice it thinly and remove excess juice so your cookie dough doesn’t get too wet. Canned pineapple slices are more consistent and already soften beautifully in the oven.
What can I substitute for sour cream?
If you don’t have sour cream on hand, plain Greek yogurt or crème fraîche work well as substitutes. They provide similar moisture and tanginess that keeps the cookies tender.
Why do I need cornstarch in the dough?
Cornstarch helps create a soft, delicate texture by tenderizing the cookies, so they don’t turn out tough or dense. It’s a small ingredient but makes a big difference.
Can I make these cookies without the maraschino cherries?
Of course! While the maraschino cherry adds classic pineapple upside-down style and a pop of color, you can swap it out for a fresh blueberry, a small piece of dried fruit, or leave the topping as just pineapple.
How do I prevent the cookies from sticking to the pan?
Greasing the mini cake pan well is essential to easily release the cookies after baking. You can use butter, non-stick spray, or even line the cavities with parchment paper rounds if you want to be extra cautious.
Final Thoughts
The Pineapple Upside Sugar Cookies Recipe is a fun and delightful twist on two beloved desserts rolled into one golden, fruity bite. I can’t wait for you to give this recipe a try and add a little sunshine to your cookie jar or party platter. Once you taste that caramelized pineapple under soft, chewy cookie dough, I’m sure it will become a favorite you return to again and again.
Print
Pineapple Upside Sugar Cookies Recipe
- Prep Time: 20 minutes
- Cook Time: 25 minutes
- Total Time: 45 minutes
- Yield: 13 cookies
- Category: Dessert
- Method: Baking
- Cuisine: American
Description
These Pineapple Upside Sugar Cookies are a delightful twist on the classic pineapple upside-down cake, featuring soft and buttery sugar cookie dough layered over caramelized brown sugar and pineapple slices with cherries. Perfectly baked in a mini round cake pan, these cookies offer a tropical flavor with a tender texture that’s sure to please any sweet tooth.
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 prevent sticking and ensure easy removal of the cookies.
- Cream Butter and Sugar: In a large mixing bowl, cream together the room temperature butter and granulated sugar until the mixture is light and fluffy, which helps create a tender texture in the cookies.
- Add Wet Ingredients: Mix in the eggs, vanilla extract, and sour cream thoroughly, ensuring the mixture is smooth and well combined for a rich, moist dough.
- Combine Dry Ingredients: Gradually add the all-purpose flour, baking powder, cornstarch, and salt into the wet mixture, mixing until a soft cookie dough forms.
- Prepare Brown Sugar Mixture: In a separate bowl, combine the melted butter and packed light brown sugar, mixing well until they are evenly blended for a caramel-like topping.
- Assemble Cookies: Spread 1 tablespoon of the brown sugar and butter mixture evenly into each cavity of the mini cake pan. Place a pineapple slice on top of the brown sugar layer, then place a maraschino cherry in the center of each pineapple slice.
- Add Cookie Dough: Spoon about 3 tablespoons of cookie dough onto each pineapple slice, gently pressing to cover the fruit and topping completely with dough.
- Bake: Bake the cookies in the preheated oven for 25 minutes or until they turn golden brown on top, indicating they are fully cooked.
- Cool and Serve: Allow the cookies to cool in the pan for 10 minutes, then carefully turn them out onto wax paper to cool completely before serving.
Notes
- You can use fresh pineapple slices if preferred, but canned works best for consistent sweetness and texture.
- Make sure the butter is at room temperature to help with proper creaming and dough consistency.
- Allow the cookies to cool completely to let the topping set and avoid breaking when removing from the pan.
- These cookies are best served within 2-3 days stored in an airtight container at room temperature.
