Pineapple Upside Sugar Cookies Recipe

Imagine the sweet, sunny flavors of pineapple upside-down cake transformed into adorable, nostalgic treats — that’s exactly what you’ll get with these Pineapple Upside Sugar Cookies. Each cookie is like a bite-sized vacation: buttery, golden, and soft, layered with juicy pineapple, a hint of caramelized brown sugar, and topped with a bright maraschino cherry. If you’re looking for something playful, impressive, and incredibly easy to whip up, this delightful dessert is about to become your new go-to favorite. Your friends and family won’t believe just how much charm and tropical joy these humble cookies bring to the table!

Ingredients You’ll Need

this Recipe

Ingredients You’ll Need

The ingredients list is blissfully short and straightforward, but every component genuinely matters in creating the perfect Pineapple Upside Sugar Cookies. From the tropical tang of pineapple to the buttery base and sweet cherry topper, each brings texture, aroma, and color to these cheerful bakes.

• All-purpose flour: The foundation of your cookies, providing just enough structure for a soft yet sturdy bite.
• Baking soda: Helps your cookies rise and stay fluffy instead of dense.
• Salt: Just a pinch brings out all the sweet, distinct flavors and balances the sugar.
• Unsalted butter (softened): Gives your cookies rich flavor and a tender, melt-in-your-mouth texture.
• Granulated sugar: Sweetens the cookies and ensures a classic sugar cookie crumb.
• Large egg: Binds everything together and gives your cookies a little extra lift.
• Vanilla extract: Brings a deep, rounded aroma that complements the pineapple beautifully.
• Pineapple juice: Adds real pineapple zing and moisture to the dough.
• Crushed pineapple (drained well): Packs bursts of juicy flavor and charming specks throughout each cookie.
• Brown sugar: Sprinkled in the base for a gooey, caramelized touch that mimics classic pineapple upside-down cake.
• Maraschino cherries (halved): The cheerful signature “crown” on every cookie.
• Unsweetened shredded coconut (optional): Adds a hint of chew and extra tropical flair — use it if you love coconut!

How to Make Pineapple Upside Sugar Cookies

Step 1: Prep the Oven and Muffin Tin

Start by preheating your oven to 350°F (175°C) for an even, golden bake. Line a standard muffin tin with paper liners or give each cup a light grease to ensure easy cookie removal — this step is key, since the juicy pineapple and sticky brown sugar can make these cookies clingy if left unchecked!

Step 2: Mix the Dry Ingredients

Grab a medium bowl and whisk together the flour, baking soda, and salt. This quick mix ensures your leavening is evenly distributed, guaranteeing every Pineapple Upside Sugar Cookie will bake up light and tender.

Step 3: Cream the Butter and Sugar

In a larger mixing bowl, cream the softened butter with the granulated sugar until it’s pale, fluffy, and almost cloud-like. This step introduces air, making for cookies that are especially soft and luxurious.

Step 4: Add Egg, Vanilla, and Pineapple Juice

Beat in your egg, vanilla extract, and pineapple juice, mixing until everything is fully combined. The pineapple juice infuses your dough with its signature sweet tang, setting these cookies apart from your average sugar cookies.

Step 5: Bring the Dough Together

Gradually add your dry ingredient mixture to the wet ingredients, stirring gently just until no flour remains. Take care not to overmix — you want a tender crumb, not tough cookies. Gently fold in the well-drained crushed pineapple; this is when your dough transforms from classic to downright dreamy.

Step 6: Assemble the Cookies in the Tin

In the bottom of each muffin cup, sprinkle a small pinch of brown sugar. Place half a maraschino cherry, cut-side down, right in the center. This setup gives each Pineapple Upside Sugar Cookie its signature “upside-down cake” appearance and gooey caramelized base.

Step 7: Add Dough and Toppings

Spoon about 1½ tablespoons of cookie dough over each prepared cup, smoothing the tops gently. If you’re a coconut fan, now’s the moment to sprinkle a little unsweetened shredded coconut over each cookie for extra texture and, frankly, a lot of charm.

Step 8: Bake to Golden Perfection

Pop your cookies into the preheated oven and bake for 12 to 15 minutes. You’re looking for golden edges while the centers remain just set — this is the secret to a perfectly chewy, decadent Pineapple Upside Sugar Cookie.

Step 9: Cool and Remove

Let the cookies cool in the muffin tin for about 5 minutes; this helps the base set and makes removal much easier. Carefully lift each cookie out and transfer to a wire rack to cool completely — or sneak one while it’s still just a little warm for maximum swoon!

How to Serve Pineapple Upside Sugar Cookies

Garnishes

These cookies are already gorgeous with their glistening cherry and golden pineapple, but for extra pizzazz, try a light dusting of powdered sugar or even a drizzle of melted white chocolate. A small sprinkle of toasted coconut can also elevate the “tropical vacation” vibes!

Side Dishes

Enjoy Pineapple Upside Sugar Cookies with a scoop of vanilla or coconut ice cream for dessert, or pair them with a frosty tropical drink like pineapple lemonade or an iced coconut latte for an afternoon pick-me-up. They’re perfect for everything from brunch spreads to holiday cookie platters.

Creative Ways to Present

For a fun twist, arrange your cookies on a cake stand, staggered in layers, to echo a vintage pineapple upside-down cake. You can also serve them in colorful cupcake wrappers at a tropical-themed party or package them up in gift boxes tied with raffia for an irresistible homemade gift.

Make Ahead and Storage

Storing Leftovers

Keep Pineapple Upside Sugar Cookies fresh by storing them in an airtight container at room temperature. They’ll maintain their chewy, moist centers for up to three days and are just as lovely on day two as they are straight from the oven.

Freezing

To freeze, arrange cooled cookies in a single layer on a tray until firm, then transfer to a zip-top freezer bag or airtight container. They can be frozen for up to two months. Thaw cookies at room temperature for maximum flavor and texture.

Reheating

Craving that fresh-baked warmth? Just pop a Pineapple Upside Sugar Cookie in the microwave for 8–10 seconds. This brings back the gooey caramel and revives the sunshine flavors, making your treat taste practically oven-fresh!

FAQs

Can I make the dough ahead of time?

Yes! You can mix the dough for Pineapple Upside Sugar Cookies and keep it covered in the fridge for up to 24 hours before baking. Let it come to room temperature before assembling and baking for the best results.

What’s the best way to drain the crushed pineapple?

Press the crushed pineapple gently in a fine-mesh strainer or between layers of paper towels to remove excess moisture. This step is important so your cookies don’t turn out soggy or too dense.

Can I use fresh pineapple instead of canned?

You sure can! Just finely chop fresh pineapple and squeeze out any extra juice before measuring. The flavor will be extra-bright and delicious — just be careful not to let the pieces be too large.

How do I keep the cookies from sticking to the pan?

Line your muffin tin with paper liners or thoroughly grease with non-stick spray. The caramelized brown sugar base can be sticky, so don’t skip this step for smooth cookie removal.

Are Pineapple Upside Sugar Cookies good for gifting?

Absolutely! These cookies travel well and are irresistibly cute in boxes or tins. Wrap them up individually or stack them, and you’ll have the most memorable edible gifts at any get-together.

Final Thoughts

If you’re ready to brighten up your baking routine, Pineapple Upside Sugar Cookies are just the treat for you. The tropical flavors, classic comfort, and playful charm will have everyone reaching for seconds. Give them a whirl, and let a little bite-sized sunshine sweeten your day!

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