Nothing captures the spirit of holiday baking quite like these show-stopping, delightfully nostalgic Christmas Pineapple Upside-Down Sugar Cookies. With their jewel-bright cherry centers, tangy pineapple topping, and buttery sugar cookie base, these little treats are as beautiful as they are delicious. The moment you invert them out of the pan and see those golden bits of fruit peeking through, you’ll understand why they’re the star of every Christmas cookie platter. Gather your loved ones—it’s time to create sweet holiday memories, one scrumptious bite at a time!
Ingredients You’ll Need
Ingredients You’ll Need
The ingredient list is refreshingly straightforward, but each component plays a crucial part in crafting that signature taste, festive color, and irresistible texture. From the juicy pineapple and cherries to the buttery cookie dough, every element helps transform a humble cookie into a centerpiece-worthy holiday dessert.
- Unsalted butter (1/2 cup softened): Gives your cookies a rich, melt-in-your-mouth texture and classic sugar cookie flavor.
- Granulated sugar (1/2 cup): Provides sweetness and helps the cookies spread just enough while baking.
- Light brown sugar (1/4 cup, plus 1/4 cup for topping): Adds deep caramel notes to both the dough and the syrupy pineapple topping.
- Large egg (1): Binds the dough together and ensures a soft, tender crumb.
- Vanilla extract (1 tsp): Enhances all the flavors and brings that classic bakery aroma.
- All-purpose flour (1 1/2 cups): The backbone of your cookies, giving them structure while staying tender.
- Baking soda (1/2 tsp): Provides a gentle lift so the cookies bake up light, not dense.
- Salt (1/4 tsp): Balances sweetness and brightens the cookie’s flavors.
- Crushed pineapple, well-drained (1/2 cup): The tropical, juicy star that makes these cookies sing.
- Maraschino cherries, halved (1/4 cup): Adds a festive pop of color and a sweet finish.
- Unsalted butter, melted (2 tbsp, for topping): Combines with brown sugar for that signature sticky-sweet bottom (which becomes the top!).
How to Make Christmas Pineapple Upside-Down Sugar Cookies
Step 1: Prepare the Muffin Tin
Start by preheating your oven to 350°F (175°C). Give your muffin tin a quick greasing or line it with paper liners to ensure those cookies pop out fuss-free. This step sets the stage for that glorious flip you’ll do at the end.
Step 2: Build the Pineapple-Cherry Base
Mix together 1/4 cup brown sugar and 2 tablespoons of melted butter. Spoon about 1 teaspoon of this mixture into the bottom of each muffin cup. Now, drop in about 1 teaspoon of well-drained crushed pineapple and nestle half a maraschino cherry right in the center. This bright, fruity mixture will become the eye-catching “top” of your Christmas Pineapple Upside-Down Sugar Cookies.
Step 3: Cream the Butter and Sugars
In a large bowl, use an electric mixer to beat the softened butter, granulated sugar, and 1/4 cup brown sugar together until the mixture is light, fluffy, and pale. This step is crucial for creating that pillowy, melt-in-your-mouth sugar cookie base.
Step 4: Add Egg and Vanilla
Beat in your egg and vanilla extract until everything is smooth and creamy. The vanilla adds that unmistakable bakery aroma that makes cookies so irresistible.
Step 5: Combine Dry Ingredients
In a separate bowl, whisk together the flour, baking soda, and salt. Add these dry ingredients gradually to the wet mixture, stirring until a soft dough forms. Be gentle at this stage to keep the cookies tender.
Step 6: Assemble and Bake
Scoop about a heaping tablespoon of dough into each prepared muffin cup—right on top of the pineapple-cherry mixture. Gently press it down so the dough covers the fruit layer completely. Slide the tin into your oven and bake for 12–15 minutes, or until the edges are beautifully golden and just beginning to pull away from the sides.
Step 7: Unmold and Cool
Let the cookies cool in the pan for 5 minutes (this sets the topping and keeps fingers safe!). Carefully invert the muffin tin onto a cooling rack, tapping gently if needed, so you unveil those gorgeous, glistening pineapple-cherry tops. Let the Christmas Pineapple Upside-Down Sugar Cookies cool completely before moving to a serving platter.
How to Serve Christmas Pineapple Upside-Down Sugar Cookies
Garnishes
A simple dusting of powdered sugar brings a touch of snowy magic to each cookie. If you want an extra flourish, add a small mint leaf leaf or a drizzle of white chocolate for a dazzling finish that makes your Christmas Pineapple Upside-Down Sugar Cookies even more eye-catching.
Side Dishes
Pair these cookies with a steaming mug of spiced tea, eggnog, or cinnamon hot chocolate. Their bright, fruity flavor is also the perfect partner for a scoop of vanilla bean ice cream or a dollop of whipped cream, making dessert time feel like a holiday event.
