Pineapple Upside Down Sugar Cookies That Delight Every Bite

February 24, 2026

By Emma Waters

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Pineapple Upside Down Sugar Cookies That Delight Every Bite

There’s something magical about a warm cookie that just pulls you in, inviting you to take a bite. The sweet aroma of buttery dough mingled with tropical pineapple conjures up memories of sun-drenched summer days and picnics by the beach. These Pineapple Upside Down Sugar Cookies that Delight Every Bite are not just cookies; they are a comforting slice of nostalgia, perfect for cozy gatherings with loved ones. Whether you’re whipping them up for a casual afternoon treat or sharing them at your next family get-together, these cookies are sure to bring smiles all around! This is one you’ll definitely want to pin for later!

Why You’ll Love This Recipe

  • Quick and Easy: Perfect for busy weeknights and last-minute cravings.
  • Tropical Twist: The delightful combination of pineapple brings a unique flavor that’s refreshing and exciting.
  • Crowd-Pleasing: These cookies are guaranteed to impress friends and family.
  • Adaptable: Easily modify with your favorite mix-ins to add a personal touch.
  • Perfect for Any Occasion: They’re great for holidays, birthdays, or just because—a delightful treat any day!

What You’ll Need

Gather These Simple Ingredients

  • 1 cup unsalted butter (softened)
  • 1 cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract (optional)
  • 2 cups all-purpose flour (or gluten-free blend)
  • 1 teaspoon baking soda
  • 1/2 teaspoon salt
  • 1 can canned pineapple rings (well-drained)
  • 2 tablespoons additional sugar for sprinkling

How to Make Pineapple Upside Down Sugar Cookies That Delight Every Bite

Let’s Make It Together

  1. Start by preheating your oven to 350°F (175°C) and lining a baking sheet with parchment paper. This cozy little step helps prevent those buttery cookies from sticking!

  2. In a large mixing bowl, cream together the softened butter and granulated sugar until it’s light and fluffy—a delightful mixture that should look like sunshine in a bowl.

  3. Add the egg and vanilla extract (if using) to the butter mixture, mixing until well combined. The aroma of vanilla really elevates the comfort level of this recipe!

  4. In another bowl, whisk together the all-purpose flour (or gluten-free blend), baking soda, and salt. Gradually incorporate this dry mixture into the wet ingredients, stirring just until the dough comes together.

  5. Now for the fun part! Using a tablespoon, scoop the dough and place it on your prepared baking sheet. Make sure to leave space between each scoop—these cookies love to spread out and become friends in the oven.

  6. Once all the dough is scooped, it’s time to arrange your well-drained pineapple rings on top of each cookie. Don’t be shy; each cookie deserves a slice of that juicy goodness!

  7. Sprinkle a pinch of the additional sugar over the top of each pineapple ring. This little sprinkle creates a delightful, caramelized crust as they bake.

  8. Bake in your preheated oven for 10-12 minutes until the edges are golden and the cookies are puffed and tender. Allow them to cool on the baking sheet for a few minutes before transferring them to a wire rack to cool completely.

  9. Finally, take a moment to savor that heavenly scent while the cookies cool; it’s like a warm hug for your kitchen!

Variations & Creative Twists

Delicious Variations to Try

  • Coconut Tinged: Add shredded coconut to the dough for a tropical encounter with each bite.
  • Zesty Citrus: Mix in some lemon or orange zest to enhance that fruity flavor, giving your cookies a refreshing zing.
  • Choco-Pineapple Fusion: Introduce chocolate chips to the dough because who doesn’t love the pairing of chocolate and pineapple?
  • Nutty Delight: Fold in some finely chopped pecans or walnuts for added crunch and richness.

Chef Emma’s Helpful Tips

  • Make-Ahead: The dough can be made ahead of time and stored in the refrigerator for up to 3 days. Simply scoop and bake when you’re ready for warm cookies!
  • Ingredient Swaps: If you prefer a different flavor, you can substitute the pineapple with peaches or cherries.
  • Storing Leftovers: Keep any leftover cookies in an airtight container at room temperature for up to 5 days—it’s a challenge, but they’ll stay fresh and delicious!
  • Slicing Tricks: For neat cookie rounds, chill the dough for 30 minutes before scooping into balls; this will prevent too much spreading.

Nutrition Information per Serving

  • Serving Size: 1 cookie
  • Calories: 150
  • Carbohydrates: 20g
  • Sugar: 9g
  • Fat: 7g
  • Protein: 1g
  • Sodium: 75mg

Frequently Asked Questions

Reader FAQs About Pineapple Upside Down Sugar Cookies That Delight Every Bite

Can I make this ahead?
Absolutely! You can make the dough ahead of time and store it in the fridge for up to three days before baking.

Can I use different ingredients?
Yes! Feel free to substitute the pineapple with your favorite fruits or even add some chocolate chips for an indulgent twist.

How do I store leftovers?
Store any leftover cookies in an airtight container at room temperature for up to five days—if they last that long!

How long does it last?
These cookies are best enjoyed within five days of baking, but they can be frozen for up to three months for a longer shelf life.

Wrapping It Up

These Pineapple Upside Down Sugar Cookies that Delight Every Bite are not just delightful desserts—they are enveloped in warmth, nostalgia, and the spirit of togetherness. With their tropical twist, they bring a touch of sunshine to any dessert table, making them a memorable treat for every occasion. Save this recipe to your cozy treats board so it’s ready when you need an indulgent pick-me-up! Happy baking, dear friends!

Pineapple Upside Down Sugar Cookies

These delightful cookies pair the sweet richness of buttery dough with the refreshing taste of pineapple, perfect for any occasion.
Prep Time 15 minutes
Cook Time 12 minutes
Total Time 27 minutes
Course Dessert, Snack
Cuisine American, Tropical
Servings 24 cookies
Calories 150 kcal

Ingredients
  

Cookie Base

  • 1 cup unsalted butter (softened)
  • 1 cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract (optional)
  • 2 cups all-purpose flour (or gluten-free blend)
  • 1 teaspoon baking soda
  • 1/2 teaspoon salt

Toppings

  • 1 can canned pineapple rings (well-drained)
  • 2 tablespoons additional sugar for sprinkling

Instructions
 

Preparation

  • Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper.
  • In a large mixing bowl, cream together the softened butter and granulated sugar until light and fluffy.
  • Add the egg and vanilla extract (if using) to the butter mixture and mix until well combined.
  • In another bowl, whisk together the all-purpose flour, baking soda, and salt. Gradually incorporate this dry mixture into the wet ingredients.

Baking

  • Scoop the dough using a tablespoon and place it on the prepared baking sheet, leaving space between each scoop.
  • Arrange the well-drained pineapple rings on top of each cookie and sprinkle with additional sugar.
  • Bake in the preheated oven for 10-12 minutes until edges are golden. Allow cookies to cool on the baking sheet before transferring to a wire rack.

Notes

Dough can be made ahead of time and stored in the refrigerator for up to 3 days. Store any leftover cookies in an airtight container at room temperature for up to 5 days.

Nutrition

Serving: 1gCalories: 150kcalCarbohydrates: 20gProtein: 1gFat: 7gSodium: 75mgSugar: 9g
Keyword Pineapple Cookies, Sugar Cookies, Tropical Desserts
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