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Indulge in Pineapple Upside Sugar Cookies That Wow!

Published: Oct 7, 2025 by Julie Chen · This post may contain affiliate links · Leave a Comment

As I stood in my kitchen, the sweet scent of crushed pineapple wafted through the air, transporting me to a sun-kissed tropical paradise. These Pineapple Upside Sugar Cookies are a delightful twist on the classic upside-down cake, combining vibrant tropical flavors into a soft, chewy cookie that's bound to become a favorite. With their quick prep time and the option for gluten-free substitutions, these cookies make a perfect companion for summer gatherings or a cozy treat just for you. Whether you enjoy them alone or share them with family and friends, each bite expands the joy of homemade goodness. Are you ready to take your cookie game to a whole new tropical level?

Pineapple Upside Sugar Cookies

Why are Pineapple Upside Sugar Cookies a Must-Try?

Tropical Bliss: Each bite transports you to a sunny paradise, bursting with crushed pineapple and a hint of coconut.
Quick & Easy: These cookies come together in no time, making them perfect for unexpected guests or a last-minute treat.
Customizable Delight: Feel free to swap in favorite toppings or go gluten-free with a simple flour substitution.
Crowd-Pleasing Treat: Ideal for summer parties, bake sales, or cozy family gatherings, they’re sure to impress anyone who tries them.
Nostalgic Flavor: Enjoy the comforting memories of pineapple upside-down cake all wrapped up in a delightful cookie!

Pineapple Upside Sugar Cookies Ingredients

For the Cookie Dough
• Unsalted Butter – This key fat gives a rich, buttery flavor; ensure it's at room temperature for easy creaming.
• Granulated Sugar – Adds sweetness and helps fluff the butter, creating a nice texture.
• Large Egg – Binds the ingredients and provides moisture for that soft, chewy bite.
• Vanilla Extract – Enhances the flavor profile with warm, inviting notes.
• All-Purpose Flour – Provides the cookie's structure; swap for a gluten-free blend for an alternative.
• Baking Powder – A leavening agent that ensures lightness in every cookie.
• Salt – Balances the sweetness and elevates the overall flavor experience.

For the Tropical Twist
• Crushed Pineapple – Infuses fruity flavor and moisture; be sure to drain well to avoid a soggy dough.
• Brown Sugar – Helps create a caramelized coating that mirrors the rich flavor of pineapple upside-down cake.
• Shredded Coconut – Adds texture and a touch of sweetness, but feel free to omit if you're not a fan.

For Optional Toppings
• Maraschino Cherries (optional) – Brightens the cookies with color and a hint of cherry flavor, perfect for a fun finish.

Now that we've gathered all the Pineapple Upside Sugar Cookies ingredients, let's get ready to create a tropical treat that will wow your taste buds!

Step‑by‑Step Instructions for Pineapple Upside Sugar Cookies

Step 1: Preheat the Oven
Begin by preheating your oven to 350°F (175°C). As it warms up, line your baking sheets with parchment paper to ensure that your Pineapple Upside Sugar Cookies won’t stick. This preparation not only simplifies cleanup later but also helps achieve a perfectly baked cookie with golden edges.

Step 2: Cream the Butter and Sugar
In a mixing bowl, place your softened unsalted butter and granulated sugar. Beat them together on medium speed for 2 to 3 minutes until the mixture is light, fluffy, and slightly pale in color. This step is crucial, as the air incorporated will help your cookies rise beautifully, creating that delightful texture.

Step 3: Add Wet Ingredients
Next, crack in a large egg and pour in the vanilla extract. Beat the mixture on low speed until everything is well combined, ensuring a smooth consistency without overmixing. The warm aroma of vanilla will begin to fill your kitchen, hinting at the delicious Pineapple Upside Sugar Cookies to come!

Step 4: Whisk the Dry Ingredients
In a separate bowl, whisk together the all-purpose flour, baking powder, and salt until evenly mixed. This step aerates the dry ingredients, ensuring that your cookies rise evenly and taste fantastic. Mixing them separately helps avoid clumps of baking powder in your batter.

