Pineapple Upside Sugar Cookies

What if you could capture the iconic, irresistible magic of a pineapple upside-down cake—the caramelized fruit, the brown sugar glaze, the tender crumb—and transform it into a delightful, hand-held cookie? Enter the genius of Pineapple Upside Sugar Cookies: the perfect fusion of a soft, buttery sugar cookie and the sunny, retro flavor of the classic cake.

These aren’t just cookies with a bit of dried fruit mixed in. This is a clever, two-part creation where each cookie is a miniature individual dessert, featuring a sweet pineapple “flower” nestled in a caramel-like brown sugar glaze on a pillow of tender vanilla dough. They are as beautiful to look at as they are delicious to eat, making them the ultimate showstopper cookie for bake sales, holiday trays, or summer picnics.

If you love the idea of a fun, easy baking project that yields impressive results and transports everyone to a tropical paradise with one bite, this is your recipe. Let’s turn that classic cake into the most charming, crowd-pleasing cookie you’ll make this year.

Why These Cookies Are a Brilliant Twist

This recipe takes the best elements of two classics and combines them seamlessly:

· Individual Portion Perfection: No slicing, no mess. Each cookie is its own complete serving of pineapple upside-down joy.
· The Caramelized Top is the Star: By inverting the baked cookie (just like the cake!), you reveal a stunning, glossy top where the pineapple and maraschino cherry have been baking in a pool of melted butter and brown sugar, creating a heavenly glaze.
· Soft & Sturdy Base: The sugar cookie dough is specifically designed to be sturdy enough to support the juicy topping without becoming soggy, yet tender enough to melt in your mouth.
· Visual Wow Factor: The arranged pineapple and cherry centers create a gorgeous, professional-looking finish with minimal effort. They’re the perfect easy holiday cookie with a tropical twist.

Gathering Your Ingredients

The ingredient list is simple, with a few key players for that signature flavor.

For the Brown Sugar Pineapple Topping:

· 1/2 cup (1 stick / 113g) unsalted butter
· 1 cup (200g) packed light or dark brown sugar (dark will give a deeper molasses flavor)
· 1 can (20 oz) pineapple slices in juice, drained (reserve 2 tablespoons of juice for the dough)
· 10-12 maraschino cherries, halved

For the Soft Sugar Cookie Dough:

· 2 3/4 cups (344g) all-purpose flour
· 1 teaspoon baking soda
· 1/2 teaspoon baking powder
· 1/2 teaspoon salt
· 1 cup (2 sticks / 226g) unsalted butter, softened to room temperature
· 1 1/2 cups (300g) granulated sugar
· 1 large egg, at room temperature
· 2 teaspoons pure vanilla extract
· 2 tablespoons reserved pineapple juice (or milk)

Essential Equipment for Cookie Success

Having the right tools makes this process smooth and enjoyable.

Muffin/Cupcake Pan: A standard 12-cup pan is essential for creating the “well” for the topping and giving the cookies their unique shape.

Stand Mixer or Hand Mixer: For creaming the butter and sugar to the perfect fluffy consistency.

Saucepan: For melting the butter and brown sugar to create the caramel-like topping base.

Cookie Scoop (Medium, ~1.5 Tbsp): For placing uniform amounts of dough into each muffin cup.

Small Juice Glass or Measuring Cup: For pressing the dough into an even layer in the pan.

Cooling Racks: Vital for the flipping and cooling process.

Small Round Cutter or Shot Glass (Optional): For cutting neat circles from the pineapple slices to fit perfectly on the cookies.

Step-by-Step Instructions: Creating Mini Masterpieces

Follow these steps for perfectly portioned, stunning cookies.

Part 1: Prepare the Pineapple Topping & Pan

Step 1: Preheat your oven to 350°F (175°C).
Step 2:In a small saucepan over medium heat, melt the 1/2 cup of butter. Stir in the packed brown sugar until the mixture is smooth and begins to bubble slightly. Remove from heat.
Step 3:Spoon 1 heaping tablespoon of this brown sugar mixture into the bottom of each cup in your muffin pan.
Step 4:Drain the pineapple slices, RESERVING 2 tablespoons of the juice. Using a small round cutter (about 1.5-2 inches in diameter) or a knife, cut small circles from each pineapple slice. You’ll need one circle per cookie. Place one pineapple circle over the brown sugar mixture in each muffin cup. Press one maraschino cherry half, cut-side up, into the center of each pineapple ring. Set the pan aside.

