Pineapple Upside-Down Cookies Recipe Easy Tropical Dessert

The buttery smell of caramelized pineapple baking in the oven is something you’ll never forget. These Pineapple Upside-Down Cookies are like mini tropical desserts that pack all the flavor of the classic cake into portable, bite-sized treats. I first made these for a backyard barbecue, and let me tell you—they didn’t last long! Whether it’s the chewy texture, the sweet pineapple topping, or the subtle coconut undertone, these cookies are pure sunshine in every bite.

If you’re craving something unique but easy to make, this recipe is perfect. It combines the nostalgia of a pineapple upside-down cake with the simplicity of cookies. Plus, it’s a great way to wow your guests without spending hours in the kitchen. Let’s dive into this fun twist on a classic dessert!

Why You’ll Love This Recipe

• Quick & Easy: These cookies come together in under an hour, making them perfect for busy bakers.
• Unique and Fun: They’re a creative spin on a traditional pineapple upside-down cake, but in cookie form!
• Crowd-Pleaser: Kids and adults alike love the tropical flavor and adorable presentation.
• Perfect for Any Occasion: Whether it’s a summer picnic, holiday party, or just a sweet treat at home, these cookies fit the bill.
• Irresistible Flavor: The buttery cookie base paired with caramelized pineapple and brown sugar is a match made in heaven.

What sets this recipe apart is the attention to detail—like slightly browning the pineapple for extra flavor and adding just a hint of coconut extract to bring out the tropical vibes. Trust me, this isn’t just another cookie recipe; it’s a mini vacation for your taste buds!

What Ingredients You Will Need

This recipe uses simple ingredients that come together to create a tropical masterpiece. Most of them are pantry staples, with a few fresh additions for that signature flavor.

• Unsalted butter, softened: Adds richness and softness to the cookies.
• Granulated sugar: Sweetens the cookie base perfectly.
• Brown sugar: For the caramelized topping—it’s what gives that irresistible golden flavor.
• Eggs, room temperature: Helps bind the dough and adds moisture.
• Vanilla extract: Enhances the overall flavor.
• Coconut extract: Optional but recommended for a tropical flair.
• All-purpose flour: The base of the cookie dough.
• Baking powder: Gives the cookies a little lift.
• Salt: Balances the sweetness.
• Fresh pineapple, diced: The star ingredient! Look for ripe, juicy fruit for maximum flavor.
• Maraschino cherries: Optional but adds a pop of color and sweetness.

The best part? You can easily swap fresh pineapple for canned if you’re in a pinch, and the coconut extract is entirely optional if you’re not a fan of coconut.

Equipment Needed

You don’t need any fancy equipment to make these cookies! Here’s what you’ll need:

• Mixing bowls: One for wet ingredients, one for dry.
• Electric mixer: For creaming the butter and sugar—hand mixers work too!
• Cookie scoop: Helps portion the dough evenly.
• Baking sheets: Lined with parchment paper for easy cleanup.
• Small frying pan: To caramelize the pineapple.

If you don’t have a cookie scoop, a tablespoon will work just fine for portioning out the dough. Also, make sure your baking sheets are sturdy to ensure even baking.

Preparation Method

Let’s break this down step-by-step so you can achieve cookie perfection:

1. Preheat your oven: Set it to 350°F (175°C). Line your baking sheets with parchment paper.
2. Prepare the topping: In a small frying pan, melt 2 tablespoons of butter over medium heat. Add the diced pineapple and 1/4 cup of brown sugar. Cook until the pineapple starts to caramelize (about 5 minutes). Set aside to cool.
3. Make the cookie dough: In a large mixing bowl, cream 1/2 cup of softened butter with 1/2 cup of granulated sugar and 1/4 cup of brown sugar using an electric mixer. Beat until fluffy.
4. Add the wet ingredients: Mix in 1 egg, 1 teaspoon of vanilla extract, and 1/2 teaspoon of coconut extract (if using).
5. Incorporate dry ingredients: In a separate bowl, whisk together 1 1/4 cups of all-purpose flour, 1/2 teaspoon of baking powder, and 1/4 teaspoon of salt. Gradually add this to the wet ingredients, mixing until just combined.
6. Portion the dough: Scoop out tablespoons of dough and place them on the prepared baking sheets about 2 inches apart.
7. Add the topping: Flatten each ball of dough slightly, then spoon a bit of the caramelized pineapple onto each cookie. Press a maraschino cherry into the center of the pineapple topping, if desired.
8. Bake: Bake for 12-15 minutes, or until the edges are golden brown. Allow cookies to cool on the baking sheet for 5 minutes before transferring to a wire rack.

