Christmas Pineapple Upside-Down Sugar Cookies Recipe
Looking for a holiday treat that is equal parts whimsical and irresistible? Invite a burst of festive flavor into your celebrations with Christmas Pineapple Upside-Down Sugar Cookies! This clever twist on a classic dessert delivers buttery sugar cookies kissed with vanilla, crowned with caramelized pineapple and jewel-bright cherries. Each delightful bite combines nostalgia and cheer, turning your holiday cookie tray into a showstopping centerpiece everyone will remember.
Ingredients You’ll Need
These cookies come together with a handful of easy-to-find ingredients, yet every single one plays a starring role. From tangy pineapple to rich buttery dough, each element brings its magic, creating a beautifully balanced cookie that’s part cake, part cookie, all Christmas joy.
- Unsalted butter (softened, 1/2 cup): Creams with sugar for a tender, melt-in-your-mouth cookie base.
- Granulated sugar (3/4 cup): Sweetens the dough and supports the cookie’s soft texture.
- Large egg (1): Binds the dough together for a light, cohesive crumb.
- Vanilla extract (1 teaspoon): Adds warm, aromatic depth that enhances every other flavor.
- All-purpose flour (1 1/2 cups): Provides sturdy, reliable structure that holds the upside-down toppings perfectly.
- Baking powder (1/2 teaspoon): Gives the cookies loft without making them cakey.
- Baking soda (1/4 teaspoon): Works with the acid in sour cream for extra tenderness.
- Salt (1/4 teaspoon): Balances the sweetness and brings out the best in the pineapple.
- Sour cream (1/4 cup): Adds richness and a subtle tang that highlights the fruit.
- Brown sugar (1/4 cup): Caramelizes with butter for a gooey, golden topping.
- Unsalted butter, melted (1/4 cup): Blends with brown sugar for the signature upside-down layer.
- Maraschino cherries (12): Bright red and sweet; the festive crown for each cookie.
- Pineapple tidbits, drained and patted dry (1 cup): Their juicy tang is the heart of this tropical-inspired treat—make sure they’re extra dry for best results!
How to Make Christmas Pineapple Upside-Down Sugar Cookies
Step 1: Prepare Your Muffin Tin
Begin by preheating your oven to 350°F (175°C) and lightly greasing a 12-cup muffin tin. This gives you perfectly shaped cookies that pop out neatly, looking just like miniature upside-down cakes. Using a nonstick spray or a little extra butter is the secret to those golden edges and easy release later on.
Step 2: Create the Caramelized Fruit Layer
In a small bowl, combine the melted butter with the brown sugar, stirring until it forms a smooth caramel mixture. Spoon about one teaspoon of this mixture into the bottom of each muffin cup—it’ll bubble up and turn gorgeously gooey as the cookies bake. Next, press a maraschino cherry in the center of each cup, and tuck a few pineapple tidbits around each cherry. This creates that signature upside-down look and infuses every bite with sweet-tart fruitiness.
Step 3: Mix the Cookie Dough
In a large mixing bowl, cream together the softened unsalted butter and granulated sugar until the mixture is light, fluffy, and pale in color. This will lay the foundation for the tender sugar cookie texture of your Christmas Pineapple Upside-Down Sugar Cookies. Beat in the egg and fragrant vanilla extract until everything is smooth and combined.
Step 4: Combine Dry Ingredients
In a separate bowl, whisk together the all-purpose flour, baking powder, baking soda, and salt. This simple step ensures even distribution of the leavening agents, so each bite rises perfectly and is never dense or heavy.
Step 5: Bring It All Together
Gradually add the dry flour mixture to the butter-sugar mixture, alternating with dollops of sour cream. Stir gently after each addition, just until a soft, cohesive dough forms. The sour cream works its magic here, making these cookies plush and flavorful with a lovely crumb.
Step 6: Assemble the Cookies
Scoop about two tablespoons of cookie dough into each prepared muffin cup, spreading gently to cover the pineapple and cherry. It’s okay if it looks a little rustic—the dough will bake up around the fruit, hugging it in a delicious embrace. Give each cup a gentle tap to settle the dough and ensure an even surface.
Step 7: Bake and Unmold
Slide your muffin tin into the oven and bake for 15 to 18 minutes, or until the tops of the cookies are lightly golden and set. Let the cookies cool for about five minutes (a little patience here makes all the difference!), then carefully invert the pan onto a wire rack or serving tray. You’ll be rewarded with a tray of glossy, golden-topped Christmas Pineapple Upside-Down Sugar Cookies that look as cheerful as Christmas morning.
How to Serve Christmas Pineapple Upside-Down Sugar Cookies
Garnishes
A light dusting of powdered sugar adds a classic snowy touch, making these cookies extra festive. For even more holiday sparkle, try a scattering of edible gold stars or a drizzle of vanilla glaze for a beautiful sheen. The bright red cherries and golden pineapple already do most of the decorating work for you!
Side Dishes
Balance out your dessert spread by serving these cookies alongside a platter of fresh citrus slices or a bowl of creamy vanilla ice cream. If you’re planning a holiday cookie exchange, pair them with chocolate-dipped biscotti or spiced gingerbread men for a fun mix of flavors and textures. A cup of hot cocoa or spiced chai tea is the perfect sip to go with each bite.
