If you’re searching for a delightful twist to your holiday baking, this Christmas Pineapple Upside-Down Sugar Cookies Recipe is the answer. Combining the rich buttery softness of sugar cookies with a tropical touch from pineapple and a festive pop of maraschino cherries, these cookies capture the warmth and joy of Christmas in every bite. They are as charming to look at as they are delicious, making them perfect for sharing with friends and family during the holidays. Trust me, once you try these, they will become a treasured part of your seasonal celebrations.
Ingredients You’ll Need
This recipe keeps things wonderfully simple, using pantry staples that come together to create a cookie that’s flavorful, tender, and visually festive. Each ingredient plays a role in balancing sweetness, texture, and holiday flair.
- 1/2 cup unsalted butter, softened: Gives the cookies a rich, creamy base that keeps them soft and tender.
- 3/4 cup granulated sugar: Sweetens the dough while helping create a light texture.
- 1 large egg: Binds all the ingredients together and adds moisture.
- 1 teaspoon vanilla extract: Adds warmth and depth to the cookie flavor.
- 1 1/2 cups all-purpose flour: Provides structure for these soft yet sturdy cookies.
- 1/2 teaspoon baking powder: Gives a slight lift to the dough, ensuring the cookies puff just right.
- 1/4 teaspoon salt: Enhances all the sweet flavors and balances the taste.
- 6 maraschino cherries, halved: Adds a festive, bright-red accent with a slightly tangy sweetness.
- 1/4 cup crushed pineapple, drained well: Brings juicy, tropical flavor and moisture without making the dough soggy.
- 2 tablespoons brown sugar: Infuses a subtle caramel note that complements the pineapple beautifully.
How to Make Christmas Pineapple Upside-Down Sugar Cookies Recipe
Step 1: Preheat and Prepare
Start by heating your oven to 350°F (175°C) and line a baking sheet with parchment paper. This simple prep ensures your cookies bake evenly and come off the pan effortlessly, preserving their charming shape and colorful toppings.
Step 2: Cream Butter and Sugar
In a mixing bowl, cream together the softened butter and granulated sugar until the mixture looks light and fluffy. This aeration is key to achieving that tender crumb and delightful melt-in-your-mouth texture in the finished cookie.
Step 3: Mix in Egg and Vanilla
Add the large egg and vanilla extract to the creamed butter and sugar, mixing thoroughly. These add moisture and enhance the cookie’s sweet, warm flavor, making every bite a cozy treat.
Step 4: Combine Dry Ingredients
In a separate bowl, whisk the all-purpose flour, baking powder, and salt together. This step ensures your leavening is evenly distributed, so each cookie rises just right while preventing any salty spots.
Step 5: Form the Dough
Gradually incorporate the dry ingredients into the wet mixture until a soft dough forms. Be careful not to overmix—just combine until you have a smooth dough that’s easy to shape.
Step 6: Prepare Pineapple Mixture
Mix the drained crushed pineapple with the brown sugar in a small bowl. This mixture adds a sweet, tangy burst of flavor to the center of each cookie, bringing that classic upside-down cake vibe in a lovely cookie form.
Step 7: Shape and Top Cookies
Scoop about one tablespoon of dough and flatten it into a small circle in your hand or on a work surface. Pinch a bit of the pineapple mixture into the center, then place half a maraschino cherry on top. This is where the magic happens—the sugary pineapple and bright cherry become the star of the cookie’s presentation.
Step 8: Arrange and Bake
Place the cookie rounds onto your prepared baking sheet, leaving about two inches between each so they have room to spread. Bake them for 10 to 12 minutes until the edges turn a lovely golden brown. The aroma at this stage is amazing, hinting at both buttery sweetness and tropical notes.
Step 9: Cool and Enjoy
Allow the cookies to cool for 5 minutes on the baking sheet before transferring them to a wire rack to cool completely. Cooling helps the cookies set so the topping stays beautifully intact, ready to dazzle your holiday guests.
How to Serve Christmas Pineapple Upside-Down Sugar Cookies Recipe
Garnishes
Sprinkle a little powdered sugar over the cookies just before serving for a snowy effect that looks absolutely festive. You can also drizzle a thin glaze made from powdered sugar and pineapple juice for extra shine and sweetness.
Side Dishes
Pair these cookies with a cup of hot spiced tea, mulled wine, or even a glass of cold milk for a classic treat. Their tropical notes balance beautifully with warm, cozy beverages, making each bite even more delightful during chilly holiday evenings.
Creative Ways to Present
Arrange your Christmas Pineapple Upside-Down Sugar Cookies Recipe on a bright holiday platter surrounded by fresh rosemary sprigs and cranberries for an elegant touch. Or stack them in clear jars tied with ribbon, making a perfect edible gift that looks as good as it tastes.
