Pineapple Upside Sugar Cookies Recipe
A burst of tropical flavor meets classic Americana in this irresistible Pineapple Upside Sugar Cookies Recipe! Imagine the best parts of a pineapple upside-down cake—golden pineapple, bright red cherries, and buttery caramel—all cozied up into a soft, chewy sugar cookie. They’re not only a joy to look at, but every bite is packed with juicy fruit and warm vanilla flavor. If you love a quick, impressive dessert that’s guaranteed to earn you recipe requests at every gathering, this is one you won’t want to miss.
Ingredients You’ll Need
This Pineapple Upside Sugar Cookies Recipe comes together with just a handful of simple pantry staples and a few classic fruit toppings. Every ingredient has a delicious job to do: from the sugar cookie dough (hello, convenience!) to the sweet-tart pineapple and cheerful cherries, each addition brings its own unique character and color to the cookies.
- Refrigerated sugar cookie dough (1 roll, 16.5 oz): The shortcut star that delivers a soft, chewy cookie texture with minimal effort.
- Crushed pineapple (1 cup, drained): Adds tropical sweetness and moisture; be sure to drain well for the best results.
- Light brown sugar (½ cup): Gives the “upside-down” caramel effect and blends beautifully with the juicy pineapple.
- Unsalted butter (2 tablespoons, melted): Helps caramelize the fruit for that classic upside-down taste.
- Maraschino cherries (12, halved): For that signature pop of color and a sweet, playful finish in each cookie.
- Cinnamon (¼ teaspoon, optional): A hint of spice if you want a subtle warmth that pairs nicely with the fruit.
How to Make Pineapple Upside Sugar Cookies Recipe
Step 1: Prep Your Oven and Muffin Tin
Preheat your oven to 350°F (175°C), setting the stage for golden, delicious cookies. Grab a standard 12-cup muffin tin and give it a light greasing—this makes the cookies come out flawlessly after baking, ensuring you capture all the pineapple goodness underneath.
Step 2: Mix the Pineapple Topping
In a small bowl, stir together the well-drained crushed pineapple, light brown sugar, melted butter, and a sprinkle of cinnamon if you’d like a touch of spice. This luscious mixture is what makes every bite of the Pineapple Upside Sugar Cookies Recipe taste like a sunny-day treat.
Step 3: Fill Each Muffin Cup
Spoon about 1 tablespoon of the pineapple mixture into the bottom of each muffin cup. This fruity base sets up the classic “upside down” look, and keeps the cookie tops juicy and flavorful. Next, press a maraschino cherry half (cut side up) right into the center of each muffin cup—this is the colorful signature you’ll see when you flip them out!
Step 4: Add the Sugar Cookie Dough
Take your sugar cookie dough roll and slice it into 12 equal pieces. Gently flatten and press one portion over the pineapple mixture in each cup, spreading it slightly so it covers everything up. Don’t worry if it’s not perfect; the dough will spread and form a beautiful “lid” as it bakes.
Step 5: Bake and Release
Slide your muffin tin into the oven and bake for 12–15 minutes, or until the cookie tops are turning a lovely golden brown. Let the cookies rest in the pan for a quick 5 minutes—this helps the caramelized fruit to set. Then, carefully run a knife around each cookie and invert the whole muffin tin over a wire rack. Give it a gentle tap to release the Pineapple Upside Sugar Cookies Recipe in all their pretty, pineapple-topped glory!
Step 6: Serve and Enjoy
Enjoy your cookies warm for a gooey treat, or at room temperature for an easy grab-and-go dessert. No matter how you serve them, these are sure to be a showstopper at any get-together.
How to Serve Pineapple Upside Sugar Cookies Recipe
Garnishes
To make each cookie even more festive, dust with a light sprinkle of powdered sugar right before serving, or perch a bit of lime zest on the cherry for a twist of color and flavor. A tiny sprig of mint would take these cookies straight from homey to high-tea chic!
Side Dishes
Pair these tropical treats with a scoop of vanilla ice cream, a dollop of whipped cream, or some coconut sorbet. For coffee or tea time, serve alongside a platter of fresh sliced mango or berries for a refreshing fruit contrast that lets the pineapple flavors sing.
Creative Ways to Present
Arrange your Pineapple Upside Sugar Cookies Recipe on a tiered dessert stand to show off each jewel-like cherry center. For a party, serve each cookie in a decorative cupcake liner, or box them up as edible gifts with fun tropical-inspired wrappers and ribbon. These cookies make an unforgettable parting favor at picnics, showers, or brunches too!
