Irresistible Pineapple Upside Down Cookies You Have to Try

If you’re looking to bring a tropical twist to your cookie game, look no further than these Pineapple Upside Down Cookies. Inspired by the classic pineapple upside-down cake, these charming little treats capture all the magic of that nostalgic dessert—sweet caramelized pineapple, buttery richness, and a hint of cherry brightness—all in handheld cookie form. Whether you’re entertaining guests, making a summer dessert, or craving a new tropical baking idea, these cookies will win hearts in a single bite.

They’re soft, flavorful, visually stunning, and best of all—surprisingly easy to make. Each cookie features a mini pineapple slice and cherry nestled in a pool of golden brown sugar caramel, baked into a soft, cake-like cookie base. The result? A perfectly portioned dessert that brings smiles with every bite.

Let’s explore why this recipe deserves a place in your baking rotation and how to master it from start to finish.

Save

Why Pineapple Upside Down Cookies Are a Must-Bake Treat

These cookies combine everything you love about a traditional pineapple upside-down dessert with the convenience and portability of a cookie. They’re festive enough for parties, quick enough for weekday treats, and flavorful enough to satisfy any sweet craving.

What sets them apart is their perfect balance: the rich vanilla cookie base is light and fluffy, while the brown sugar topping caramelizes during baking, giving each cookie its own little burst of juicy pineapple sweetness. They’re also versatile—perfect for summer BBQs, tropical-themed parties, holidays, or just a fun weekend baking session.

If you’ve been looking for more creative pineapple baked goods, this recipe is your golden ticket.

Who Will Love These Tropical-Inspired Pineapple Cookies?

These cookies are for:

• Fans of pineapple upside-down cake looking for a fresh take
• Anyone seeking new and easy plant-based dessert ideas (this can be adapted easily)
• Home bakers who love experimenting with classic recipes
• People who enjoy soft, moist cookies with fruity flair
• Anyone who wants something new for cookie exchanges or gift baskets

They’re also great for kids—fun to look at, fun to eat, and naturally sweet with real fruit.

Ingredients for Pineapple Upside Down Cookies (With Measurements)

Here’s everything you’ll need to make 16–18 cookies:

For the Topping:

• 1/3 cup unsalted butter, melted
• 2/3 cup light brown sugar, packed
• 8–9 pineapple rings (fresh or canned in juice)
• 8–9 maraschino cherries, halved

For the Cookie Dough:

• 1/2 cup unsalted butter, softened
• 1/2 cup granulated sugar
• 1/3 cup light brown sugar, packed
• 1 large egg
• 1 teaspoon vanilla extract
• 1 1/2 cups all-purpose flour
• 1/2 teaspoon baking powder
• 1/4 teaspoon baking soda
• 1/4 teaspoon salt
• 2 tablespoons reserved pineapple juice

This recipe blends pantry staples with juicy, tropical fruit for a balanced, flavorful treat.

Recommended Kitchen Tools for Baking Pineapple Cookies

To make this recipe successfully, gather these tools:

• Mini muffin pan (regular muffin tin works too)
• Mixing bowls
• Hand mixer or stand mixer
• Measuring cups and spoons
• Rubber spatula
• Small cookie scoop or spoon
• Cooling rack

You’ll also want a small sharp knife for trimming the pineapple rings into smaller circles to fit the tins.

Step-by-Step: How to Make Pineapple Upside Down Cookies

1. Prep Your Pan
   Preheat your oven to 350°F (175°C). Grease a mini muffin tin well to prevent sticking.
2. Create the Topping
   In a small bowl, mix melted butter and brown sugar. Place about 1 teaspoon of this mixture into each muffin cup.
3. Add Fruit
   Trim pineapple rings to fit each cup, then place a pineapple piece over the brown sugar mix. Add half a maraschino cherry in the center.
4. Mix the Cookie Dough
   In a large bowl, cream softened butter, white sugar, and brown sugar until light and fluffy. Beat in the egg and vanilla extract. Add flour, baking powder, baking soda, and salt. Mix until just combined, then stir in the pineapple juice.
5. Spoon the Dough
   Drop spoonfuls of dough over the fruit, filling each cup about 3/4 full. Smooth the tops with your fingers or a spoon.
6. Bake
   Bake for 14–16 minutes, or until edges are golden and centers are set.
7. Cool and Invert
   Let cookies cool in the pan for 5–7 minutes, then carefully invert onto a cooling rack or parchment paper. Tap the pan gently if needed.
8. Serve and Enjoy!
   Serve warm or cooled. The caramelized tops are irresistible.

