Pineapple Upside Down Sugar Cookies Recipe

If you are anything like me and love a sweet treat with a tropical twist, these Pineapple Upside Down Sugar Cookies are about to become your new obsession. Imagine all the bright, juicy flavor of pineapple combined with the classic buttery sweetness of sugar cookies, turning a nostalgic favorite into bite-sized delights. Each cookie has that golden pineapple ring perched perfectly on top, kissed with a sprinkle of sugar for caramelized sparkle that makes every bite sing. These cookies are simple to make, irresistibly tasty, and guaranteed to brighten up any snack time or dessert plate.

Ingredients You’ll Need

Creating these mouthwatering Pineapple Upside Down Sugar Cookies is straightforward because the ingredients are simple yet so essential. Each one plays a vital role in delivering the perfect balance of texture, flavor, and that classic sugar cookie softness with a bright pineapple pop.

• 1 cup Unsalted Butter, softened: Provides rich creaminess and helps create a tender cookie texture.
• 1 cup Granulated Sugar: Sweetens the cookie and contributes to the light, airy crumb.
• 1 large Egg: Binds everything together and adds moisture for softness.
• 1 teaspoon Vanilla Extract: Adds warmth and depth to the cookie flavor.
• 2 cups All-Purpose Flour: The structure of your cookies comes from this staple ingredient.
• 1 teaspoon Baking Soda: Helps the cookies rise just enough for a soft bite without losing shape.
• 1/2 teaspoon Salt: Balances sweetness and enhances overall flavor.
• 10-12 rings Canned Pineapple, well-drained and patted dry: The star of the show—adds juicy, tangy brightness that pairs perfectly with the sugar cookie base.
• Additional Sugar for Sprinkling: Creates a delightful caramelized crunch on top.

How to Make Pineapple Upside Down Sugar Cookies

Step 1: Prepare Your Oven and Baking Sheets

Start by preheating your oven to 350°F (180°C) and lining your baking trays with parchment paper. This little step makes clean up easier and ensures the cookies won’t stick, letting their golden bottoms shine.

Step 2: Cream the Butter and Sugar

In a large mixing bowl, use an electric mixer to beat the softened butter and granulated sugar together until the mixture is light, creamy, and fluffy. This aeration is key—it gives your cookies that tender, melt-in-your-mouth quality.

Step 3: Add the Egg and Vanilla

Beat in the egg and vanilla extract. This combo adds moisture and a fragrant boost that will fill your kitchen with a warm, inviting aroma.

Step 4: Combine Dry Ingredients

Whisk together the flour, baking soda, and salt in a separate bowl. Then gradually add these dry ingredients to your wet mixture, blending gently just until a soft dough forms. Avoid overmixing to keep the cookies tender instead of tough.

Step 5: Shape the Cookies

Scoop about 2 tablespoons of dough onto your parchment-lined trays, spacing each about 2 inches apart to give them room to spread slightly as they bake. This will make uniform, evenly baked cookies.

Step 6: Add the Pineapple Rings

Gently press a well-drained pineapple ring onto each mound of dough, flattening slightly. If the rings are too large, don’t hesitate to trim or halve them so every cookie gets a perfect-sized piece of pineapple.

Step 7: Sprinkle with Sugar

Dust a little extra granulated sugar over the top of each pineapple ring. This simple touch enhances caramelization as the cookies bake, leaving behind a sparkling, sweet crust that pairs beautifully with the juicy fruit.

Step 8: Bake to Perfection

Bake the cookies for 11 to 13 minutes or until the edges turn a lovely light golden brown and the centers are set. This timing ensures soft, chewy cookie centers that never feel doughy.

Step 9: Cool and Enjoy

Let the cookies cool on the baking tray for a few minutes to firm up before transferring them to a wire rack to cool completely. Watching those pineapple rings hold their shape and glisten when cooled never gets old!

How to Serve Pineapple Upside Down Sugar Cookies

Garnishes

While these cookies are stunning all on their own, you can really dress them up with a light drizzle of honey or a dusting of powdered sugar for added sweetness and visual appeal. A tiny sprig of fresh mint on each cookie also adds a lovely pop of green and a hint of freshness.

Side Dishes

Serve your Pineapple Upside Down Sugar Cookies alongside a cold glass of creamy milk or a tropical fruit smoothie to complement the pineapple flavor. They also make a delightful companion to vanilla ice cream for an easy, warm-and-cool dessert experience.

Creative Ways to Present

Arrange these cookies on a platter surrounded by fresh pineapple chunks and vibrant edible flowers for an eye-catching dessert table centerpiece. Alternatively, stack them with small layers of cream cheese frosting in between for a playful cookie cake twist that’s sure to impress guests.

Make Ahead and Storage

Storing Leftovers

Leftover Pineapple Upside Down Sugar Cookies remain fresh when stored in an airtight container at room temperature for up to 4 days. Keeping them at room temperature helps maintain the perfect soft texture and keeps the pineapple juicy.

Freezing

You can freeze these cookies for longer storage by placing them in a single layer on a baking sheet to freeze until firm, then transferring to a freezer-safe bag or container. This way, you can enjoy your favorite tropical treat anytime by thawing them at room temperature.

Reheating

If you want to warm up a cookie, pop it in the microwave for about 10 seconds or warm in a 300°F oven for 3-4 minutes. This little heat refreshes the softness and brings back that freshly baked aroma and flavor.

FAQs

Can I use fresh pineapple instead of canned rings?

Absolutely! Just make sure to slice the fresh pineapple into rings and pat them dry very well to prevent excess moisture from affecting the cookie dough and texture.

What if I don’t have an electric mixer?

No worries! You can cream the butter and sugar by hand using a sturdy wooden spoon. It will take a little more elbow grease but still yields delicious results.

How do I prevent the pineapple from making the cookies soggy?

Draining the pineapple thoroughly and patting dry is key. Also, pressing the rings gently onto the dough helps the cookie bake evenly without becoming overly moist.

Can I make these cookies gluten-free?

Yes! Swap out the all-purpose flour for a gluten-free baking blend in a 1:1 ratio, and ensure your other ingredients are gluten-free to enjoy these cookies safely.

How long do these cookies stay fresh?

Stored properly in an airtight container, the cookies stay fresh for about 4 days at room temperature, though they tend to be best enjoyed within the first two days for maximum softness.

Final Thoughts

These Pineapple Upside Down Sugar Cookies are such a joyous treat to bake and share. Their bright pineapple sweetness combined with the soft, buttery sugar cookie base are simply irresistible. Whether you’re making them for a tropical-themed party, a special afternoon snack, or just because you want to indulge, I promise they’ll brighten your day. Give this recipe a try and watch these sunny little cookies become an instant favorite in your household!

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