Creative Ways to Present
For a festive touch, arrange the cookies on a vintage holiday platter and nestle sprigs of fresh rosemary or holly between them. Or, tuck each cookie into a cupcake wrapper and present them in a decorative tin as a charming homemade gift. No one can resist a box of Christmas Pineapple Upside-Down Sugar Cookies tied with a festive bow!
Make Ahead and Storage
Storing Leftovers
Place any leftover cookies in a single layer inside an airtight container. They’ll stay soft, moist, and delicious for up to 3 days at room temperature. If stacking, be sure to place parchment between layers to keep the fruit topping looking perfect.
Freezing
You can freeze these cookies after they’ve completely cooled. Arrange them in a single layer in an airtight container, separated by parchment or wax paper. For best flavor and texture, enjoy your thawed Christmas Pineapple Upside-Down Sugar Cookies within one month.
Reheating
If you crave that just-baked taste, pop the cookie in a microwave for 8–10 seconds or in a 300°F oven for 2 minutes. This revives the texture and reawakens that irresistible pineapple aroma, making each bite taste oven-fresh.
FAQs
Can I make these cookies in advance for a cookie swap?
Absolutely! You can bake them a day or two ahead of time and store in an airtight container. They keep their beautiful texture and festive appearance, making Christmas Pineapple Upside-Down Sugar Cookies perfect for gifting or sharing.
What if I can’t find crushed pineapple?
No worries! Simply pulse pineapple chunks or rings in a food processor until finely chopped, then drain thoroughly. Well-drained fruit ensures you’ll have neat, jammy tops and not soggy bottoms on your cookies.
Can I use a different fruit instead of cherries?
Definitely! Candied cranberries, red currants, or even pieces of candied orange can be substituted for the cherries, giving the Christmas Pineapple Upside-Down Sugar Cookies a unique look while preserving that jolly holiday vibe.
How do I prevent the cookies from sticking to the muffin tin?
A generous greasing of your muffin tin with butter or nonstick spray is essential. If you want extra insurance, use parchment paper circles or line each cup with a paper liner for easy removal.
Can I double the recipe?
Yes! This recipe scales beautifully. Just be sure not to overfill your muffin cups and maybe rotate the pans halfway through baking for even browning when making a larger batch of Christmas Pineapple Upside-Down Sugar Cookies.
Final Thoughts
If you’re seeking a holiday treat that dazzles both the eyes and taste buds, don’t wait another minute to bake up a batch of these Christmas Pineapple Upside-Down Sugar Cookies. Their irresistible mix of buttery dough and jewel-bright fruit will have everyone reaching for seconds—so don’t be surprised if they vanish in a flash!
Print
Christmas Pineapple Upside-Down Sugar Cookies Recipe
- Prep Time: 20 minutes
- Cook Time: 15 minutes
- Total Time: 35 minutes
- Yield: 12 cookies
- Category: Dessert
- Method: Baking
- Cuisine: American
- Diet: Vegetarian
Description
Delight your taste buds with these festive Christmas Pineapple Upside-Down Sugar Cookies. A mini upside-down dessert that combines the flavors of pineapple, cherries, and buttery sugar cookie dough, perfect for holiday gatherings or festive treats.
Ingredients
For the Cookie Dough:
- 1/2 cup unsalted butter (softened)
- 1/2 cup granulated sugar
- 1/4 cup light brown sugar
- 1 large egg
- 1 tsp vanilla extract
- 1 1/2 cups all-purpose flour
- 1/2 tsp baking soda
- 1/4 tsp salt
Toppings:
- 1/2 cup crushed pineapple (drained well)
- 1/4 cup maraschino cherries (halved)
- 1/4 cup brown sugar (for topping)
- 2 tbsp unsalted butter (melted, for topping)
Instructions
- Preheat the Oven: Preheat the oven to 350°F (175°C) and lightly grease or line a muffin tin.
- Prepare Toppings: In a small bowl, mix 1/4 cup brown sugar and 2 tablespoons melted butter. Spoon about 1 teaspoon of this mixture into the bottom of each muffin cup. Add crushed pineapple and half a cherry on top of the sugar-butter mixture in each cup.
- Make the Dough: In a large bowl, cream together softened butter, granulated sugar, and brown sugar until light and fluffy. Beat in the egg and vanilla. In a separate bowl, whisk together the flour, baking soda, and salt. Gradually mix the dry ingredients into the wet ingredients until fully combined.
- Assemble Cookies: Scoop dough into each muffin cup, pressing it over the fruit. Bake for 12–15 minutes until lightly golden. Cool in the pan for 5 minutes, then invert onto a rack to release the cookies.
Notes
- Make sure the pineapple is well drained to avoid soggy bottoms.
- Best served the day they’re made but can be stored in an airtight container for up to 3 days.
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