If you adore the tropical charm of pineapple with the comforting sweetness of sugar cookies, you are in for a treat with this Pineapple Upside Sugar Cookies Recipe. These delightful cookies cleverly transform the classic pineapple upside-down cake into a fun, handheld dessert that’s bursting with juicy pineapple, vibrant maraschino cherries, and golden, buttery sugar cookie tops. Every bite offers a perfect balance of tangy fruit and soft, tender cookies that will have you reaching for more. Trust me, this recipe is pure sunshine on a plate and perfect for any occasion where you want to impress with minimal effort and maximum flavor.
Ingredients You’ll Need
It’s amazing how just a handful of simple ingredients can come together to create something so delicious. Each ingredient plays a key role in the success of this Pineapple Upside Sugar Cookies Recipe, contributing flavors and textures that blend harmoniously.
- 16.5-ounce package refrigerated sugar cookie dough: This forms the tender, buttery base and top that holds everything together beautifully.
- 20-ounce can pineapple slices (drained and patted dry): The star of the dish that adds a sweet-tart juiciness and tropical flair—drying is crucial for crispness.
- 12 maraschino cherries (halved): For that classic pop of color and a subtle burst of sweetness in the center of each pineapple ring.
- ¼ cup packed brown sugar: Adding caramel-like richness that perfectly complements the pineapple’s brightness.
- 2 tablespoons unsalted butter (melted): This binds with the brown sugar to create a luscious, sticky base at the bottom of each cookie.
- Optional whipped cream for topping: The light cloud of creaminess that elevates these cookies into a true indulgence.
How to Make Pineapple Upside Sugar Cookies Recipe
Step 1: Prepare Your Oven and Muffin Tin
Start by preheating your oven to 350°F and lightly greasing a 12-cup muffin tin. This simple prep ensures that each cookie will come out easily without sticking, giving you that perfect golden finish.
Step 2: Create the Caramelized Base
In a small bowl, stir together the melted butter and brown sugar until they form a smooth mixture. Spoon about one teaspoon of this mixture into the bottom of each muffin cup. This layer will melt and caramelize during baking, creating a dreamy sticky-sweet base that perfectly contrasts the soft cookie topping.
Step 3: Add the Pineapple and Cherry
Next, carefully place one pineapple slice into each muffin cup, trimming edges if necessary to fit the cup snugly. Nestle half a maraschino cherry right in the center of each pineapple ring. This bright jewel in the middle not only looks stunning but adds a classic burst of flavor that brings nostalgia and fun.
Step 4: Top with Sugar Cookie Dough
Slice your sugar cookie dough into 12 evenly sized rounds, then gently press one atop each pineapple slice, making sure to cover the fruit completely without squashing it. This gentle pressing will help the dough bake evenly and lock in the pineapple’s juices, producing a tender and flavorful cookie.
Step 5: Bake and Cool
Bake your cookies for 16 to 18 minutes until the cookie tops turn a gorgeous golden brown. Once baked, let them cool in the muffin tin for about 5 to 7 minutes—this resting time helps the caramel set slightly for cleaner removal. Then carefully run a knife around the edges and invert each cup onto a wire rack or tray to reveal your stunning pineapple upside-down cookie creation.
How to Serve Pineapple Upside Sugar Cookies Recipe
Garnishes
These cookies are lovely on their own, but if you want to add an extra touch of charm, a dollop of whipped cream on top works wonders. The creamy texture balances the sweet and tangy flavors, making these cookies irresistible.
Side Dishes
Pair your Pineapple Upside Sugar Cookies Recipe with a light cup of tea or fresh fruit salad for a refreshing contrast. The tropical notes in the cookies naturally complement fresh berries or even a citrusy sorbet for a casual dessert spread.
Creative Ways to Present
For gatherings, present these cookies on a rustic wooden tray lined with banana leaves to enhance their tropical vibe. You can also drizzle a bit of honey or sprinkle toasted coconut flakes on top to introduce new textures and flavors that will wow your guests.
Make Ahead and Storage
Storing Leftovers
Leftover pineapple upside sugar cookies can be stored in an airtight container at room temperature for up to three days. This keeps their moisture locked in without making them soggy, so they stay just as delightful as when freshly baked.
Freezing
If you want to save them longer, freezing is an excellent option. Wrap each cookie individually in plastic wrap, then place them in a freezer bag or container. They freeze well for up to two months and thaw quickly at room temperature.
