Christmas Pineapple Upside-Down Sugar Cookies Recipe
Bring a slice of holiday joy to your cookie platter this year with Christmas Pineapple Upside-Down Sugar Cookies! These little gems combine the nostalgic sparkle of pineapple upside-down cake with the beloved buttery chew of sugar cookies, all bundled up in an adorable handheld treat. Each bite is a playful mix of brown sugar caramel, tangy pineapple, and bursts of cherry atop a soft, cinnamon-kissed base. With their jewel-like toppings and irresistible flavor, it’s impossible not to smile — and to reach for seconds!
Ingredients You’ll Need
Ingredients You’ll Need
Just a handful of everyday ingredients is all it takes to build these merry showstoppers. Each element serves a special purpose, from tenderizing the cookies to giving them their signature tropical twist and ruby-red holiday sparkle.
- Unsalted butter (½ cup, softened): This gives the cookies their rich flavor and soft, chewy texture—make sure it’s room temperature for easy creaming.
- Granulated sugar (½ cup): Essential for sweetness and a perfect sugar cookie crumb.
- Packed brown sugar (¼ cup, plus ⅓ cup for topping): Deepens the flavor and delivers that irresistible caramel touch both inside and on top of the cookies.
- Large egg (1): Binds everything together and ensures a tender dough that holds its shape after baking.
- Vanilla extract (1 teaspoon): Adds warmth and rounds out the flavors.
- All-purpose flour (1½ cups): The backbone of your cookie, providing structure without making the cookies dense.
- Baking powder (½ teaspoon): Helps the cookies rise to just the right thickness.
- Salt (¼ teaspoon): Don’t skip it—salt balances all the sweet and bright flavors.
- Ground cinnamon (½ teaspoon): Lends a cozy, holiday aroma that makes each bite extra festive.
- Pineapple slices (1 20-oz can, cut small): Drain these well and chop them into bite-sized pops of flavor and sunshine.
- Maraschino cherries (⅓ cup, halved): For that classic upside-down cake look and a touch of sweetness and color—use both red and green for extra Christmas pizzazz.
- Melted butter (2 tablespoons): Combined with brown sugar to create that gooey caramel halo on top.
How to Make Christmas Pineapple Upside-Down Sugar Cookies
Step 1: Prepare Your Muffin Tin
Begin by preheating your oven to 350°F and generously spraying a 12-cup muffin tin with nonstick cooking spray. This quick step ensures those glimmering fruit-topped cookies pop out effortlessly, preserving their picture-perfect tops. Setting up your pan makes the assembly process a breeze and promises beautiful, bakery-style results.
Step 2: Make the Caramel Topping and Fruit Layer
In a small bowl, stir together 2 tablespoons of melted butter with 1/3 cup of brown sugar. Drop about 1 teaspoon of this mixture into the bottom of each muffin cup. Next, nestle 1 or 2 little pineapple pieces and half a maraschino cherry (red or green, for full holiday flair) on top of the brown sugar—this little arrangement will greet you upside-down once baked.
Step 3: Prepare the Sugar Cookie Dough
In a medium mixing bowl, cream the softened butter, granulated sugar, and 1/4 cup brown sugar together until the mixture is light and fluffy. This step really matters, as it gives your cookies that soft, tender bite. Beat in the egg and vanilla extract until smooth. In a separate bowl, whisk together flour, baking powder, salt, and cinnamon. Gradually blend the dry ingredients into the wet, mixing just until a soft, slightly sticky dough forms—don’t overmix, or the cookies will toughen.
Step 4: Assemble and Bake
Scoop about 1½ tablespoons of dough into each muffin cup, gently pressing the dough so it covers the fruit and caramel layer completely. Slide the tray into your preheated oven and bake for 15 to 18 minutes, just until the edges turn golden and you smell that irresistible caramel-cinnamon aroma wafting through your kitchen.
Step 5: Cool and Invert
Let the cookies cool in the muffin tin for 5 minutes—they set up just enough to handle but are still soft and luscious. Carefully run a knife around the edge of each cookie, then invert the pan onto a wire rack so the fruit side is up. Don’t worry if a little fruit sticks; just nudge it back into place. Allow to cool completely before serving.
How to Serve Christmas Pineapple Upside-Down Sugar Cookies
Garnishes
To add a little extra twinkle to your Christmas Pineapple Upside-Down Sugar Cookies, consider a dusting of powdered sugar “snow,” a glistening brush of apricot jam for shine, or even a sprinkle of festive holiday sprinkles. Each small touch makes these cookies shimmer on your holiday platter!
Side Dishes
These cookies are the ultimate festive treat, but they pair beautifully with simple sides like a scoop of vanilla ice cream, a mug of creamy hot chocolate, or a platter of citrusy fruit salad. The fresh, cool flavors balance the sweetness and make for a merry cookie exchange or a cozy dessert spread.
