If you’re craving a bite-sized treat that captures all the nostalgic charm of a classic cake but with the delightfully chewy texture of a sugar cookie, Pineapple Upside-Down Sugar Cookies are here to steal your heart. These cookies combine buttery dough with caramelized brown sugar, tangy pineapple, and those iconic maraschino cherries to bring summer’s sunshine right onto your plate, no matter the season. Each cookie looks as dazzling as it tastes, and they’re guaranteed to be a show-stopper at any gathering or simply as a sweet pick-me-up on a busy afternoon.

Pineapple Upside-Down Sugar Cookies Recipe - Recipe Image

Ingredients You’ll Need

This recipe comes together with a handful of pantry staples and a few tropical touches that create an unforgettable flavor. Every ingredient is essential — from the rich butter to the pop of cherry — contributing to that perfect balance of color, moisture, and taste.

Unsalted Butter (1 cup, softened): Brings creamy richness and helps develop that classic sugar cookie crumb.
Granulated Sugar (1¼ cups): Sweetens the dough and gives the cookies their classic chew.
Egg (1 large): Adds structure and helps bind everything together for just the right amount of lift.
Vanilla Extract (2 teaspoons): Enhances all the other flavors with a touch of warmth and comfort.
All-Purpose Flour (2½ cups): The foundation of the dough, giving your cookies their tender body.
Baking Powder (½ teaspoon): Lends a gentle rise for lightness in each bite.
Salt (¼ teaspoon): Balances the sweetness and brightens the fruit flavors.
Crushed Pineapple (1 cup, drained well): Adds juicy tropical flavor — be sure it’s well-drained so your cookies aren’t soggy.
Maraschino Cherries (12, halved): Provides that signature pop of color and a hint of sweet-tartness at the center of each cookie.
Brown Sugar (½ cup): Caramelizes in the oven for a toasty, molasses-rich note that mingles with the pineapple.
Unsalted Butter (2 tablespoons, melted): Helps meld the brown sugar and forms the sticky-sweet base of each cookie.
Nonstick Cooking Spray: Ensures your cookies release easily and maintain that perfect upside-down look.

How to Make Pineapple Upside-Down Sugar Cookies

Step 1: Prep and Preheat

Start by preheating your oven to 350°F. Lightly spray a 12-cup muffin tin with nonstick cooking spray. This not only prevents sticking, but also makes it easy to pop out those gorgeous Pineapple Upside-Down Sugar Cookies with their fruit-topped bottoms perfectly intact.

Step 2: Create the Caramelized Fruit Layer

In a small bowl, stir together the melted butter and brown sugar. Drop about a teaspoon of this mixture into the bottom of each muffin cup. Place a halved maraschino cherry, cut side up, in the center, then add about a tablespoon of drained crushed pineapple on top. This will form that signature golden, fruity layer that’ll eventually show off when the cookies are flipped.

Step 3: Make the Cookie Dough

Cream the softened butter and granulated sugar in a large bowl using a mixer until it’s light and fluffy — think soft clouds. Beat in the egg and vanilla extract so the batter becomes smooth and glossy. In a separate bowl, whisk together the flour, baking powder, and salt, then gradually add these dry ingredients into the creamed mixture, mixing just until combined. You’re aiming for a thick, scoopable dough.

Step 4: Assemble the Cookies

Scoop about two tablespoons of dough, flatten it slightly between your palms, and gently layer it over the pineapple in each muffin cup. Don’t worry if the dough doesn’t reach perfectly to the edges — it’ll spread as it bakes, creating a pillowy lid for that fruity base.

Step 5: Bake to Perfection

Bake for 18 to 22 minutes, or until the cookies are puffed and the edges start turning a light golden brown. Let them cool for 5 minutes in the tin — this little patience step helps the caramelized fruit set. Then, with a confident flip onto a wire rack, watch your Pineapple Upside-Down Sugar Cookies reveal their jewel-toned tops!

How to Serve Pineapple Upside-Down Sugar Cookies

Garnishes

A light dusting of powdered sugar makes these cookies even more inviting, while a little extra drizzle of warm caramel sauce will send pineapple lovers straight over the moon. If you want to double down on the tropical vibes, a tiny sprinkle of toasted coconut on top is both pretty and delicious.

