Christmas Pineapple Upside-Down Sugar Cookies Recipe
If you’re searching for a show-stopping holiday treat, look no further than these Christmas Pineapple Upside-Down Sugar Cookies. Imagine the classic pineapple upside-down cake, but in a festive, hand-held cookie form—soft, buttery sugar cookie bases, topped with caramelized pineapple, glistening cherries, and a sprinkle of holiday cheer. Each bite is a perfect fusion of tropical sweetness and cozy nostalgia, making these cookies the star of any Christmas cookie tray. Whether you’re baking for a party or wrapping up edible gifts, these cookies always steal the spotlight and bring a big smile to everyone’s face!
Ingredients You’ll Need
The magic behind Christmas Pineapple Upside-Down Sugar Cookies comes from a handful of simple, everyday ingredients—each with a special role in building flavor, texture, and that unmistakable festive flair. Let’s take a closer look at what you’ll need and why it matters!
- Unsalted butter (softened): The creamy backbone of the cookie dough, lending richness and tenderness to every bite.
- Granulated sugar: For sweetness and a light, crisp crumb that defines a classic sugar cookie.
- Large egg: Acts as the binder, helping the dough come together and bake up soft and chewy.
- Vanilla extract: Adds a warm, aromatic note that makes these cookies taste truly homemade.
- All-purpose flour: The structure-builder, creating just the right amount of softness and lift.
- Baking powder: Gives the cookies a gentle rise and prevents them from becoming too dense.
- Salt: Balances the sweetness and sharpens the flavors throughout.
- Light brown sugar: Melts with butter to create that signature caramelized topping on each cookie.
- Unsalted butter (melted): Blends with brown sugar for a gooey, golden base under the fruit.
- Canned pineapple rings (cut into small pieces): The tropical crown of each cookie—juicy, tangy, and bright.
- Maraschino cherries (halved): The iconic ruby center that pops with color and sweetness.
- Red and green sprinkles (optional): A festive finishing touch that makes every cookie sparkle for the holidays!
How to Make Christmas Pineapple Upside-Down Sugar Cookies
Step 1: Prep the Pan and Caramel Layer
Begin by preheating your oven to 350°F and generously greasing a standard muffin tin. In a small bowl, combine the light brown sugar and a tablespoon of melted butter, stirring until you have a sandy, fragrant mixture. Spoon about a teaspoon of this caramel mixture into the bottom of each muffin cup, setting the stage for all that juicy fruit flavor. This easy trick ensures each cookie has its own glossy, caramelized crown.
Step 2: Add the Pineapple and Cherries
Place 3 to 4 small pieces of pineapple in the bottom of each muffin cup, nestling them into the brown sugar mixture. Now, tuck half a maraschino cherry—cut side up—right in the center. This not only adds a burst of color but ensures every Christmas Pineapple Upside-Down Sugar Cookie has that signature, sweet surprise at the heart.
Step 3: Make the Sugar Cookie Dough
In a large mixing bowl, cream together the softened butter and granulated sugar until the mixture is light, fluffy, and pale—this step is key for that melt-in-your-mouth texture. Beat in the egg and vanilla extract, making sure everything is well blended. In a separate bowl, whisk together the flour, baking powder, and salt. Gradually add the dry ingredients to the wet, mixing gently until a soft, cohesive dough forms.
Step 4: Assemble the Cookies
Scoop about 1 1/2 tablespoons of dough into each muffin cup, then gently press and spread the dough so it completely covers the fruit layer. Don’t worry if it doesn’t look perfect—these cookies always bake up beautifully! The dough will seal in the fruit, creating that classic upside-down effect once baked and inverted.
Step 5: Bake to Perfection
Slide the muffin tin into your preheated oven and bake for 15 to 18 minutes, or until the cookie tops turn lightly golden and the edges look set. The aroma will fill your kitchen with pure holiday magic! Let the cookies cool in the pan for about 5 minutes—this helps the topping set just enough for a clean release.
Step 6: Unmold and Garnish
Carefully invert the muffin tin onto a baking sheet so the cookies pop out upside-down and reveal their caramelized, jewel-toned tops. If any fruit sticks, just nudge it back in place. Finish with a sprinkle of red and green sprinkles for an extra burst of Christmas cheer. Serve the cookies warm for gooey goodness or let them cool to room temperature for easy sharing.
How to Serve Christmas Pineapple Upside-Down Sugar Cookies
Garnishes
For a touch of holiday sparkle, top your Christmas Pineapple Upside-Down Sugar Cookies with festive red and green sprinkles right after unmolding. If you want to get extra fancy, a light dusting of powdered sugar or a drizzle of white chocolate can add a snowy effect that’s almost too pretty to eat!
Side Dishes
These cookies shine on their own, but if you’re serving them at a party, pair with a bowl of vanilla bean ice cream or a platter of fresh berries for a delightful contrast. A mug of hot cocoa, spiced tea, or mulled wine makes the perfect cozy companion to their sweet, tangy flavors.
Creative Ways to Present
Turn your Christmas Pineapple Upside-Down Sugar Cookies into edible gifts by packing them in festive tins or clear treat bags tied with ribbon. For a dramatic dessert platter, arrange the cookies in a wreath shape and add sprigs of rosemary or mint for a “holiday greenery” effect that delights the eyes as much as the taste buds.
