Pineapple Upside Down Sugar Cookies Recipe

If you’re looking to impress friends or simply treat yourself to something unique and nostalgic, these Pineapple Upside Down Sugar Cookies are a game-changer for your dessert repertoire. Imagine the charm of classic pineapple upside down cake, but in the sweet, hand-held form of a pillowy, golden cookie. With a caramelized brown sugar base, juicy pineapple, maraschino cherries, and soft, buttery cookie dough, every bite delivers a burst of tropical flavor and homemade comfort. The best part? They’re just as gorgeous as they are delicious—perfect for parties, gatherings, or any moment that calls for a little sunshine on your plate.

Ingredients You’ll Need

You won’t need anything fancy to make these stunning Pineapple Upside Down Sugar Cookies—just simple pantry staples plus a few colorful, fruity toppings. Each ingredient brings its own flair, working together to create that classic pineapple upside down magic but with the irresistible texture of a sugar cookie.

• Butter (1 cup, room temperature): Gives the cookies their rich, tender crumb and creamy flavor. Make sure it’s nice and soft for easy mixing.
• Granulated sugar (1 1/2 cups): Sweetens the dough and helps create those perfectly crisp edges.
• Eggs (2): Acts as the binder to hold everything together and gives the cookies their signature soft texture.
• Vanilla extract (2 tsp.): Adds warmth and depth—don’t skip this for that cozy sugar cookie aroma.
• Sour cream (1/2 cup): The secret ingredient for softness; it keeps the cookies moist and boosts flavor.
• All-purpose flour (3 cups): The backbone of your dough, giving structure without heaviness.
• Baking powder (1 tsp.): Lifts the cookies and keeps them fluffy—not dense.
• Cornstarch (1 tsp.): Helps produce ultra-soft cookies with a delicate bite.
• Salt (1/2 tsp.): Just a pinch brings out the flavors and balances the sweetness.
• Canned pineapple slices (13): These juicy rings caramelize beautifully and form the show-stopping base.
• Maraschino cherries (13): For that classic, pop-of-red center—charming, festive, and sweet.
• Butter, melted (1/2 cup): Pairs with brown sugar to form that ooey-gooey, caramelized layer.
• Light brown sugar, packed (1 cup): Creates the gooey, sticky topping that seeps into each bite for pure decadence.

How to Make Pineapple Upside Down Sugar Cookies

Step 1: Get Your Pan Ready

Start by preheating your oven to 350 degrees so everything bakes up evenly. Grease a mini round cake pan (or muffin tin if you don’t have one), and set it aside—you’ll want to make sure each cookie releases easily, keeps its shape, and beautifully shows off those pineapple and cherry layers.

Step 2: Make the Sugar Cookie Dough

In a large mixing bowl, combine the room temperature butter and granulated sugar. Beat them together until the mixture is super light and fluffy—this is what makes the cookies over-the-top tender! Add in the eggs, vanilla extract, and creamy sour cream. Continue mixing until everything is smooth and well incorporated. Next, toss in the flour, baking powder, cornstarch, and salt. Give it another mix, just until the dough comes together (you want to avoid overmixing for the softest results!).

Step 3: Prepare the Gooey Caramel Layer

In a separate bowl, stir together the melted butter and packed brown sugar. This gooey golden mixture will bubble and form an incredible caramel layer under the pineapple as the cookies bake. Drop about a tablespoon of it into the bottom of each pan cavity, making sure to spread it out evenly.

Step 4: Assemble Your Pineapple Upside Down Sugar Cookies

Gently lay a pineapple ring right on top of the brown sugar mixture in each cavity, pressing them down so they nestle in. Pop a single maraschino cherry into the center of each pineapple ring—this tiny touch is both adorable and adds a delightful sweet-tart kick.

Step 5: Add and Flatten the Cookie Dough

Using a 3-tablespoon cookie scoop, drop a mound of your sugar cookie dough over each fruit-topped cavity. Use an offset spatula or the back of a spoon to carefully flatten the dough so it covers the fruit completely. This layer bakes up to a pillow-soft finish that cradles the caramel and fruit underneath.

