Pineapple Upside Sugar Cookies Recipe

If you love the tropical charm of pineapple combined with the timeless delight of sugar cookies, then you are absolutely going to swoon over this Pineapple Upside Sugar Cookies Recipe. Imagine soft, buttery cookies dotted with juicy pineapple and crowned with a sweet maraschino cherry, all with a subtle caramelized brown sugar sprinkle that gives a nod to classic pineapple upside-down cake. This recipe brings together that nostalgic flavor in a fun, handheld treat that’s perfect for sharing or savoring with your favorite cup of tea.

Ingredients You’ll Need

Every ingredient in this Pineapple Upside Sugar Cookies Recipe plays a crucial role, from creating that tender, melt-in-your-mouth texture to providing those bursts of natural sweetness and color. Let’s take a look at what you’ll need to make this delightful tropical twist.

• 1 cup unsalted butter, softened: Provides a rich, creamy base that ensures tender cookies.
• 1 cup granulated sugar: Sweetens and helps achieve that perfect golden-brown finish.
• 1 egg: Binds the dough and adds a touch of moisture for softness.
• 1 teaspoon vanilla extract: Enhances the flavor with warm, comforting notes.
• 2 1/2 cups all-purpose flour: The foundation for structure and chewiness.
• 1/2 teaspoon baking powder: Gives just the right lift and lightness.
• 1/4 teaspoon salt: Balances sweetness and elevates all the flavors.
• 1/2 cup crushed pineapple, drained: Adds juicy tropical bursts and natural sweetness.
• Maraschino cherries, halved: Brings vibrant color and a classic pineapple upside-down charm.
• Brown sugar for sprinkling: Creates a caramel-like finish that perfectly complements the pineapple.

How to Make Pineapple Upside Sugar Cookies Recipe

Step 1: Prepare Your Oven and Baking Sheet

Start by preheating your oven to 350°F (175°C). Line a baking sheet with parchment paper to prevent sticking and ensure even baking, setting the stage for perfectly shaped cookies every time.

Step 2: Cream Butter and Sugar

In a large mixing bowl, cream together the softened unsalted butter and granulated sugar until the mixture becomes light and fluffy. This step is crucial for building that tender crumb and sweet flavor base.

Step 3: Add Egg and Vanilla

Mix in the egg and vanilla extract thoroughly. The egg adds moisture and helps bind the ingredients, while the vanilla enhances the cookie’s rich flavor profile.

Step 4: Combine Dry Ingredients

In a separate bowl, whisk together the all-purpose flour, baking powder, and salt. Gradually add this dry mix to the wet ingredients, stirring until everything is just combined to create a soft but manageable dough.

Step 5: Fold in Crushed Pineapple

Gently fold the drained crushed pineapple into the cookie dough. This juicy addition gives the cookies a delightful burst of tropical sweetness and moisture without overpowering the texture.

Step 6: Shape the Cookies

Scoop tablespoon-sized balls of dough and place them on your prepared baking sheet, making sure to space each cookie apart to allow for spreading during baking.

Step 7: Add Cherry and Brown Sugar Topping

Press a halved maraschino cherry firmly into the center of each cookie ball, then sprinkle a pinch of brown sugar over the top to give that signature caramelized touch reminiscent of pineapple upside-down cake.

Step 8: Bake to Perfection

Bake your cookies in the preheated oven for 10 to 12 minutes, or until the edges are just turning golden. Keep an eye on them to avoid overbaking, as you want a soft center with a gentle crisp around the edges.

Step 9: Cool and Enjoy

Allow the cookies to cool on the baking sheet for a few minutes before transferring them to a wire rack. This lets the bottoms set up nicely and prevents breakage, ensuring every cookie stays intact and delicious.

How to Serve Pineapple Upside Sugar Cookies Recipe

Garnishes

To elevate your Pineapple Upside Sugar Cookies Recipe, try sprinkling a tiny bit of powdered sugar over the cooled cookies for a delicate snowy look. You might also add small fresh mint leaves for a refreshing contrast in both aroma and presentation.

Side Dishes

These cookies pair beautifully with a chilled glass of coconut milk or a bright, citrusy iced tea to complement the tropical flavors. For a more indulgent treat, serve alongside a scoop of vanilla ice cream or a dollop of whipped cream.

Creative Ways to Present

For parties or gift-giving, arrange the cookies in a colorful tin lined with tropical-themed paper. Or stack them with parchment paper between each layer for an Instagram-worthy dessert tower. You could even serve them on a platter alongside other pineapple-inspired treats for a delightful tropical spread.

Make Ahead and Storage

Storing Leftovers

Store your Pineapple Upside Sugar Cookies Recipe leftovers in an airtight container at room temperature. They will stay fresh and soft for up to 4 days, making them perfect for enjoying over several days or sharing with friends.

Freezing

You can freeze the baked cookies by placing them in a single layer on a baking sheet until firm, then transferring them to a zip-top bag or airtight container. Frozen cookies can be kept for up to 3 months and thawed at room temperature whenever a sweet tropical craving hits.

Reheating

If you want that just-baked warmth, pop your cookies in a microwave for about 10 seconds or in a preheated oven at 325°F (160°C) for 5 minutes. This will revive their soft, tender texture and enhance the caramelized brown sugar topping.

FAQs

Can I use fresh pineapple instead of canned crushed pineapple?

Absolutely! Just make sure to finely chop the fresh pineapple and drain it well to avoid extra moisture that might affect the cookie dough consistency.

Why do the cookies need brown sugar sprinkled on top?

The brown sugar provides a small caramelized crunch and deep molasses flavor that beautifully echoes the pineapple upside-down cake tradition, making these cookies extra special.

Are these cookies suitable for freezing before baking?

Yes, you can scoop and freeze the dough balls on a tray. Then, bake them straight from frozen, adding a couple of extra minutes to the baking time for perfect results.

Can I substitute margarine or shortening for butter?

Butter is preferred for the best flavor and texture, but if necessary, you can use margarine. Avoid shortening as it will change the flavor and mouthfeel of the cookies.

How do I prevent the cookies from spreading too much?

Make sure your butter is softened but not melted, and chill the dough briefly if your kitchen is warm. Proper spacing on the baking sheet also helps maintain their shape.

Final Thoughts

If you’re craving something that combines the bright, tropical flavors of pineapple with the comforting sweetness of sugar cookies, this Pineapple Upside Sugar Cookies Recipe is an absolute must-try. It’s a joyful twist that brings sunshine into every bite, whether you’re sharing with loved ones or indulging in a little self-care moment. So gather your ingredients and dive into this delicious adventure — your taste buds will thank you!

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