Part 2: Make the Sugar Cookie Dough

Step 5: In a medium bowl, whisk together the flour, baking soda, baking powder, and salt.
Step 6:In your mixer bowl, cream the softened butter and granulated sugar together on medium-high speed for 2-3 minutes, until light and fluffy.
Step 7:Beat in the egg, vanilla extract, and the 2 tablespoons of reserved pineapple juice until combined.
Step 8:With the mixer on low, gradually add the dry ingredients until just incorporated. The dough will be soft but not sticky.

Part 3: Assemble & Bake

Step 9: Using your cookie scoop, place a ball of dough directly on top of the pineapple and cherry in each muffin cup. Using the bottom of a small juice glass (you can grease it lightly), press the dough down gently and evenly to flatten and seal the edges against the pan.
Step 10:Bake for 15-18 minutes, or until the cookie tops are lightly golden and set.
Step 11:CRITICAL COOLING STEP: Remove the pan from the oven and let it cool on a wire rack for only 5 minutes. Any longer and the caramel will harden and stick.

Part 4: The “Upside-Down” Magic

Step 12: After 5 minutes, place a large baking sheet or cutting board over the top of the muffin pan. Wearing oven mitts, firmly and confidently flip the entire pan and tray over in one smooth motion. Gently lift the muffin pan away. The cookies should release easily, revealing their beautiful glazed tops.
Step 13:If any topping sticks to the pan, simply scrape it out and spoon it back onto the cookies. Let the cookies cool completely on the tray.

Pro Tips for Flawless Cookies

· Don’t Skip the Pineapple Juice: The reserved juice in the dough adds a subtle tropical flavor and tenderness you can’t get with milk alone.
· The Perfect Press: When pressing the dough, ensure you push it all the way to the edges to encase the pineapple. This prevents leakage and ensures a clean flip.
· Timing is Everything for the Flip: 5 minutes is the sweet spot. Too hot, and they fall apart; too cool, and the caramel sticks.
· Use a Non-Stick Pan or Grease Lightly: Even with the butter-sugar layer, a quick spritz of non-stick spray in the cups before adding the topping guarantees a clean release.
· For a Cleaner Cut: If you want perfectly round pineapple circles, a small, clean can (like a tomato paste can) works as a great cutter.

Frequently Asked Questions (FAQs)

Can I use fresh pineapple?
It’s not recommended.Canned pineapple is consistently sweet, tender, and moist. Fresh pineapple contains an enzyme (bromelain) that can break down proteins and affect the texture of the cookie dough, and it may not soften and caramelize in the same way.

Can I make these in advance?
Yes!The cookie dough can be made, covered, and refrigerated for up to 2 days before assembling and baking. You can also store the fully baked and cooled cookies in an airtight container at room temperature for 2-3 days.

My topping stuck to the pan! What do I do?
Don’t panic.Simply use a small silicone spatula or knife to gently scrape any stuck caramel and fruit from the pan. While it’s still warm, place it back onto the cookie. It will reset as it cools.

Can I freeze these cookies?
They are best enjoyed fresh,but you can freeze the baked and cooled cookies in a single layer, then transfer to a freezer bag for up to a month. Thaw at room temperature.

What can I use instead of maraschino cherries?
For a more natural option,you can use a fresh or frozen pitted sweet cherry. Alternatively, a single fresh raspberry or a pecan half in the center makes a lovely variation.

Delicious Variations & Serving Ideas

Flavor Twists:

· Coconut Pineapple: Add 1/2 cup of toasted sweetened coconut flakes to the cookie dough. Sprinkle a little more on top after flipping.
· Bourbon Caramel: Add 1 tablespoon of bourbon or dark rum to the brown sugar and butter mixture in the saucepan.
· Ginger-Spiced: Add 1 teaspoon of ground ginger to the dry ingredients for a warm, spicy note.

Serving & Presentation:

· Dessert Platter: Serve them on a platter as individual mini-cakes—no plates or forks needed!
· À La Mode: Serve a slightly warm cookie with a small scoop of vanilla bean or coconut ice cream for an over-the-top dessert.
· Brunch Worthy: These cookies are sweet enough to stand in for coffee cake or muffins at a special brunch gathering.

The Final Bite

Pineapple Upside Sugar Cookies are more than a recipe; they’re a delightful bit of baking theater. They capture the joy of a reveal—the moment you flip the pan and see those glistening, jewel-like tops. They bring the comforting, communal feel of a shared cake into a personalized, grab-and-go treat.

This recipe proves that with a little creativity, you can reinvent a classic in a fun, accessible, and utterly delicious new form. So, break out your muffin pan and get ready to bring a taste of tropical sunshine to your kitchen. One bite of these soft, caramel-glazed, fruity cookies, and you’ll be transported. Happy baking

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