Side Dishes

Keep it simple: a scoop of vanilla ice cream pairs beautifully with the bright, jammy fruit, and a dollop of softly whipped cream adds a cloud-like contrast. For brunch or special tea parties, serve alongside tropical fruit salad or a bright citrusy punch — the cookies truly shine wherever you put them.

Creative Ways to Present

Serve Pineapple Upside-Down Sugar Cookies on a platter studded with extra cherries and pineapple slices for a festive touch. For a special occasion, stack them in a cookie tower, or individually plate with a cherry on the side and a swirl of cream. For a fun twist, tuck them into colorful cupcake liners for grab-and-go treats at summer gatherings.

Make Ahead and Storage

Storing Leftovers

These cookies are at their best the day they’re baked, but you can store leftovers in an airtight container at room temperature for up to two days. The pineapple keeps things moist, so be sure to separate layers with parchment if you’re stacking them to prevent any sticking.

Freezing

To freeze, let the Pineapple Upside-Down Sugar Cookies cool completely, then wrap each cookie tightly in plastic wrap and place in a freezer-safe bag or container. They’ll keep well for up to two months. Thaw at room temperature for the freshest taste and texture.

Reheating

If you prefer a warm cookie, pop one in the microwave for just 10-15 seconds or briefly in a 300°F oven until gently heated. The fruit layer will become a bit gooier and bring those flavors right back to life.

FAQs

Can I use pineapple rings instead of crushed pineapple?

Crushed pineapple is best for this recipe, as it fits perfectly into each muffin cup and ensures you get juicy fruit in every bite. Pineapple rings are a little too large, but you could chop them finely if needed.

What if I don’t have a muffin tin?

A muffin tin creates the cookie’s iconic shape, but in a pinch, you can use ramekins or even a silicone cupcake mold. Just adjust the amount of filling and dough so everything fits nicely together.

How do I keep the bottoms from getting soggy?

Be diligent about draining the crushed pineapple — pressing between paper towels really helps. Soggy bottoms are rare if you remove as much moisture as possible before assembling.

Can I make Pineapple Upside-Down Sugar Cookies dairy-free?

Absolutely! Substitute your favorite plant-based butter for the dairy butter in both the dough and the topping. Just be sure it’s one that bakes well for best results.

Can I double this recipe?

Yes, these cookies double beautifully! Prepare two muffin tins or bake in batches, and you’ll have plenty to share — which is always a good idea with Pineapple Upside-Down Sugar Cookies.

Final Thoughts

I hope you’re as excited as I am to give Pineapple Upside-Down Sugar Cookies a try. There’s just something magical about that first bite, when the buttery cookie meets sweet caramelized fruit. If you’re looking to brighten up your dessert tray or surprise someone with something extra special, these little gems never disappoint. Happy baking!

Pineapple Upside-Down Sugar Cookies Recipe

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4.9 from 12 reviews

Author: admin
Total Time: 40 minutes
Yield: 12 cookies 1x
Diet: Vegetarian

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Description

These Pineapple Upside-Down Sugar Cookies are a delightful twist on the classic dessert. Soft, buttery cookies with a tropical pineapple and cherry topping, they are perfect for any occasion.

Ingredients

Scale

Cookies:

1 cup unsalted butter (softened)
1¼ cups granulated sugar
1 large egg
2 teaspoons vanilla extract
2½ cups all-purpose flour
½ teaspoon baking powder
¼ teaspoon salt

Topping:

1 cup crushed pineapple (drained well)
12 maraschino cherries (halved)
½ cup brown sugar
2 tablespoons unsalted butter (melted)
nonstick cooking spray

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Instructions

Preheat the oven: Preheat the oven to 350°F and lightly spray a muffin tin with nonstick cooking spray.
Prepare the topping: Mix melted butter and brown sugar, spoon into each muffin cup, add a cherry half, and top with drained crushed pineapple.
Make the cookie dough: Cream butter and sugar, add egg and vanilla. In a separate bowl, whisk flour, baking powder, and salt. Combine wet and dry ingredients.
Assemble: Place cookie dough over the pineapple layer in each cup.
Bake: Bake for 18–22 minutes until golden.
Cool and serve: Allow to cool in the pan for 5 minutes, then invert onto a rack to cool completely.