Creative Ways to Present
For an extra-special touch, line a holiday tin with parchment, stack the cookies upside-down (fruit side up!), and tie it with a bright ribbon for a show-stopping homemade gift. Arrange them on a cake stand with sprigs of fresh rosemary “pine” for centerpiece-worthy presentation, or nestle them into individual cupcake wrappers for grab-and-go holiday nibbling.
Make Ahead and Storage
Storing Leftovers
These Christmas Pineapple Upside-Down Sugar Cookies are irresistibly soft and moist, but they do best if enjoyed within two days. Tuck any extras into an airtight container and keep at room temperature—just make sure the caramel and fruit are fully cooled to prevent any sogginess.
Freezing
You can freeze these cookies for longer storage! After cooling, place the cookies in a single layer on a parchment-lined tray and freeze until solid. Then transfer to a freezer-friendly bag or container with parchment between layers. They’ll keep beautifully for up to 2 months—just thaw at room temperature before serving.
Reheating
While these cookies are delicious at room temperature, if you prefer a just-baked warmth, pop them in a 300°F oven for 5 minutes or microwave in 10-second bursts. This refreshes the cookie and helps the caramel topping glisten again—like a holiday treat straight from the oven!
FAQs
Can I use fresh pineapple instead of canned?
Absolutely! Just chop the fresh pineapple into small pieces and pat them dry with a paper towel before using—this helps avoid extra moisture that might make the cookie base soggy.
How do I keep the cookies from sticking to the muffin tin?
Spraying the tin generously with nonstick spray is key, and letting the cookies rest a few minutes before inverting helps them release cleanly. Running a thin knife around each edge also makes unmolding a snap.
Can I make the dough ahead of time?
Yes! You can prepare the sugar cookie dough up to a day in advance and store it, tightly covered, in the refrigerator. Let it sit at room temperature for 10 minutes before assembling the cookies for easier scooping.
Do these freeze well after baking?
They freeze wonderfully. Simply chill them completely, layer with parchment, and store in a freezer-safe container. Thaw at room temperature and enjoy, or gently warm before serving to refresh the caramel topping.
Can I double the recipe for a party?
Definitely! Just double all ingredients and bake in batches if needed. These cookies are perfect for sharing, so don’t be surprised if they disappear fast—maybe stash a few for yourself!
Final Thoughts
If you’re looking to bring both tradition and sparkle to your holiday table, Christmas Pineapple Upside-Down Sugar Cookies are just the cheerful treat you need. They’re easy to make, a joy to share, and sure to inspire smiles with every festive, fruity bite. Give them a whirl and watch these cookies become your new holiday favorite!
Print
Christmas Pineapple Upside-Down Sugar Cookies Recipe
- Total Time: 38 minutes
- Yield: 12 cookies 1x
- Diet: Vegetarian
Description
These Christmas Pineapple Upside-Down Sugar Cookies are a delightful twist on the classic upside-down cake, perfect for the holiday season. With a buttery sugar cookie base, topped with sweet pineapple and cherries, these festive treats are sure to impress your guests.
Ingredients
For the Cookie Dough:
- 1/2 cup unsalted butter (softened)
- 1/2 cup granulated sugar
- 1/4 cup brown sugar (packed)
- 1 large egg
- 1 teaspoon vanilla extract
- 1 1/2 cups all-purpose flour
- 1/2 teaspoon baking powder
- 1/4 teaspoon salt
- 1/2 teaspoon ground cinnamon
For the Topping:
- 1 (20 oz) can pineapple slices (cut into small pieces)
- 1/3 cup maraschino cherries (halved)
- 2 tablespoons butter (melted)
- 1/3 cup brown sugar (for topping)
Instructions
- Preheat the oven: Preheat the oven to 350°F. Spray a muffin tin generously with nonstick cooking spray.
- Prepare the topping: In a small bowl, stir together the 2 tablespoons of melted butter and 1/3 cup brown sugar. Spoon about 1 teaspoon of the mixture into the bottom of each muffin cup, then place pineapple and cherries on top.
- Make the dough: Cream together the butter and sugars, beat in the egg and vanilla. In another bowl, whisk together the dry ingredients. Gradually mix the dry ingredients into the wet mixture until a soft dough forms.
- Assemble and bake: Scoop dough into each muffin cup over the fruit layer. Bake for 15 to 18 minutes until golden. Cool for 5 minutes, then invert onto a wire rack to release. Cool completely.
Notes
- For extra holiday flair, use green and red maraschino cherries.
- Make sure to drain the pineapple and cherries well to prevent excess moisture.
- Best served the same day but can be stored in an airtight container for up to 2 days.
- Prep Time: 20 minutes
- Cook Time: 18 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
Nutrition
- Serving Size: 1 cookie
- Calories: 190
- Sugar: 18g
- Sodium: 80mg
- Fat: 8g
- Saturated Fat: 5g
- Unsaturated Fat: 2g
- Trans Fat: 0g
- Carbohydrates: 28g
- Fiber: 0g
- Protein: 2g
- Cholesterol: 30mg