Make Ahead and Storage
Storing Leftovers
If you happen to have any cookies left (good luck!), store them in an airtight container at room temperature. The Pineapple Upside Sugar Cookies Recipe will stay soft and fruity for up to two days, but they’re tastiest the same day you bake them due to the fresh fruit topping.
Freezing
For longer storage, you can freeze the finished cookies once they cool completely. Layer them between sheets of parchment paper in a freezer-safe container. When ready to enjoy, just set them out at room temperature for about 30 minutes. Avoid microwaving to keep the fruit topping in place.
Reheating
If you love your cookies slightly warm, reheat them in a 300°F oven for 2-3 minutes. This refreshes the texture and brings back that just-baked aroma, making the Pineapple Upside Sugar Cookies Recipe extra tempting!
FAQs
Can I use homemade sugar cookie dough instead of store-bought?
Absolutely! If you’ve got a signature sugar cookie dough recipe, feel free to swap it in—just aim for a soft, spreadable dough so the cookies bake up tender and chewy. The Pineapple Upside Sugar Cookies Recipe is very forgiving with homemade touches.
How do I make sure the cookies don’t stick to the muffin tin?
A generous greasing of your muffin tin is the best defense. You can also use a nonstick spray or even line the bottoms with parchment circles. Letting the cookies rest for 5 minutes after baking gives the fruit mixture time to set and helps with a cleaner release.
Can I substitute fresh pineapple for canned?
Definitely! Fresh pineapple gives a vibrant tang, just be sure to finely chop and drain it well to avoid extra moisture. The Pineapple Upside Sugar Cookies Recipe works great with either one, so use what you have.
How far in advance can I prepare these cookies?
You can prepare the pineapple-cherry mixture and slice the cookie dough up to a day ahead. Assemble and bake the cookies the day you plan to serve for the freshest, most vibrant presentation. If needed, baked cookies can be stored and enjoyed for two days.
What’s the best way to transport these cookies for a party?
Once cooled, place each cookie in a cupcake liner for easy handling, then layer them (separated by wax paper) in a sturdy container. The Pineapple Upside Sugar Cookies Recipe holds up well on road trips, potlucks, or packed up for an afternoon picnic!
Final Thoughts
Ready for a bite of sunshine? The Pineapple Upside Sugar Cookies Recipe delivers all the cheerful flavor and wow factor of a classic upside-down cake, in a fun-sized, fuss-free package. Share with friends or whip up a batch just for you—you won’t believe how quickly they disappear!
Print
Pineapple Upside Sugar Cookies Recipe
- Total Time: 25 minutes
- Yield: 12 cookies 1x
- Diet: Vegetarian
Description
Indulge in these delightful Pineapple Upside Sugar Cookies that combine the classic flavors of pineapple upside-down cake with the simplicity of sugar cookies. These individual treats are perfect for a sweet tropical twist.
Ingredients
For the cookies:
- 1 roll (16.5 oz) refrigerated sugar cookie dough
For the pineapple topping:
- 1 cup crushed pineapple (drained)
- ½ cup light brown sugar
- 2 tablespoons unsalted butter, melted
- 12 maraschino cherries, halved
- Optional: ¼ teaspoon cinnamon for added flavor
Instructions
- Preheat the oven: Preheat oven to 350°F (175°C). Grease a standard 12-cup muffin tin.
- Prepare the pineapple topping: In a small bowl, mix the drained crushed pineapple, brown sugar, melted butter, and cinnamon if using. Spoon about 1 tablespoon of the mixture into each muffin cup. Place a cherry half (cut side up) in the center of each cup.
- Assemble the cookies: Slice the sugar cookie dough into 12 equal portions. Gently press one portion over each pineapple mixture, spreading slightly to cover.
- Bake: Bake for 12–15 minutes or until the cookie tops are golden brown.
- Cool and serve: Let the cookies cool in the pan for 5 minutes, then run a knife around the edges and carefully invert the muffin tin onto a wire rack or tray to release the cookies. Serve warm or at room temperature.
Notes
- Make sure the pineapple is well drained to prevent soggy bottoms.
- Best served the day of baking but can be stored in an airtight container for up to 2 days.
- Prep Time: 10 minutes
- Cook Time: 15 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
Nutrition
- Serving Size: 1 cookie
- Calories: 190
- Sugar: 18g
- Sodium: 140mg
- Fat: 7g
- Saturated Fat: 3g
- Unsaturated Fat: 3g
- Trans Fat: 0g
- Carbohydrates: 30g
- Fiber: 0g
- Protein: 1g
- Cholesterol: 10mg
