Name: Pineapple Upside Sugar Cookies A Fun Tropical Treat Recipe
Prep time: 20 min
Cook time: 12 min
Total time: 32 min
Yield: 12
Cuisine: American
Ingredients: 1 cup (226 grams) unsalted butter, softened; 1 cup (200 grams) granulated sugar; 1 egg; 1 teaspoon vanilla extract; 2 1/2 cups (313 grams) all-purpose flour; 1/2 teaspoon baking powder; 1/4 teaspoon salt; 1/2 cup crushed pineapple, drained; Maraschino cherries, halved; Brown sugar for sprinkling

Sweet pineapple upside sugar cookies bring a burst of sunshine to your dessert plate.

Tropical flavors dance through each delightful bite.

Crisp edges complement a soft, tender center with unexpected fruity notes.

Delicate crumbles melt on your tongue, whisking you to a beachy paradise.

Subtle caramel undertones peek through the bright pineapple essence.

Baking these treats fills your kitchen with an irresistible aroma that promises pure joy.

Christmas Brie Cheese Platter Ingredients

Main Ingredients:

Flour Mixture: .

Flour: Provides the base structure for the cookies.
Baking Powder: Helps the cookies rise and become fluffy.
Salt: Enhances the overall flavor.

Wet Ingredients:

Butter: Adds richness and helps create a soft texture.
Granulated Sugar: Provides sweetness and helps with cookie browning.
Egg: Binds the ingredients and adds moisture.
Vanilla Extract: Adds depth of flavor.

Fruit and Topping Ingredients:

Crushed Pineapple: Brings tropical moisture and fruity flavor.
Maraschino Cherries: Adds a sweet and colorful garnish.
Brown Sugar: Provides extra sweetness and caramel-like notes.

Directions for Pineapple Upside Sugar Cookies

Step 1: Warm Up the Oven

Get your oven ready by heating it to 350°F. Line a baking sheet with parchment paper to prevent sticking and make cleanup a breeze.

Step 2: Create a Creamy Base

In a large mixing bowl, blend butter and sugar until the mixture becomes light and airy. The texture should look fluffy and smooth.

Step 3: Add Moisture and Flavor

Crack an egg into the butter mixture and pour in vanilla extract. Mix thoroughly until everything is well combined and looks smooth.

Step 4: Combine Dry Ingredients

In a separate bowl, whisk together:

All-purpose flour
Baking powder
Salt

Slowly incorporate these dry ingredients into the wet mixture, stirring until a consistent dough forms.

Step 5: Fold in Tropical Goodness

Gently mix in drained crushed pineapple, ensuring it’s evenly distributed throughout the cookie dough.

Step 6: Shape the Cookies

Scoop tablespoon-sized portions of dough onto the prepared baking sheet. Space the cookies about 2 inches apart to allow room for spreading.

Step 7: Add Decorative Touches

Press a halved maraschino cherry into the center of each cookie. Sprinkle a pinch of brown sugar on top for extra sweetness and crunch.

Step 8: Bake to Golden Perfection

Place the baking sheet in the oven and bake for 10-12 minutes. Look for lightly golden edges as a sign of doneness.

Step 9: Cool and Enjoy

Let the cookies rest on the baking sheet for a few minutes. Transfer to a wire rack to cool completely before serving.

Drain Pineapple Thoroughly: Pat crushed pineapple with paper towels to remove excess moisture, preventing soggy cookies.
Chill Dough for Firmness: Refrigerate cookie dough for 30 minutes before baking to prevent spreading and maintain shape.
Swap Cherries Creatively: Replace maraschino cherries with dried cranberries or coconut flakes for different flavor profiles.
Room Temperature Ingredients: Ensure butter and egg are at room temperature for smoother, more evenly mixed cookie dough.
Adjust Sweetness Levels: Reduce brown sugar sprinkle for less sweetness or add a dash of cinnamon for extra warmth.