Make Ahead and Storage
Storing Leftovers
Keep leftover cookies in an airtight container at room temperature. They maintain their freshness for about 3 to 4 days, making them perfect to bake ahead and enjoy throughout your holiday festivities without stress.
Freezing
You can freeze these cookies for up to 2 months. Place them in a single layer on a baking sheet first, freeze until solid, then transfer to a freezer-safe container or bag. This way, you can bake a batch ahead of time and enjoy them whenever you want a festive treat.
Reheating
To bring back that freshly baked feeling, warm your cookies in a low oven at 300°F (150°C) for 5 minutes or pop them in the microwave for about 10 seconds. They’ll regain that soft, buttery texture and the pineapple topping will taste just as fresh as when first baked.
FAQs
Can I substitute fresh pineapple for the canned crushed version?
Fresh pineapple can work, but make sure to finely chop it and drain it really well to avoid adding too much moisture, which can make the cookie dough soggy.
What if I don’t have maraschino cherries? What’s a good substitute?
You can use glacé cherries or even fresh cherries if they’re in season. Just cut them into halves or quarters to maintain that classic look and sweetness.
Can I make these cookies gluten-free?
Yes! Swap the all-purpose flour for a gluten-free baking flour blend that measures 1:1. Just be sure your baking powder is gluten-free too, and watch the dough’s texture—it might need a touch less or more flour depending on the blend.
How do I keep the pineapple topping from making the cookies too wet?
Draining the crushed pineapple very well and mixing it with brown sugar helps reduce moisture. Also, only add a small pinch of the pineapple mixture in the center of each cookie rather than a large dollop.
Will these cookies keep their pineapple flavor if made a day in advance?
Absolutely! In fact, letting them rest for a day allows the flavors to meld even more, making the pineapple and cherry notes stand out beautifully when you finally enjoy them.
Final Thoughts
Baking these Christmas Pineapple Upside-Down Sugar Cookies Recipe is a joyful way to add a cheerful, tropical twist to your holiday cookie lineup. They’re easy to make, fun to decorate, and truly unforgettable to eat. Next time you’re looking to impress your guests with something both classic and surprising, give this recipe a whirl—you’ll be making warm holiday memories for years to come.
Print
Christmas Pineapple Upside-Down Sugar Cookies Recipe
- Total Time: 27 minutes
- Yield: 18 cookies 1x
Description
These festive Christmas Pineapple Upside-Down Sugar Cookies combine the classic flavors of pineapple and maraschino cherries with a soft, buttery sugar cookie base. Topped with a sweet pineapple and brown sugar mixture and a cherry half, these cookies offer a delightful twist perfect for holiday celebrations.
Ingredients
Cookie 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 salt
Topping
- 6 maraschino cherries, halved
- 1/4 cup crushed pineapple, drained well
- 2 tablespoons brown sugar
Instructions
- Preheat Oven: Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper to prevent sticking and ensure even baking.
- Cream Butter and Sugar: In a mixing bowl, cream together the softened butter and granulated sugar until the mixture becomes light and fluffy, indicating that air has been incorporated for tender cookies. Then, add the egg and vanilla extract, mixing well to combine.
- Combine Dry Ingredients: In a separate bowl, whisk together the all-purpose flour, baking powder, and salt to evenly distribute the leavening and seasonings.
- Form Dough: Gradually add the dry ingredients to the wet mixture, mixing until a soft dough forms. Be careful not to overmix to maintain tender cookies.
- Prepare Pineapple Topping: In a small bowl, combine the well-drained crushed pineapple with the brown sugar, stirring to create a sweet topping mixture.
- Shape Cookies: Scoop about 1 tablespoon of dough and flatten it gently into a circle. Place a pinch of the pineapple mixture in the center and top with half of a maraschino cherry.
- Arrange and Bake: Place the prepared cookies on the lined baking sheet, spacing them about 2 inches apart to allow for spreading. Bake in the preheated oven for 10-12 minutes, or until the edges turn golden brown.
- Cool: Allow the cookies to cool on the baking sheet for 5 minutes before transferring them to a wire rack to cool completely, ensuring they firm up and develop the perfect texture.
Notes
- Ensure the crushed pineapple is well drained to prevent the dough from becoming too wet.
- For uniform cookies, use a cookie scoop to portion the dough.
- Store cookies in an airtight container at room temperature for up to 5 days.
- These cookies can be made a day ahead; just keep them stored properly to maintain freshness.
- Optional: Sprinkle a little extra brown sugar on top before baking for added caramelization.
- Prep Time: 15 minutes
- Cook Time: 12 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