Step 6: Bake to Golden Goodness

Slide the pan into your awaiting oven and bake for 25 minutes, or until the edges of the cookies are delicately golden and you can see caramel bubbling up the sides. The aroma is heavenly—warm brown sugar and pineapple will fill your kitchen with joy!

Step 7: Cool and Flip

Let your cookies cool in the pan for about 10 minutes. This ensures the caramel sets a bit without getting too sticky to handle. Carefully invert the cookies onto a wax paper-lined surface—this wax paper step is important as the caramel can run. If any pineapple slices stick to the pan, simply reposition them atop the cookies (no one will ever know). Let the cookies cool completely before serving so each layer stays intact and picture-perfect.

How to Serve Pineapple Upside Down Sugar Cookies

Garnishes

Sprinkle your Pineapple Upside Down Sugar Cookies with a little extra powdered sugar right before serving for a whimsical snow-like finish, or add a dollop of whipped cream for a truly festive touch. If you want to go all out, finish with a small mint leaf for a pop of color and freshness.

Side Dishes

These cookies shine on their own but pair beautifully with light accompaniments. Serve alongside a scoop of vanilla bean ice cream or a citrusy sorbet to really play up those tropical flavors. A side of fresh-cut fruit or a simple fruit salad is another light and lovely match, highlighting the bright pineapple element in every bite.

Creative Ways to Present

Arrange the Pineapple Upside Down Sugar Cookies on a pretty cake stand or tiered platter for a brunch or baby shower. For a fun twist, serve them warm with tiny scoops of ice cream or drizzle each cookie with a quick pineapple glaze. You can even wrap them individually in cellophane with a colorful ribbon as cheerful party favors that guests will rave about.

Make Ahead and Storage

Storing Leftovers

To keep your Pineapple Upside Down Sugar Cookies fresh, store them in an airtight container at room temperature. They’ll stay soft and delicious for up to 3 days—just make sure to use wax or parchment paper between layers to prevent sticking. The brown sugar caramel can make things a little messy, but that’s part of the fun!

Freezing

You can absolutely freeze these cookies! Let them cool completely, then individually wrap each one in plastic wrap and place them in a freezer-safe bag or container. They will keep fresh for up to a month—just thaw them at room temperature when a craving hits or when you need a show-stopping dessert in a pinch.

Reheating

If you love your Pineapple Upside Down Sugar Cookies warm and gooey, simply pop them in the microwave for about 10-15 seconds. The caramel will soften, the pineapple’s juices will reawaken, and the cookie will taste freshly baked. Be careful not to overheat, or the caramel may become too runny.

FAQs

Can I use fresh pineapple instead of canned?

Yes! Just slice fresh pineapple into rings similar in size to canned, pat dry to remove excess juice, and proceed as directed. Keep in mind fresh pineapple may have a slightly different texture and flavor, but it will be absolutely delicious.

What if I don’t have a mini round cake pan?

No worries! A standard muffin tin works beautifully for Pineapple Upside Down Sugar Cookies—just trim the pineapple slices to fit. The cookies may be a tad smaller, but they’ll still look adorable and taste amazing.

Can I make these cookies gluten-free?

Absolutely! Swap out the all-purpose flour for your favorite gluten-free baking blend, making sure it includes xanthan gum for texture. Everything else in the recipe stays the same, so you don’t miss any flavor or joy!

Do these cookies need to be refrigerated?

They’re best stored at room temperature, but if your kitchen is particularly warm or humid, you can refrigerate them. Bring to room temperature or reheat briefly before serving for the best texture and flavor.

How do I prevent the cookies from sticking when flipping them?

The key is to let them cool for about 10 minutes before turning out and to use a wax paper-covered surface. If any pineapple does stick, just gently pry it from the pan and place it back on the cookie—nobody will ever know!

Final Thoughts

If you want to bring pure sunshine to your dessert table, Pineapple Upside Down Sugar Cookies are the way to go. Their mix of nostalgia, whimsy, and tropical flavor will win over anyone who takes a bite—so don’t wait, gather up those simple ingredients and treat yourself to a batch soon. You deserve a little island-inspired cookie magic!

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