If you’re looking to sweeten your holiday cookie tray with something playful and bright, you’ll absolutely love these Christmas Pineapple Upside-Down Sugar Cookies. These charming treats combine the classic buttery softness of a sugar cookie with the caramelized fruitiness of pineapple and cherries, all nestled in adorable, single-serve upside-down form. They’re bursting with festive flair, and the jewel-like topping will grab everyone’s attention at your next cookie exchange or holiday gathering. Once you’ve tried this delicious mashup, it might just become a new seasonal tradition!
Ingredients You’ll Need
The magic of Christmas Pineapple Upside-Down Sugar Cookies comes from a handful of simple ingredients. Each one plays an important role: the buttery cookie base is sweet and tender, while the pineapple and cherries give the cookies their signature pop of color and zingy flavor. Here’s what you’ll need and why they matter.
- Unsalted Butter (softened): Brings richness and that classic melt-in-your-mouth texture to the sugar cookie base.
- Granulated Sugar: Delivers sweetness while helping the cookie achieve a touch of crispness around the edges.
- Light Brown Sugar: Adds a hint of caramel flavor—perfect for echoing traditional upside-down cake.
- Large Egg: Binds everything together and contributes to the cookie’s lovely softness.
- Vanilla Extract: Infuses the dough with warm, cozy notes that make every bite irresistible.
- All-Purpose Flour: Provides structure so your cookies hold their shape but remain tender.
- Baking Powder: Gives the cookies a gentle lift for just the right amount of fluffiness.
- Salt: Enhances every flavor and keeps the cookies from tasting flat or overly sweet.
- Crushed Pineapple (drained well): Adds tropical tanginess and juiciness—make sure to drain well so the cookies don’t get soggy.
- Maraschino Cherries (chopped): Offer pops of color and sweet-tart flavor that scream holiday cheer.
- Light Brown Sugar (for topping): Helps create that caramel-like pineapple crown atop each cookie.
- Unsalted Butter (melted, for topping): Ensures the topping is glossy and encourages a golden, buttery finish.
How to Make Christmas Pineapple Upside-Down Sugar Cookies
Step 1: Prepare the Topping & Pan
Start by preheating your oven to 350°F (175°C) so it’s ready when your cookies are. Generously grease a 12-cup muffin tin—this helps the cookies release easily and stay beautiful. In a small bowl, stir together 1/4 cup brown sugar and the melted butter, then spoon a teaspoon of the mixture into each muffin cup. This step mimics that classic upside-down cake caramelization and creates a luscious base for your fruit.
Step 2: Add the Pineapple and Cherries
Next, add a small spoonful of well-drained crushed pineapple right on top of the brown sugar-butter mixture in each cup. Press a few chopped maraschino cherries into the pineapple. This is where you can get creative—make festive patterns or simply scatter the fruit for colorful bursts in every bite. Proper draining here is crucial so your cookies end up perfectly golden and not soggy.
Step 3: Make the Sugar Cookie Dough
In a large mixing bowl, cream together the softened butter, granulated sugar, and remaining 1/4 cup brown sugar until light and fluffy. This step is key for a tender, airy sugar cookie base. Beat in the egg and vanilla extract, mixing until completely smooth and combined. In a separate bowl, whisk together the flour, baking powder, and salt—this keeps the dry ingredients evenly distributed for a perfect bake.
Step 4: Combine Wet and Dry Ingredients
Gradually add the dry ingredients into your wet mixture, stirring gently until just combined. Take care not to overmix; you want your Christmas Pineapple Upside-Down Sugar Cookies to be delicate and soft, not tough. The dough will be thick but still scoopable—that’s exactly what you want.
Step 5: Assemble and Bake
Scoop about 2 tablespoons of cookie dough into each prepared muffin cup, gently pressing it down to cover the fruit and brown sugar topping. Bake in your preheated oven for 12 to 15 minutes. Look for lightly golden edges (and maybe a faint caramel aroma wafting through your kitchen) as your signal they’re ready! Let them cool in the pan for 5 minutes.
Step 6: Unmold and Cool
Run a knife around the edge of each cookie to loosen, then place a wire rack over the pan and quickly invert the cookies out so their beautiful pineapple-cherry topping is on display. Let them cool completely right-side-up on the rack, admiring just how pretty and perfectly portioned each treat is.
How to Serve Christmas Pineapple Upside-Down Sugar Cookies
Garnishes
These cookies look stunning right out of the pan, but to amp up the festive vibe, try sprinkling them with red and green holiday sprinkles or a dusting of powdered sugar. A tiny mint leaf or a fresh cherry on top can add an extra twinkle, making these cookies positively sparkle at the dessert table.
Side Dishes
Pair your Christmas Pineapple Upside-Down Sugar Cookies with creamy vanilla ice cream, a piping hot cup of cocoa, or a bowl of soft whipped cream for dipping. For grown-up gatherings, a fruity punch or spiced tea adds a cozy, complementary note that heightens all those tropical and caramel flavors.
