If you love the nostalgic charm of pineapple upside-down cake but crave something more portable and perfectly bite-sized, this Pineapple Upside-Down Sugar Cookies Recipe is what you’ve been waiting for. Imagine tender sugar cookies crowned with luscious caramelized pineapple slices and bright maraschino cherries, all wrapped in a buttery, brown sugar glaze that gives each bite a sweet and tropical burst of flavor. These treats are not just a feast for your taste buds but also a joy to bake and share with friends or family, making dessert time a sunny celebration any day of the week.

Pineapple Upside-Down Sugar Cookies Recipe - Recipe Image

Ingredients You’ll Need

Simple yet carefully chosen ingredients come together to create the magic in this Pineapple Upside-Down Sugar Cookies Recipe. Each plays its part, from the creamy butter that ensures a tender crumb to the brown sugar glaze that gives a beautiful caramelized touch on top. Let’s look at what you’ll gather before the fun begins.

1 cup unsalted butter, softened: This is the heart of your cookie dough, giving moisture and richness.
1 cup granulated sugar: Sweetens the dough and helps with texture for that classic sugar cookie bite.
1 large egg: Binds all the ingredients, adding structure and a touch of silkiness.
1 teaspoon vanilla extract: Adds a warm, aromatic flavor that complements the tropical notes.
2 ½ cups all-purpose flour: The base of the dough, providing structure and balance.
1 teaspoon baking powder: Helps the cookies rise just enough for a soft, tender texture.
½ teaspoon baking soda: Works with the acidity to give a light lift and slight chewiness.
½ teaspoon salt: Enhances all the flavors and balances sweetness.
1 can (8 oz) pineapple slices, drained (reserve juice): The star ingredient giving fruity juiciness and aroma.
¼ cup unsalted butter (for glaze): Melted with brown sugar to create that perfect caramelized glaze.
½ cup brown sugar, packed: Adds depth with its molasses notes in the topping.
Maraschino cherries (one for each cookie): Adds a pop of color and a classic finishing touch.

How to Make Pineapple Upside-Down Sugar Cookies Recipe

Step 1: Get Your Oven Ready and Prep Baking Sheets

Start by preheating your oven to 350°F (175°C). Line two baking sheets with parchment paper to prevent your cookies from sticking and ensure even baking. Setting up early makes the process smooth and enjoyable.

Step 2: Cream Butter and Sugar Until Fluffy

In a large mixing bowl, cream the softened butter with granulated sugar using a hand mixer or stand mixer. This should take about 3-4 minutes and the mixture will look light and fluffy. This step is key for that melt-in-your-mouth texture.

Step 3: Mix in the Egg and Vanilla

Next, add the large egg and vanilla extract to the creamed butter and sugar. Beat until everything is well combined and smooth. This brings richness and a lovely aroma to your cookie dough.

Step 4: Combine Dry Ingredients

In a separate bowl, whisk together the all-purpose flour, baking powder, baking soda, and salt. This ensures that baking agents are evenly distributed throughout the dough for consistent texture.

Step 5: Gently Incorporate Dry Mix into Wet Ingredients

Gradually add the flour mixture into your butter mixture, stirring gently and just until combined. Over-mixing can toughen cookies, so keep it light to maintain a tender crumb.

Step 6: Prepare the Brown Sugar Pineapple Glaze

In a small saucepan, melt ¼ cup unsalted butter over medium heat. Stir in the packed brown sugar and continue stirring until the mixture is bubbly and smooth, creating a luscious glaze you’ll spoon onto each cookie spot.

Step 7: Layer the Pineapple and Cherries on Your Baking Sheets

Carefully spoon about a tablespoon of the warm butter-brown sugar mixture onto each marked cookie spot on your parchment-lined sheets. Place one pineapple slice on top of this sugary base and press a maraschino cherry right into the center of each slice, ensuring it stays put during baking.

Step 8: Top Each Pineapple Slice with Cookie Dough

Take a tablespoon of cookie dough and gently scoop it over the pineapple slices, covering them slightly but leaving the edges and the cherry visible. This creates the signature upside-down look and ensures the fruit caramelizes nicely beneath the dough.

Step 9: Bake Until Perfectly Golden

Place the trays in your preheated oven and bake for 12 to 15 minutes. Watch as your cookies transform—edges becoming lightly golden signifies they’re ready. This delicate coloring means they’re tender inside but hold just enough structure.

Step 10: Cool and Transfer

Allow the cookies to cool on the baking sheets for about 5 minutes to set, then gently transfer them to a wire rack for complete cooling. This helps prevent breaking and lets the glaze set to a perfect finish.

How to Serve Pineapple Upside-Down Sugar Cookies Recipe

Garnishes

While the maraschino cherry is classic, consider freshly chopped toasted coconut flakes or a sprinkle of finely chopped pistachios for a tropical crunch and an elegant color contrast. A light dusting of powdered sugar can add a pretty, snowy finish and a hint of extra sweetness if you like.

Side Dishes

These cookies pair beautifully with a scoop of vanilla ice cream or a dollop of whipped cream for a cool complement. For beverages, try a tropical punch, iced tea with a lemon wedge, or even a chilled glass of sparkling wine to elevate the dessert experience.

Creative Ways to Present

Serve these cookies on a decorative platter with fresh pineapple slices and mint leaves scattered around for a vibrant presentation. You can also stack them in pretty mason jars for gifting or party favors, making your Pineapple Upside-Down Sugar Cookies Recipe a delightful centerpiece at any gathering.

Make Ahead and Storage

Storing Leftovers

Store your leftover cookies in an airtight container at room temperature for up to 3 days. This keeps them soft and flavorful, though they’re so delicious you might not want any leftovers!

Freezing

If you want to enjoy these cookies later, freeze them in a single layer on a baking sheet, then transfer to a freezer-safe container or bag. They keep well for up to 2 months and thaw quickly at room temperature without losing their charm.

Reheating

To revive the fresh-baked feel, warm your cookies in a 300°F oven for 5 minutes or microwave them for 10 seconds. This will soften the glaze and bring back that just-baked aroma and texture.

FAQs

Can I use fresh pineapple instead of canned?

Absolutely! Fresh pineapple slices will add an even brighter, juicier flavor. Just make sure to drain them well or pat dry so your cookies don’t get soggy.

What if I don’t have maraschino cherries?

You can substitute with fresh cherries, dried cherries, or even small pieces of red candy for the pop of color and sweetness.

Are these cookies gluten-free?

Not as written, since they use all-purpose flour. However, you could experiment with a gluten-free baking blend to make them suitable for gluten sensitivities.

Can I make the dough ahead of time?

Yes! Refrigerate the dough for up to 24 hours before baking. This helps enhance the flavor and makes shaping easier.

How do I make sure the pineapple doesn’t slide off during baking?

Securing the pineapple with the brown sugar butter mixture and placing the cookie dough gently but firmly over it helps keep everything in place. Avoid pressing too hard so the layers stay distinct but connected.

Final Thoughts

This Pineapple Upside-Down Sugar Cookies Recipe is one of those joyful discoveries that combines a beloved classic with the convenience and charm of cookies. Whether you’re baking for a party, a sweet snack, or just to brighten up your day, these cookies bring sunshine to your kitchen and smiles to everyone who tries them. I can’t wait for you to try this recipe and make it your own—happy baking!