Step 5: Combine the Mixtures
Gradually add the dry ingredients to the wet mixture, stirring gently with a spatula until just combined. Be careful not to overmix, as this can lead to tough cookies. You want the dough to remain soft and slightly sticky to create the chewy texture of these delightful Pineapple Upside Sugar Cookies.

Step 6: Fold in Pineapple and Coconut
Now, it’s time to fold in the well-drained crushed pineapple and shredded coconut, if using. Carefully incorporate them into the dough until evenly distributed, which introduces that tropical flavor. The chunks of pineapple will provide moisture and sweetness, making every bite a delicious treat.

Step 7: Prepare the Brown Sugar Coating
In a small bowl, mix together the brown sugar with 1 to 2 teaspoons of flour, creating a coating that will give your cookies a beautiful caramelized finish. This step mimics the rich top layer of a traditional pineapple upside-down cake and adds an extra layer of sweetness.

Step 8: Portion and Coat the Dough
Using a tablespoon, scoop out portions of your cookie dough and roll them into balls in your hands. Roll each ball in the brown sugar mixture until fully coated. This ensures that those delicious Pineapple Upside Sugar Cookies have a sweet and crispy outer layer when baked, enhancing their appeal.

Step 9: Arrange and Flatten Cookies
Place the coated dough balls on the prepared baking sheets, spaced about 2 inches apart. Lightly flatten each ball with your palm to form a thicker disk shape. This helps them bake evenly, allowing for a soft center and slightly crispy edges—a perfect complement to the chewy texture.

Step 10: Optional Cherry Topping
For an extra pop of color and flavor, gently press a maraschino cherry into the center of each cookie. This little addition not only brightens up the presentation but also adds a delightful cherry burst that enhances the tropical theme of your Pineapple Upside Sugar Cookies.

Step 11: Bake to Perfection
Slide the baking sheets into the preheated oven and bake for 12 to 15 minutes. Keep an eye on them; you want the edges to turn golden brown while the centers remain soft and chewy. The aroma that fills your kitchen will make it hard to wait!

Step 12: Cool Before Serving
Once baked, remove the cookies from the oven and let them cool on the baking sheets for 5 minutes. This allows them to set. Afterward, transfer them to a wire rack to cool completely. Once cooled, these Pineapple Upside Sugar Cookies are ready to be enjoyed, offering a tropical taste in every bite!

Pineapple Upside Sugar Cookies

Make Ahead Options

These Pineapple Upside Sugar Cookies are perfect for meal prep enthusiasts seeking to maximize their time without sacrificing flavor! You can prepare the cookie dough up to 24 hours in advance by mixing all ingredients and storing it in an airtight container in the refrigerator. To maintain quality, ensure the crushed pineapple is well-drained to avoid sogginess. When you're ready to bake, simply roll the chilled dough into balls, coat them in the brown sugar mixture, and bake as directed. Alternatively, you can bake the cookies and store them in an airtight container at room temperature for up to 3 days, ensuring you can enjoy fresh, tropical cookies on demand!

What to Serve with Pineapple Upside Sugar Cookies

As you indulge in the sweet, tropical delight of these cookies, consider these perfect pairings to create a memorable meal experience.

  • Creamy Coconut Ice Cream: A scoop of this velvety treat echoes the coconut notes of the cookies, making for a tropical dessert duo.
  • Tropical Fruit Salad: A mix of fresh fruits like mango, kiwi, and strawberries adds brightness and a refreshing contrast to the sugary cookies.
  • Coconut Milk Smoothie: A chilled blend of coconut milk, banana, and ice creates a creamy drink that complements the cookie's tropical theme.
  • Sweet Tea with Lime: The refreshing citrus notes of lime-infused sweet tea balance the sweetness of the cookies, making for a delightful beverage pairing.
  • Lime Zest Glaze: Drizzle a simple glaze made from powdered sugar and lime juice over the cookies for an added citrusy burst that ties everything together.
  • Maraschino Cherry Topping: If you didn’t add cherries to the cookies, serve them on the side for a fun garnish that enhances the cookie experience.
  • Chocolate-Covered Pineapple Bites: For those who crave a chocolate contrast, these sweet treats make an exciting addition alongside your cookies.
  • Coconut Macaroons: These chewy bites offer another coconut-infused dessert option, creating a delightful dessert spread that's bound to impress.
  • Sparkling Water with Mint: The fizz and freshness of mint-infused sparkling water cleanse the palate and refresh your senses after each delightful bite.