Reheating
To regain that freshly baked warmth and aroma, pop the cookies in a 300°F oven for about 5-7 minutes or microwave briefly on a low setting. This gentle reheating refreshes the buttery cookie and caramelized pineapple for another heavenly bite.
FAQs
Can I use homemade sugar cookie dough for this recipe?
Absolutely! While refrigerated dough makes this Pineapple Upside Sugar Cookies Recipe quick and convenient, homemade sugar cookie dough works beautifully and adds that extra personal touch for flavor and texture.
How important is it to dry the pineapple slices?
Very important! Drying the pineapple slices well prevents excess moisture from making the cookies soggy and helps achieve that perfect caramelization at the base of each cookie.
Can I substitute fresh pineapple for canned?
Yes, you can, but be sure to slice it thinly and pat it dry thoroughly. Fresh pineapple can add wonderful brightness but also carries more moisture, so drying is essential for great results.
What is the best way to remove the cookies from the muffin tin?
Run a small knife around each cookie’s edge to loosen it, then gently invert the muffin tin onto a wire rack or tray. This lets the caramelized bottom become the top and reveals the pineapple and cherry beautifully.
Can these cookies be made gluten-free or vegan?
With some ingredient swaps, yes! Use gluten-free sugar cookie dough and check the pineapple and cherries for any additives. Vegan butter or margarine can replace butter, but note that textures may vary slightly.
Final Thoughts
Making the Pineapple Upside Sugar Cookies Recipe is like holding a little bite of tropical sunshine in your hand. It’s quick, fun, and incredibly satisfying, blending nostalgic flavors with a playful twist. Whether you’re baking for family, friends, or just because you deserve a sweet treat, these cookies are sure to brighten your day and create smiles all around. Give them a try—you’ll wonder why you didn’t make them sooner!
Print
Pineapple Upside Sugar Cookies Recipe
- Prep Time: 10 minutes
- Cook Time: 18 minutes
- Total Time: 30 minutes
- Yield: 12 cookies
- Category: Dessert
- Method: Baking
- Cuisine: American
- Diet: Vegetarian
Description
These Pineapple Upside Sugar Cookies combine the sweet, tropical flavors of pineapple and maraschino cherries with soft, buttery sugar cookie dough for a delightful twist on the classic pineapple upside-down cake. Perfect as a fun dessert or festive treat, they bake up golden and tender with a luscious caramelized brown sugar base.
Ingredients
Cookie Base
- 1 (16.5-ounce) package refrigerated sugar cookie dough
Fruit Topping
- 1 (20-ounce) can pineapple slices (drained and patted dry)
- 12 maraschino cherries (halved)
Brown Sugar Mixture
- ¼ cup packed brown sugar
- 2 tablespoons unsalted butter (melted)
Optional
- Whipped cream for topping
Instructions
- Prepare the Muffin Tin: Preheat your oven to 350°F (175°C) and lightly grease a 12-cup muffin tin to prevent sticking and to help with easy removal of the cookies.
- Make the Brown Sugar Base: In a small bowl, mix the melted unsalted butter with the packed brown sugar until well combined. Spoon about 1 teaspoon of this mixture evenly into the bottom of each muffin cup, forming a sweet caramel base.
- Add Pineapple and Cherry: Place one pineapple slice into each muffin cup over the brown sugar mixture. Trim the slices if needed to fit the muffin cup perfectly. Then, place half of a maraschino cherry in the center of each pineapple slice, pressing slightly to secure.
- Top with Cookie Dough: Slice the refrigerated sugar cookie dough into 12 even rounds. Place one round on top of each pineapple slice in the muffin cups and gently press down to cover the fruit evenly.
- Bake the Cookies: Bake the assembled cookies in the preheated oven for 16–18 minutes or until the cookie tops turn golden brown and are cooked through.
- Cool and Unmold: Allow the cookies to cool in the muffin tin for 5–7 minutes. Run a knife gently around the edges of each cookie to loosen them, then carefully invert the muffin tin onto a wire rack or tray to release the pineapple-topped cookies.
- Serve: Serve the pineapple upside sugar cookies warm or at room temperature. Optionally, add a dollop of whipped cream on top for extra indulgence.
Notes
- Ensure the pineapple slices are thoroughly drained and patted dry with paper towels to prevent sogginess in the cookies.
- For a homemade touch, feel free to use your favorite sugar cookie dough recipe instead of store-bought dough.
- Letting cookies cool slightly before unmolding helps them keep their shape and prevents breaking.
