If you’re on the hunt for a fun, nostalgic, and utterly irresistible treat, the Pineapple Upside Sugar Cookies Recipe is your new best friend in the kitchen. Combining the gooey decadence of brown sugar and butter caramel glaze with the tropical zing of canned pineapple and the classic cherry on top, these cookies deliver an unforgettable bite every single time. Soft, tender sugar cookie dough hugs the warm caramelized pineapple and cherry, creating a delightful marriage of flavors that’s perfect for any occasion. Trust me, once you make this Pineapple Upside Sugar Cookies Recipe, your cookie game will never be the same!

Pineapple Upside Sugar Cookies Recipe - Recipe Image

Ingredients You’ll Need

All you need are a handful of simple, everyday ingredients that come together to create the magic of this Pineapple Upside Sugar Cookies Recipe. Each ingredient plays an important role: the butter and sugar give richness and sweetness, sour cream adds moisture and tenderness, while the pineapple and cherries add that signature fruity burst and vibrant color.

Butter (1 cup, room temperature): The base fat that ensures your cookies are soft and perfectly tender.
Granulated sugar (1 ½ cups): Sweetens and helps create a light, fluffy dough.
Eggs (2): Bind everything together and add richness.
Vanilla extract (2 teaspoons): Adds a warm, comforting depth of flavor.
Sour cream (½ cup): Keeps the cookie moist with a slight tangy note that balances sweetness.
All-purpose flour (3 cups): The structure of your cookies, giving them form and a tender bite.
Baking powder (1 teaspoon): Helps your cookies rise just enough for a light texture.
Cornstarch (1 teaspoon): Adds extra tenderness to the cookie dough.
Salt (½ teaspoon): Enhances the flavors and balances the sweetness.
Canned pineapple slices (13): The star of the show bringing juicy tropical sweetness.
Maraschino cherries (13): Classic bright red cherries for that festive, fun look.
Melted butter (½ cup): To mix with brown sugar and create a luscious caramel glaze.
Light brown sugar (1 cup packed): Provides deep caramel notes that perfectly complement pineapple.

How to Make Pineapple Upside Sugar Cookies Recipe

Step 1: Preheat the Oven and Prep the Pan

Start by heating your oven to a cozy 350°F. While that warms up, grab your mini round cake pan – a USA Pan is ideal – and set it aside. This pan is crucial because it helps the cookies bake evenly and hold their charming shape.

Step 2: Mix the Cookie Dough

Next, get a large mixing bowl and cream together the softened butter and granulated sugar until they’re light and fluffy, which takes about 3 minutes with a hand or stand mixer. Then, add in the eggs, vanilla extract, and sour cream, mixing until everything is beautifully combined. Finally, stir in the flour, baking powder, cornstarch, and salt just until the dough comes together — don’t overmix or it could get tough!

Step 3: Prepare the Brown Sugar Glaze

In a separate bowl, whisk your melted butter and packed brown sugar until you have a smooth, glossy glaze. This is what turns the bottom of your cookies into a caramelized, sticky-sweet wonder that pairs perfectly with the pineapple.

Step 4: Assemble the Cookies

Now for the fun part: drop about a tablespoon of that brown sugar glaze into each cavity of your prepared pan. Place one pineapple slice on top of the glaze, and pop a maraschino cherry right in the center of the pineapple. Then, scoop about three tablespoons of cookie dough and gently flatten it on top, covering the fruit completely but keeping the shape intact.

Step 5: Bake and Cool

Pop those beauties into the oven and bake for around 25 minutes, or until the cookie edges turn golden and you see the brown sugar bubbling up around the sides. Let the cookies cool in the pan for about 10 minutes, then carefully turn them out onto wax paper. If your pineapple shifted, just nudge it back into place. Let the cookies cool completely before you dive in — the flavors and textures are best once fully set.

How to Serve Pineapple Upside Sugar Cookies Recipe

Garnishes

For an extra touch of elegance or festivity, dust the cookies lightly with powdered sugar right before serving. You can also drizzle a little bit of melted white chocolate or sprinkle toasted coconut flakes on top to echo the tropical vibe.

Side Dishes

Pair these cookies with a scoop of vanilla ice cream or a dollop of whipped cream for an indulgent dessert experience. They also go splendidly with a fresh fruit salad or a hot cup of tea or coffee, making them perfect for afternoon treats or party plates.

Creative Ways to Present

Try arranging the cookies on a pretty platter with fresh pineapple wedges and extra cherries scattered around for a show-stopping presentation. These also make fantastic individual gifts when wrapped in cellophane with a colorful ribbon – perfect for holiday or summer parties!

Make Ahead and Storage

Storing Leftovers

If you have leftovers, store your Pineapple Upside Sugar Cookies Recipe in an airtight container at room temperature. They’ll stay fresh and delicious for 2 to 3 days, perfect for quick snacks or unexpected guests.

Freezing

You can freeze these cookies either before or after baking. To freeze dough, shape and assemble the cookies as directed, then wrap your pan tightly in plastic wrap and aluminum foil before freezing for up to 3 months. For baked cookies, cool completely, then freeze in a freezer-safe container layered with parchment paper to prevent sticking.

Reheating

When you’re ready to enjoy frozen baked cookies, simply thaw them at room temperature for about an hour, or warm them gently in a 300°F oven for 5 to 7 minutes to refresh that caramel glaze and soft texture. Cookies made from frozen dough can be baked directly from frozen—just add a few extra minutes to the baking time.

FAQs

Can I use fresh pineapple instead of canned for the Pineapple Upside Sugar Cookies Recipe?

Fresh pineapple can be used, but be sure to drain it well and pat dry to avoid excess moisture. Canned pineapple slices are softer and sweeter, which helps with the cookie’s texture and caramelization.

What can I substitute for sour cream in this recipe?

If you don’t have sour cream on hand, plain Greek yogurt works beautifully as a substitute and will maintain the cookie’s moist tenderness with a similar tangy flavor.

Can I make these cookies gluten-free?

Yes! Substitute the all-purpose flour with a gluten-free flour blend that includes xanthan gum for structure. The texture may vary slightly but the flavor remains delightful.

Is it necessary to use a mini round cake pan?

While a mini round cake pan helps achieve the perfect cookie shape, you can use a standard muffin tin as an alternative. The cookies might bake a little differently, so watch the baking time closely.

How do I prevent the pineapple from sticking to the pan?

Ensure you grease your pan well before layering with the brown sugar glaze. The butter and sugar help create a natural release, but a light coating of non-stick spray or butter ensures the cookies pop out easily.

Final Thoughts

This Pineapple Upside Sugar Cookies Recipe is a delightful fusion of classic flavors and playful presentation that’s sure to become a staple in your baking repertoire. Whether you’re treating your family or bringing something special to a gathering, these cookies never fail to spark smiles and happy taste buds. I can’t wait for you to try them and make your kitchen smell like a tropical bakery!