Pineapple Upside Sugar Cookies Variations

Feel free to get creative and customize your Pineapple Upside Sugar Cookies to suit your tastes and dietary needs!

  • Dairy-Free: Replace unsalted butter with coconut oil or a vegan butter substitute to keep the tropical flavors alive without dairy.
  • Nutty Addition: Swap shredded coconut for chopped macadamia nuts for a delightful crunch that pairs beautifully with the pineapple.
  • Spicy Kick: Add a pinch of cayenne pepper or chopped jalapeños for a surprising heat twist that complements the sweetness.
  • Lime Zest Boost: Mix in some lime zest to enhance the tropical flavor profile, bringing a bright, citrusy freshness to every bite.
  • Gluten-Free Option: Substitute all-purpose flour with a 1:1 gluten-free blend for a gluten-free cookie that everyone can enjoy.
  • Chocolate Drizzle: Drizzle melted dark chocolate over cooled cookies for a rich contrast to the tropical flavors that’s purely indulgent.
  • Coconut Cream Center: Sandwich two cookies with coconut cream or whipped topping for a dreamy tropical treat that feels like a dessert delight.
  • Fruit Medley: Incorporate finely chopped cherries or mango along with the pineapple for a vibrant fruit medley in your cookies.

By experimenting with these variations, you can truly make these Pineapple Upside Sugar Cookies your own! Perhaps even explore how they pair with different dips, like a fluffy coconut frosting!

Expert Tips for Pineapple Upside Sugar Cookies

Drain Pineapple Well: Avoid overly moist dough by ensuring the crushed pineapple is thoroughly drained before adding it to the mix.

Chill the Dough: If your dough feels too soft, chill it for about 30 minutes. This helps in shaping and results in firmer cookies.

Avoid Overmixing: Mix until just combined when incorporating dry ingredients; overmixing can lead to tough cookies instead of soft, chewy Pineapple Upside Sugar Cookies.

Customize Toppings: Feel free to swap shredded coconut with your favorite nuts or chocolate chips to make the recipe your own!

Watch Baking Time: Keep a close eye while baking; remove cookies when the edges are golden to ensure a soft and chewy center.

Create a Glaze: For a finishing touch, mix powdered sugar with pineapple juice to drizzle over the cooled cookies for added sweetness and a fun presentation!

How to Store and Freeze Pineapple Upside Sugar Cookies

Room Temperature: Keep cookies in an airtight container for up to 3 days to maintain their soft and chewy texture. Place parchment paper between layers to prevent sticking.

Fridge: If you want them to last a bit longer, store the cookies in the fridge for up to a week. Just remember to seal them well!

Freezer: For longer storage, these Pineapple Upside Sugar Cookies freeze beautifully. Store in a freezer-safe container for up to 2 months. Thaw at room temperature before enjoying.

Reheating: To revive the cookies, heat them in the microwave for about 10-15 seconds or in a preheated oven at 350°F (175°C) for a few minutes until warm. Enjoy the tropical goodness again!

Pineapple Upside Sugar Cookies

Pineapple Upside Sugar Cookies Recipe FAQs

How do I choose ripe pineapple for this recipe?
Absolutely! When selecting a fresh pineapple, look for one that has a sweet aroma at the base. The skin should be golden-yellow with a little give when gently pressed. Avoid any dark spots or overly soft areas. If you opt for canned pineapple, make sure it’s packed in juice or light syrup, and drain it well to avoid excess moisture in your cookie batter.

What is the best way to store Pineapple Upside Sugar Cookies?
Very! To keep these cookies fresh, store them in an airtight container at room temperature for up to 3 days. You can place parchment paper between layers to prevent them from sticking to each other. If you’d like to extend their freshness, you can also refrigerate them for up to a week!