Creative Ways to Present
Pack them in a festive holiday tin layered with parchment for a gorgeous edible gift, or arrange them on a platter in the shape of a wreath for your holiday centerpiece. You can even stack a few and wrap them with a bow for a sweet little favor—these cookies are as delightful to give as they are to eat.
Make Ahead and Storage
Storing Leftovers
Store any leftover Christmas Pineapple Upside-Down Sugar Cookies in an airtight container at room temperature for up to three days. Their flavors intensify and the cookies stay soft—just make sure they’re cool before packing them away to avoid condensation and sogginess.
Freezing
Yes, these cookies freeze beautifully! Place them in a single layer on a baking sheet to freeze solid, then transfer to a zip-top bag or container with parchment between layers. They’ll keep for up to two months—just thaw at room temperature when you’re ready for a taste of the holidays.
Reheating
For that fresh-from-the-oven texture, zap a cookie in the microwave for just 5 to 10 seconds. This will revive the buttery crumb and bring out the juicy fruit topping, making them taste just-baked even days later.
FAQs
Can I use fresh pineapple instead of canned?
Absolutely! Just make sure to chop and drain it thoroughly. Extra moisture from fresh pineapple can make the cookies soggy, so give it a good squeeze before using. The flavor will be a touch brighter and even more refreshing.
Do I need to use muffin tins, or can I bake them on a baking sheet?
The muffin tin really helps create that classic upside-down look and keeps the topping neatly contained. You can try using silicone muffin pans for easier removal, but a regular baking sheet won’t provide the same effect or caramelized edges.
Can I make the dough in advance?
Yes, you can mix up the cookie dough a day in advance. Cover tightly and store in the refrigerator until you’re ready to scoop, assemble, and bake. This is especially handy for busy holiday prep!
How do I prevent the cookies from sticking to the pan?
Generous greasing is your friend. Use nonstick spray or real butter, and don’t forget to loosen the edges with a knife before inverting. If you’re worried, line the bottoms with parchment circles for extra insurance.
Are Christmas Pineapple Upside-Down Sugar Cookies vegetarian?
Yes! The recipe uses no gelatin or animal products besides eggs and dairy, so it fits perfectly into a vegetarian holiday treat spread. For an egg-free version, you could experiment with flaxseed egg substitutes as well.
Final Thoughts
There’s just something magical about the colorful, glistening tops and buttery-soft centers of Christmas Pineapple Upside-Down Sugar Cookies. If you’re itching to add a new, memory-making recipe to your winter baking lineup, these are a joyful and delicious place to start. Gather your ingredients, share them with family and friends, and let the holiday baking fun begin!
Print
Christmas Pineapple Upside-Down Sugar Cookies Recipe
- Total Time: 35 minutes
- Yield: 12 cookies 1x
- Diet: Vegetarian
Description
These Christmas Pineapple Upside-Down Sugar Cookies are a delightful twist on a classic treat, with a tropical flair perfect for the holiday season. Soft, buttery cookies topped with sweet pineapple and cherries, they are sure to be a hit at any festive gathering.
Ingredients
Cookies:
- 1/2 cup unsalted butter (softened)
- 1/2 cup granulated sugar
- 1/4 cup packed light brown sugar
- 1 large egg
- 1 teaspoon vanilla extract
- 1 1/2 cups all-purpose flour
- 1/2 teaspoon baking powder
- 1/4 teaspoon salt
Topping:
- 1/2 cup crushed pineapple (well-drained)
- 1/4 cup maraschino cherries (chopped)
- 1/4 cup packed light brown sugar (for topping)
- 2 tablespoons unsalted butter (melted, for topping)
Instructions
- Preheat the oven and prepare the muffin tin: Preheat the oven to 350°F (175°C) and grease a 12-cup muffin tin.
- Prepare the topping: In a small bowl, mix 1/4 cup brown sugar and melted butter. Spoon a teaspoon into each muffin cup, add crushed pineapple, and cherries.
- Make the cookie dough: Cream butter, granulated sugar, and brown sugar. Add egg and vanilla. In a separate bowl, combine flour, baking powder, and salt. Mix the dry ingredients into the wet ingredients.
- Assemble and bake: Scoop cookie dough into each cup, press down gently. Bake for 12-15 minutes until golden. Cool, then invert onto a wire rack.
Notes
- Ensure the crushed pineapple is well-drained for the best texture.
- Garnish with festive sprinkles for a holiday touch!
- Prep Time: 20 minutes
- Cook Time: 15 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
Nutrition
- Serving Size: 1 cookie
- Calories: 180
- Sugar: 18g
- Sodium: 75mg
- Fat: 8g
- Saturated Fat: 5g
- Unsaturated Fat: 2g
- Trans Fat: 0g
- Carbohydrates: 25g
- Fiber: 0g
- Protein: 2g
- Cholesterol: 35mg