Save

Pineapple Upside Down Cookies Tips for Perfect Texture and Flavor

• Use room-temperature ingredients for smooth mixing and even baking.
• Don’t overmix the dough—it should be soft but not sticky.
• Choose canned pineapple in juice for natural sweetness and moisture.
• Drain fruit well to avoid soggy tops or runny caramel.
• Use a nonstick pan or parchment liners for easy release.

These small touches make a big difference in cookie quality and presentation.

Common Baking Mistakes to Avoid With Upside Down Cookies

• Forgetting to grease the pan well—this is key for release.
• Using too much topping—it can overflow and burn.
• Skipping the cooling time—they’ll break apart if removed too soon.
• Using fruit in syrup—juice is better for balance and baking.

Paying attention to these details helps you avoid common cookie fails.

Delicious Variations on the Classic Pineapple Cookie Recipe

Love the idea and want to get creative? Try these twists:

• Swap pineapple for mango or peach slices for a tropical remix
• Use coconut extract in the dough for an island-inspired flair
• Add crushed macadamia nuts to the cookie base
• Try pineapple upside-down cake cookies with mini cake molds for a cakeier version
• Use fresh pineapple chunks for a more vibrant, tangy flavor

Explore your favorite pineapple dessert ideas and adapt accordingly!

How to Serve and Present Your Pineapple Upside Down Cookies

These cookies look fantastic with minimal effort, but here are a few extra tips:

• Plate on a white or tropical-themed platter for contrast
• Garnish with fresh mint or a dusting of powdered sugar
• Serve warm with a scoop of coconut or vanilla ice cream
• Stack in clear gift boxes for tropical-themed party favors

They make perfect additions to dessert bars, picnics, or beach-themed events.

Creative Ideas for Using Fresh Pineapple in Dessert Recipes

Fresh pineapple adds brightness and texture to so many baked goods. If you have leftovers, try using them in:

• Peach pineapple sorbet
• Tropical muffins or upside-down mini cakes
• Fresh pineapple salsa for tacos
• Blended smoothies or popsicles
• Homemade fruit tarts or crumble bars

These are great ways to use up extra pineapple while experimenting with new flavors.

How to Store and Freeze Pineapple Baked Goods Properly

To store:

• Keep cookies in an airtight container at room temperature for up to 3 days.
• If refrigerating, separate layers with parchment to avoid sticking.

To freeze:

• Let cookies cool completely. Wrap individually in plastic, then place in a zip-top freezer bag.
• Freeze for up to 2 months. Thaw at room temperature or warm in the microwave for 10–15 seconds.

Proper storage ensures your cookies stay soft and moist—even days later!

Pairing Ideas: What to Serve With Pineapple Upside Down Cookies

These cookies pair beautifully with:

• Tropical teas like iced honeydew mint tea
• Fruit-infused sparkling water or lemonade
• Light meals such as cucumber blueberry feta salad
• Other fruity desserts like lemon blueberry bread

Keep the menu bright and refreshing to complement their fruity flavor.

Save

Frequently Asked Questions About Pineapple Upside Down Cookies

Can I use fresh pineapple instead of canned?
Yes! Just slice thin and remove any hard core bits. Pat dry before using.

What if I don’t have a mini muffin tin?
Use a regular muffin tin and double the fruit pieces per cup.

Can I make them ahead of time?
Yes, but they taste best the day of. You can prepare and refrigerate dough in advance.

Are these cookies freezer-friendly?
Absolutely—just follow the freezing tips mentioned above.

Do I need to flip them out of the pan?
Yes, flipping them gives you the signature caramelized top and makes for beautiful presentation.

Conclusion and Call to Action

These Pineapple Upside Down Cookies offer all the nostalgic flavor of the classic dessert—reimagined into a fun, portable treat that’s perfect for any season. With golden caramelized pineapple, juicy cherries, and a soft buttery base, they’re sure to steal the spotlight wherever they go.

Looking for more tropical baking ideas or a unique addition to your dessert table? This is the recipe to bookmark and return to again and again.

Tried it? Share the recipe with friends, leave a comment with your twist, and don’t forget to subscribe to the blog for more fun, fruity bakes like this one!

Print