🍍 Pineapple Upside-Down Sugar Cookies: A Tropical Twist on a Classic Treat

There’s something magical about the aroma of freshly baked cookies drifting through your kitchen—especially when those cookies are topped with golden pineapple rings, sweet maraschino cherries, and a warm, buttery brown sugar glaze. These Pineapple Upside-Down Sugar Cookies are the perfect way to bring a taste of the tropics into your home, no matter the season.

Imagine a warm summer day, the sun is shining, and you’re sipping something cold on the porch. These cookies fit that mood perfectly. Or maybe you’re planning a holiday cookie exchange and want to surprise everyone with something unexpected. Inspired by the classic pineapple upside-down cake, this easy cookie version brings the same nostalgic flavor but in a cute, shareable, and bite-sized form.

Let’s dive into the full recipe, baking tips, and inspiration behind this sunny dessert that’s as beautiful as it is delicious.

🌟 Why You’ll Love These Pineapple Upside-Down Sugar Cookies

Tropical and nostalgic: Combines the classic flavors of pineapple upside-down cake with soft, buttery sugar cookies.
Beautiful presentation: Golden pineapple slices and bright cherries create a visually striking treat perfect for parties or gifts.
Easy to make: No complicated steps or fancy equipment—just simple ingredients and straightforward directions.
Perfect for any occasion: Great for summer barbecues, potlucks, holiday cookie trays, or just a weekday treat.

📝 Ingredients You’ll Need

For the Sugar Cookies:

1 cup unsalted butter, softened
1 cup granulated sugar
1 large egg
1 teaspoon vanilla extract
2 ½ cups all-purpose flour
1 teaspoon baking powder
½ teaspoon baking soda
½ teaspoon salt

For the Topping:

1 can (8 oz) pineapple slices, drained (reserve juice for extra flavor if desired)
¼ cup unsalted butter
½ cup brown sugar, packed
Maraschino cherries (one for each cookie)

👩‍🍳 How to Make Pineapple Upside-Down Sugar Cookies

Follow this step-by-step guide to bring these cookies to life.

1. Preheat and Prepare

Preheat your oven to 350°F (175°C) and line two baking sheets with parchment paper. This prevents sticking and helps the cookies bake evenly.

2. Make the Sugar Cookie Dough

In a large mixing bowl, cream together the softened butter and granulated sugar until the mixture becomes light and fluffy. This should take about 3–4 minutes using a hand or stand mixer.

Add the egg and vanilla extract, then mix until fully incorporated.

In a separate bowl, whisk together the flour, baking powder, baking soda, and salt. Gradually add the dry mixture into the wet ingredients, mixing just until combined. Don’t overmix—this keeps your cookies tender!

3. Prepare the Buttery Brown Sugar Topping

In a small saucepan, melt ¼ cup butter and ½ cup packed brown sugar over medium heat. Stir constantly until the mixture becomes bubbly and smooth. This will form the delicious caramelized base under your pineapple and cherry.

4. Assemble the Cookies

Spoon about 1 tablespoon of the brown sugar mixture onto each cookie spot on your baking sheet. Immediately place a pineapple slice over each spoonful, then nestle a maraschino cherry in the center of the pineapple ring.

Using a cookie scoop or tablespoon, gently place 1 tablespoon of sugar cookie dough over the top of each pineapple ring. Lightly press to spread it out and cover most of the fruit (it’s okay if some shows—this adds to the visual appeal!).

5. Bake and Cool

Bake for 12–15 minutes, or until the edges of the cookie dough begin to turn a light golden brown.

Let the cookies cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely. The topping will set slightly as it cools, creating that sticky-sweet glaze we all love.

🍽️ Serving Suggestions

These cookies are delicious warm—just like the cake they’re inspired by—but also wonderful at room temperature. They pair beautifully with:

A scoop of vanilla ice cream
A drizzle of caramel sauce
A cold glass of milk or hot cup of tea

For a festive touch, serve them on a decorative platter garnished with extra pineapple slices or mint leaves.

🛠️ Tips for Success

1. Drain Your Pineapple Well

Too much juice can make the cookie dough slide or become soggy. Be sure to drain your pineapple slices thoroughly and blot with paper towels if needed.

2. Use Room Temperature Butter

This ensures a smooth, even cookie dough. Cold butter won’t cream properly and melted butter will make the dough too soft.

3. Chill If Needed

If your cookie dough is too soft to handle, chill it for 15–20 minutes before scooping onto the pineapple. This helps it hold its shape during baking.

4. Don’t Skip the Parchment Paper

The brown sugar topping can get sticky during baking. Parchment makes cleanup a breeze and prevents sticking or burning.

🌴 The Story Behind the Recipe

This recipe is inspired by pineapple upside-down cake, a dessert that has graced American tables since the early 1900s. Traditionally baked in a skillet or cake pan, the combination of caramelized pineapple and cherries is a nostalgic favorite for many.

These cookies are a modern, portable twist on that classic dessert. Perfect for those who want all the flavor and charm without needing to serve slices or fuss with flipping a cake. They’ve become a favorite in my family for summer gatherings and holiday cookie swaps—and they never fail to impress!

🧁 Variations and Substitutions

Want to switch things up? Here are some ideas:

Mini version: Use pineapple tidbits or crushed pineapple for bite-sized cookies.
Gluten-free: Use a 1:1 gluten-free flour blend suitable for baking.
Add coconut: Sprinkle a bit of shredded coconut on top of the dough before baking for a tropical flair.
Add rum flavor: A splash of rum extract in the cookie dough or brown sugar topping gives a Piña Colada vibe.

🧊 Storage and Make-Ahead Tips

These cookies can be made ahead and stored easily!

Room Temperature: Store in an airtight container for up to 3 days.
Refrigerate: Keep in the fridge for up to 5 days—just bring to room temp before serving.
Freeze: Flash freeze cooled cookies on a baking sheet, then transfer to a zip-top freezer bag. They’ll keep for up to 2 months. Thaw at room temp or warm gently in the oven.

If making for a party, you can also prep the cookie dough and pineapple toppings the night before and assemble just before baking.

📸 Make It Instagram-Worthy

Want your cookies to go viral? Here’s how to level up your food styling:

Use a white or tropical-themed backdrop.
Sprinkle coconut or powdered sugar lightly over the cookies.
Stack a few on a plate with pineapple slices in the background.
Photograph with natural light to highlight that golden caramel glaze.

Tag your creations with #TropicalCookieVibes or #UpsideDownCookies and don’t forget to tag us—we love seeing your baking magic!

💬 Reader Raves

“These were a HUGE hit at our neighborhood potluck. Everyone asked for the recipe!” — Lindsey R.

“Tastes just like pineapple upside-down cake but way more fun to eat. The cherry center is the best part!” — Marcus T.

“My kids loved helping assemble the cookies. It’s now a weekend baking tradition!” — Natalie G.

📌 Final Thoughts

These Pineapple Upside-Down Sugar Cookies bring joy with every bite—bright, sweet, and just a little whimsical. They’re easy to make, hard to resist, and guaranteed to be the most talked-about treat at your next get-together.

Whether you’re chasing a little sunshine in the middle of winter or planning a tropical-themed party, this recipe delivers smiles, flavor, and that irresistible “just one more” feeling.

🍍 Try the Recipe Today!

Ready to bake? Grab your ingredients and treat yourself (and your lucky guests) to these unforgettable cookies. And don’t forget to share this recipe with your fellow cookie lovers. Pin it, post it, or print it—just don’t keep it a secret!

Prep Time: 15 minutes
Cook Time: 15 minutes
Total Time: 30 minutes
Yield: 24 cookies