Can I freeze Pineapple Upside Sugar Cookies?
Yes, you can! To freeze, place the cooled cookies in a single layer on a baking sheet and freeze until firm. Then, transfer them to a freezer-safe container or a resealable bag, layering parchment paper between the cookies. They’ll keep well for up to 2 months. When you're ready to enjoy, thaw them at room temperature or warm them slightly in the microwave for 10-15 seconds!

How can I troubleshoot if my cookies are too moist?
If you find your cookies are turning out too moist, it might be due to excess liquid from the pineapple. I recommend ensuring that the crushed pineapple is thoroughly drained to prevent soggy dough. If the dough feels too soft, try chilling it in the fridge for about 30 minutes before baking. This will give the cookies a firmer texture!

Are there any dietary considerations for these cookies?
Absolutely! If you have gluten sensitivities, you can easily make these Pineapple Upside Sugar Cookies gluten-free by using a 1:1 gluten-free flour blend. Additionally, if you or someone you’re serving has allergies, be sure to check for any ingredients that may be of concern—particularly with shredded coconut and maraschino cherries, which can contain sulfites.

Pineapple Upside Sugar Cookies

Indulge in Pineapple Upside Sugar Cookies That Wow!

These Pineapple Upside Sugar Cookies are a delightful twist on a classic, offering vibrant tropical flavors in a soft, chewy cookie.
Print Recipe Pin Recipe
Prep Time 15 minutes mins
Cook Time 15 minutes mins
Total Time 30 minutes mins
Servings: 24 cookies
Course: Dessert
Cuisine: Tropical
Calories: 150
Ingredients Equipment Method Nutrition Notes

Ingredients
  

For the Cookie Dough
  • 1 cup Unsalted Butter at room temperature
  • 1 cup Granulated Sugar
  • 1 large Large Egg
  • 2 teaspoons Vanilla Extract
  • 2 cups All-Purpose Flour can swap for gluten-free
  • 1 teaspoon Baking Powder
  • ½ teaspoon Salt
For the Tropical Twist
  • 1 cup Crushed Pineapple drained well
  • ½ cup Brown Sugar
  • ½ cup Shredded Coconut optional
For Optional Toppings
  • 12 pieces Maraschino Cherries optional

Equipment

  • mixing bowl
  • Baking Sheets
  • Parchment Paper
  • spatula
  • whisk
  • Measuring Spoons
  • Spoon

Method
 

Step-by-Step Instructions
  1. Preheat your oven to 350°F (175°C). Line your baking sheets with parchment paper.
  2. In a mixing bowl, beat the softened unsalted butter and granulated sugar on medium speed for 2 to 3 minutes until light and fluffy.
  3. Add a large egg and vanilla extract, beating on low speed until well combined.
  4. In a separate bowl, whisk together flour, baking powder, and salt until evenly mixed.
  5. Gradually add the dry ingredients to the wet mixture, stirring gently until just combined.
  6. Fold in the drained crushed pineapple and shredded coconut until evenly distributed.
  7. Mix together brown sugar with 1 to 2 teaspoons of flour in a small bowl.
  8. Scoop portions of cookie dough and roll in brown sugar mixture until coated.
  9. Place coated dough balls on baking sheets, spaced about 2 inches apart, and lightly flatten each ball.
  10. Press a maraschino cherry into the center of each cookie, if desired.
  11. Bake for 12 to 15 minutes, until the edges are golden brown.
  12. Cool on baking sheets for 5 minutes before transferring to a wire rack to cool completely.

Nutrition

Serving: 1cookieCalories: 150kcalCarbohydrates: 20gProtein: 1gFat: 7gSaturated Fat: 4gPolyunsaturated Fat: 0.5gMonounsaturated Fat: 2gCholesterol: 30mgSodium: 100mgPotassium: 40mgFiber: 0.5gSugar: 10gVitamin A: 200IUCalcium: 10mgIron: 0.5mg

Notes

Drain pineapple well to avoid soggy dough. Chill the dough if it's too soft. Customize toppings to your preference.

Tried this recipe?

Let us know how it was!

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Welcome, Fellow Food Adventurer!

Hi, I'm Julie! I'm a passionate home cook who believes every meal should be an adventure. Join me as I share tested recipes, kitchen stories, and culinary discoveries that will inspire your next delicious creation.

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