And there you have it—your very own batch of Pineapple Upside-Down Cookies!

Cooking Tips & Techniques

• Don’t overmix the dough: Overmixing can lead to tough cookies. Mix just until the flour is incorporated.
• Use ripe pineapple: Fresh pineapple that’s sweet and juicy will caramelize beautifully and provide the best flavor.
• Keep an eye on the topping: When caramelizing the pineapple, don’t let it burn. Stir often and reduce the heat if necessary.
• Cool cookies completely: The topping will set better as the cookies cool, making them easier to handle.

If you accidentally make the dough too sticky, chilling it in the fridge for 30 minutes will make it easier to scoop.

Variations & Adaptations

• Gluten-Free Option: Substitute all-purpose flour with a gluten-free baking blend.
• Seasonal Twist: Swap pineapple for peaches or mangoes during summer months.
• Flavor Boost: Add a pinch of cinnamon or nutmeg to the cookie dough for a warm, spiced note.
• Dairy-Free Version: Use vegan butter and skip the egg—replace it with a flaxseed egg or applesauce.

Personally, I’ve tried these with mango instead of pineapple, and they were just as delicious—a tropical win!

Serving & Storage Suggestions

These cookies are best served slightly warm, but they’re just as delicious at room temperature. Here are some serving and storage tips:

• Serving: Pair them with a scoop of vanilla ice cream or a drizzle of caramel sauce for an extra decadent dessert.
• Storage: Keep cookies in an airtight container at room temperature for up to 3 days.
• Freezing: These freeze well! Store in a freezer-safe container for up to 2 months. Thaw at room temperature before serving.
• Reheating: Pop them in the microwave for 10-15 seconds to revive the warm, caramelized topping.

The flavors tend to deepen after a day, so don’t hesitate to make them ahead of time for parties or gatherings!

Nutritional Information & Benefits

Here’s a rough estimate per cookie (based on a batch of 24):

• Calories: 120
• Fat: 5g
• Carbohydrates: 18g
• Protein: 1g
• Sugar: 13g

Pineapple is rich in vitamin C and antioxidants, making these cookies a sweet treat with a touch of healthfulness. Of course, moderation is key!

Conclusion

These Pineapple Upside-Down Cookies are the perfect tropical treat for any occasion. Whether you’re hosting a summer party or just looking to brighten up a rainy day, these cookies bring sunshine to your kitchen. I love how versatile and fun they are—you can even get the kids involved in decorating with cherries!

Give this recipe a try and let me know how it turns out! Share your creations in the comments below or tag me on Instagram if you add your own twist. Happy baking, and I hope these cookies bring a little tropical joy to your life!

FAQs

Can I use canned pineapple instead of fresh?

Yes! Just make sure to drain it well to avoid extra moisture in the topping.

Do I need to chill the cookie dough?

Not necessarily, but if the dough feels sticky, chilling it for 30 minutes will make it easier to work with.

Can I make these cookies ahead of time?

Absolutely! Store them in an airtight container, and they’ll stay fresh for up to 3 days.

What’s the best way to caramelize the pineapple?

Cook it over medium heat with butter and brown sugar, stirring often, until it turns golden and fragrant.

Can I skip the maraschino cherries?

Of course! They’re mainly for decoration and an extra burst of sweetness, but the cookies are just as delicious without them.

Print