Make Ahead and Storage
Storing Leftovers
If you find yourself with a few cookies left (which is rare!), store them in an airtight container at room temperature for up to two days. The fruit topping stays moist, and the cookies keep their soft, tender texture for the perfect make-ahead treat.
Freezing
These cookies freeze surprisingly well! Once fully cooled, layer them between sheets of parchment in an airtight container and freeze for up to one month. Thaw at room temperature before serving to bring back their fresh-baked flavor and texture.
Reheating
If you love your Christmas Pineapple Upside-Down Sugar Cookies warm and gooey, just pop one in the microwave for 10–15 seconds. This brings the caramel and fruit back to life, making each bite taste like it’s straight from the oven.
FAQs
Can I use fresh pineapple instead of canned?
Absolutely! Fresh pineapple adds a bold, juicy flavor. Just be sure to cut it into small pieces and pat them dry with paper towels to avoid excess moisture in the muffin tin.
How do I keep the cookies from sticking to the pan?
Generously greasing the muffin tin is key, and you can also use parchment strips in each cup for easy lifting. Letting the cookies cool for a few minutes before inverting also helps prevent sticking.
Can I make these cookies gluten free?
Yes! Swap the all-purpose flour for your favorite gluten-free flour blend (look for one formulated for baking), and check all other ingredients for gluten if you’re sensitive. The results are just as delicious and festive.
What other toppings can I use?
If you want to experiment, try adding a pinch of cinnamon or nutmeg to the brown sugar mixture, or use different fruits like mandarin oranges or blueberries for a unique twist on your Christmas Pineapple Upside-Down Sugar Cookies.
Do I need to serve them warm?
Nope! These cookies taste fantastic both warm and at room temperature. Serving them warm gives you a gooier fruit topping, but they’re just as delightful cooled, which makes them perfect for gifting or parties.
Final Thoughts
Whether you’re a seasoned holiday baker or just looking for something new and fun, these Christmas Pineapple Upside-Down Sugar Cookies are guaranteed to bring joy to your kitchen and smiles to everyone who tries them. Give them a whirl this season—you just might discover your new favorite festive cookie!
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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 combine the classic holiday flavors of pineapple and cherry with a soft, buttery sugar cookie base. Perfectly moist and festive, they make a delightful treat for holiday gatherings or cozy winter afternoons. The inverted presentation reveals a caramelized fruit topping, enhanced with optional red and green sprinkles for a cheerful holiday look.
Ingredients
Cookie Dough
- 1/2 cup unsalted butter (softened)
- 1 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 salt
Topping
- 1/4 cup light brown sugar
- 1 tablespoon unsalted butter (melted)
- 6 canned pineapple rings (cut into small pieces)
- 6 maraschino cherries (halved)
- Red and green sprinkles (optional, for garnish)
Instructions
- Prepare the muffin tin and topping: Preheat the oven to 350°F (175°C) and grease a standard muffin tin thoroughly. In a small bowl, mix the light brown sugar with the melted butter until well combined. Spoon about 1 teaspoon of this mixture into the bottom of each muffin cup. Top each portion with 3 to 4 small pieces of pineapple and half a maraschino cherry placed cut-side up in the center.
- Cream the butter and sugar: In a large mixing bowl, beat the softened unsalted butter together with the granulated sugar until the mixture becomes light and fluffy. This aeration helps create a tender cookie texture.
- Add egg and vanilla: Beat in the egg followed by the vanilla extract until fully incorporated, ensuring a smooth batter.
- Combine dry ingredients: In a separate bowl, whisk together the all-purpose flour, baking powder, and salt to evenly distribute the leavening agent and seasoning through the flour.
- Mix dry ingredients into wet: Gradually add the dry mixture to the wet ingredients, mixing gently but thoroughly until just combined into a soft cookie dough.
- Fill muffin cups with dough: Using a spoon or cookie scoop, place about 1 1/2 tablespoons of dough into each muffin cup, gently pressing it to cover the pineapple and cherry layer evenly.
- Bake: Place the muffin tin into the preheated oven and bake for 15 to 18 minutes, or until cookie tops are lightly golden and a toothpick inserted into the cookie base comes out clean.
- Cool and invert: Allow the cookies to cool in the tin for about 5 minutes. Carefully invert the muffin tin onto a baking sheet or wire rack to release the cookies, revealing the caramelized pineapple and cherry topping.
- Garnish and serve: Optionally sprinkle red and green festive sprinkles on top while the cookies are still warm. Serve the cookies warm or at room temperature for the best flavor and texture.
Notes
- For even easier removal, line the muffin cups with parchment strips before adding the topping and dough.
- These cookies are best served on the same day for optimal freshness but can be stored in an airtight container at room temperature for up to 2 days.
- To add extra holiday flavor, consider mixing a pinch of cinnamon or nutmeg into the dough.
- Prep Time: 20 minutes
- Cook Time: 18 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
Nutrition
- Serving Size: 1 cookie
- Calories: 160
- Sugar: 15 g
- Sodium: 55 mg
- Fat: 7 g
- Saturated Fat: 4 g
- Unsaturated Fat: 3 g
- Trans Fat: 0 g
- Carbohydrates: 23 g
- Fiber: 0 g
- Protein: 1 g
- Cholesterol: 25 mg