Store Pineapple Cookies in a Sealed Container

Store cookies in an airtight container with parchment paper between layers for up to 5 days. Keep in the refrigerator to maintain freshness and prevent cherries from spoiling quickly.
Wrap individual cookies tightly in plastic wrap, place in freezer-safe container, and store for 2-3 months. Thaw at room temperature for 30-45 minutes before serving.
Place cookies in sealed container with tight lid, keeping away from direct sunlight and heat. Consume within 3 days for best flavor and texture.
Add small silica gel packet inside storage container to absorb excess moisture and prevent cookies from becoming soggy or soft.

Chocolate Covered Pretzels Match Tips

Tropical Cocktail Companion: Mix a zesty piña colada to complement the sweet-tangy cookie flavors, highlighting the pineapple's tropical essence.
Creamy Coconut Refreshment: Pair with a chilled coconut milk latte, enhancing the cookie's tropical undertones and providing a smooth, rich contrast.
Sparkling Citrus Celebration: Serve alongside a light prosecco or sparkling white wine, whose effervescence cuts through the cookie's sweetness and adds elegance.
Island-Inspired Tea Match: Brew a gentle mango or passion fruit herbal tea, creating a harmonious flavor bridge that echoes the cookie's fruity character.

Brie Cheese Platter Holiday Layouts

Gluten-Free Tropical Cookie: Replace wheat flour with almond or coconut flour for a gluten-free version. Use gluten-free baking powder to ensure total allergen safety.
Vegan Pineapple Delight: Substitute butter with coconut oil and use a flax egg instead of regular egg. Select plant-based maraschino cherries to maintain the classic cookie profile.
Low-Sugar Pineapple Treat: Swap granulated sugar with monk fruit sweetener or stevia. Reduce brown sugar topping and use natural fruit sweetness from fresh pineapple chunks.
Coconut Pineapple Fusion: Add shredded unsweetened coconut to the cookie dough. Replace maraschino cherry with toasted coconut flakes for extra tropical flavor and crunch.

FAQs

Can I use canned pineapple for this recipe?

Yes, you can use canned crushed pineapple. Just make sure to drain it well to prevent excess moisture in the cookies.

How do I know if the cookies are done baking?

Look for lightly golden edges. The cookies should be slightly firm but not hard when you touch them.

Can I substitute the maraschino cherry?

Absolutely! You can use other candied cherries or skip the cherry entirely if you prefer. Some people like to use a slice of fresh pineapple instead.

What makes these cookies different from regular sugar cookies?

The crushed pineapple adds moisture and a tropical flavor that makes these cookies unique and more tender compared to traditional sugar cookies.

Sugar Cookies That Flip Pineapple Upside Down with a Twist

Tropical Twist: Enjoy a delightful flavor journey with these unique cookies that blend sweet pineapple and classic sugar cookie base.
Super Simple Baking: Perfect for bakers of all skill levels, this recipe requires minimal ingredients and basic mixing techniques anyone can master.
Quick Family Dessert: Whip up these crowd-pleasing cookies in less than 30 minutes, making them ideal for spontaneous family treats or last-minute gatherings.
Kid-Friendly Creation: Children will love helping press cherries into cookies and sprinkling brown sugar, turning baking into a fun interactive experience.

Marcus Hale

Founder & Recipe Storyteller

Expertise

Demystifying knife work, sauce emulsification, and pastry basics.
Curating seasonal guides that adapt global recipes to local, in-season produce.
Crafting blog posts, videos, and social media tips.

Education

Holyoke Community College – HCC-MGM Culinary Arts Institute

Program: Culinary Arts Certificate
Focus: Hands-on global cuisine training emphasizes sustainable cooking and recipe development under accredited chefs.

Marcus grew up surrounded by maple trees, farm stands, and the smell of Sunday stew simmering on the stove. After earning his Culinary Arts Certificate from the HCC-MGM Culinary Arts Institute, he knew he didn’t want to work in fancy kitchens, he wanted to cook for real people.

At Whip Up Cook Up, Marcus is the guy turning memories into meals. His recipes are fast, full of flavor, and built for home cooks who want big taste without the drama.

The Perfect Pineapple Upside Sugar Cookies Recipe: A Sunny Tropical Treat