Creative Ways to Present
Try packaging the Christmas Pineapple Upside-Down Sugar Cookies in clear cellophane bags tied with crimson ribbon for delightful edible gifts. For a party, arrange them on a tiered cake stand with sprigs of rosemary or holly tucked in between, creating an edible holiday centerpiece. You can also stack them in cookie boxes lined with parchment for gift-giving that looks as good as it tastes!
Make Ahead and Storage
Storing Leftovers
If any cookies survive the holiday rush, store them in an airtight container in the refrigerator for up to three days. The flavors stay vibrant, and a quick warm-up brings them right back to fresh-baked bliss. Keep parchment or wax paper between the layers to prevent sticking.
Freezing
To freeze, arrange cooled cookies in a single layer on a tray and freeze until firm, then transfer to a freezer-safe bag or container. They’ll keep for up to three months. When ready to enjoy, thaw in the refrigerator or at room temperature for maximum freshness and minimal mess.
Reheating
For that just-baked taste, warm individual cookies in the microwave for about 10 to 15 seconds or pop several into a low oven (300°F) for a few minutes. This brings the caramelized pineapple and soft sugar cookie texture right back to life—the ultimate treat on a chilly day!
FAQs
Can I use fresh pineapple instead of canned tidbits?
Absolutely! Just make sure to cut your fresh pineapple into small pieces and pat them very dry before adding to the muffin tin. This prevents excess juice from making the cookies soggy, helping you capture all the bright flavor and cheerful appeal of Christmas Pineapple Upside-Down Sugar Cookies.
What if I don’t have a muffin tin?
You can use ramekins or even a mini cake pan—just be sure to adjust the baking time slightly and keep an eye on the cookies as they bake. The shape will be a little different, but the irresistible flavors will stay true to the original.
How do I prevent the cookies from sticking to the pan?
Be generous with your nonstick spray or butter when prepping your tins, and wait the recommended five minutes before unmolding. Running a thin knife around the edge can also help loosen any stubborn spots, ensuring your Christmas Pineapple Upside-Down Sugar Cookies pop out perfectly.
Can I make the dough ahead of time?
Yes! You can prepare the cookie dough up to 24 hours in advance and refrigerate it tightly covered. When you’re ready to bake, let it soften at room temperature for about 20 minutes, then scoop into your prepared muffin tin as directed.
Are there any nut-free or allergy adaptations for this recipe?
This recipe is naturally nut-free, a huge bonus for holiday gatherings. For dairy-free needs, swap the butter for a plant-based alternative and use a vegan sour cream to keep the cookies soft and delicious. Always double-check your substitutions to ensure they work well with the other ingredients.
Final Thoughts
Nothing says “holiday magic” quite like baking a batch of Christmas Pineapple Upside-Down Sugar Cookies. These cookies are festively bright, impossibly soft, and bursting with unexpected flavor. There’s real joy in every bite, and I can’t wait for you to experience it. Bake a batch and watch them disappear—their playful charm simply can’t be beat!
Print
Christmas Pineapple Upside-Down Sugar Cookies Recipe
- Total Time: 38 minutes
- Yield: 12 cookies 1x
- Diet: Vegetarian
Description
Indulge in the festive spirit with these delightful Christmas Pineapple Upside-Down Sugar Cookies. A unique twist on a classic dessert, these cookies are sure to be a hit at your holiday gatherings.
Ingredients
Dough:
- 1/2 cup unsalted butter (softened)
- 3/4 cup granulated sugar
- 1 large egg
- 1 teaspoon vanilla extract
- 1 1/2 cups all-purpose flour
- 1/2 teaspoon baking powder
- 1/4 teaspoon baking soda
- 1/4 teaspoon salt
- 1/4 cup sour cream
Topping:
- 1/4 cup brown sugar
- 1/4 cup unsalted butter (melted)
- 12 maraschino cherries
- 1 cup pineapple tidbits (drained and patted dry)
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: Mix melted butter and brown sugar, spoon into muffin cups, add cherry and pineapple.
- Make the dough: Cream butter and sugar, add egg and vanilla. In a separate bowl, whisk flour, baking powder, baking soda, and salt. Combine dry ingredients with butter mixture and sour cream.
- Assemble and bake: Scoop dough into muffin cups, bake for 15-18 minutes until golden. Cool slightly, then invert onto a wire rack.
Notes
- Ensure pineapple is well-drained to prevent excess liquid.
- Best enjoyed fresh or store in the refrigerator for up to 3 days.
- Warm cookies before serving for optimal taste.
- Prep Time: 20 minutes
- Cook Time: 18 minutes
- Category: Dessert, Holiday
- Method: Baking
- Cuisine: American
Nutrition
- Serving Size: 1 cookie
- Calories: 210
- Sugar: 21 g
- Sodium: 90 mg
- Fat: 9 g
- Saturated Fat: 5 g
- Unsaturated Fat: 3 g
- Trans Fat: 0 g
- Carbohydrates: 31 g
- Fiber: 1 g
- Protein: 2 g
- Cholesterol: 35 mg
