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Home » Irresistibly Easy Pineapple Upside Down Sugar Cookies Recipe

Irresistibly Easy Pineapple Upside Down Sugar Cookies Recipe

February 8, 2026 by NatalieDessert

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There’s something wonderfully nostalgic about the combination of sugar cookies and a fruity twist, and that’s exactly what these Pineapple Upside Down Sugar Cookies deliver. Picture a sunny afternoon where the sweet aroma of buttery cookies fills your kitchen, instantly transporting you to a tropical paradise. This delightful recipe is perfect for anyone eager to put a fun twist on classic treats, whether you’re hosting a gathering or simply satisfying your own sweet cravings.

I remember the first time I tried these cookies; they instantly became a hit among friends for their chewy texture and the juicy, caramelized pineapple topping that adds a pop of flavor. With minimal effort required, even beginner bakers can impress guests with this vibrant twist on a beloved classic. Get ready to indulge in an easy, crowd-pleasing dessert that not only looks stunning but also brings a joyful taste of the tropics straight to your plate!

Why are Pineapple Upside Down Sugar Cookies so special?

Uniquely Flavorful: The juicy pineapple topping paired with buttery sugar cookies creates a tropical explosion of taste.

Beginner-Friendly: This recipe is perfect for novice bakers, requiring minimal ingredients and easy steps to achieve success.

Visually Stunning: Each cookie resembles a mini upside-down cake, making them a show-stopping treat for gatherings.

Versatile Option: Plus, you can easily switch up the toppings or mix-ins, like nuts or toasted coconut, for a personal touch.

Quick and Effortless: Bake them in just 12-14 minutes, saving valuable time for busy schedules.

Enjoy these cookies alongside a refreshing iced chai or as a delightful pairing with grilled kabobs during your next get-together!

Pineapple Upside Down Sugar Cookies Ingredients

For the Cookie Batter

  • Unsalted Butter – Provides richness and moisture; use softened for easy mixing.
  • Granulated Sugar – Sweetens and aids in browning; reduce by 2-3 tablespoons for a lighter touch.
  • Egg – Binds ingredients and contributes to texture; make sure it’s at room temperature for better incorporation.
  • Vanilla Extract – Adds depth to flavor; opt for pure vanilla for the best taste.
  • All-Purpose Flour – Forms the cookie structure; for gluten-free, use a 1:1 baking blend.
  • Baking Soda – Acts as a leavening agent, ensuring lightness in your cookies.
  • Salt – Enhances flavors; it’s essential even in sweet recipes.

For the Topping

  • Canned Pineapple Rings – A juicy topping that adds sweetness; ensure they are well-drained and patted dry for best results.
  • Additional Sugar for Sprinkling – Adds a sweet finish to your Pineapple Upside Down Sugar Cookies.

Get ready to create a delightful dessert that will make you fondly reminisce about sunny days and sweet treats!

How to Make Pineapple Upside Down Sugar Cookies

  1. Preheat the Oven: Begin by preheating your oven to 350°F (175°C). This ensures your cookies bake evenly and become perfectly golden brown.
  2. Cream the Butter and Sugar: In a large mixing bowl, combine softened unsalted butter and granulated sugar. Beat them together until the mixture is light and fluffy, about 2-3 minutes.
  3. Incorporate Egg and Vanilla: Add in one room-temperature egg and a splash of pure vanilla extract. Mix until fully blended, as this will enhance the cookies’ flavor.
  4. Mix Dry Ingredients: In a separate bowl, whisk together all-purpose flour, baking soda, and salt. Gradually fold this dry mixture into the wet ingredients, creating a soft dough.
  5. Shape the Cookies: Roll the dough into 1½ tablespoon-sized balls and slightly flatten them. Place them on a lined baking sheet.
  6. Add Toppings: Gently press a well-drained pineapple ring onto each cookie, and sprinkle with a little extra sugar to add sweetness and enhance browning during baking.
  7. Bake: Slide your tray into the preheated oven and bake for 12-14 minutes. Look for edges that are golden and set but the centers should remain soft.
  8. Cool the Cookies: Allow the cookies to cool on the baking sheet for about 5 minutes before transferring them to a wire rack to cool completely.

Optional: Top with a maraschino cherry for a delightful finishing touch!

Exact quantities are listed in the recipe card below.

Storage Tips for Pineapple Upside Down Sugar Cookies

Room Temperature: Store cookies in an airtight container at room temperature for up to 7 days to maintain freshness and chewiness.

Fridge: If you prefer, these cookies can also be kept in the fridge; they will stay good for up to 10 days. Just ensure they’re in an airtight container to prevent them from drying out.

Freezer: For long-term storage, freeze cookies in layers separated by parchment paper. They can be kept for up to 3 months. Thaw at room temperature before serving for the best taste.

Reheating: If you desire a warm treat, gently reheat cookies in the microwave for about 10-15 seconds—this brings back their chewy goodness!

Pineapple Upside Down Sugar Cookies Variations

Feel free to let your creativity shine and customize these cookies to match your taste preferences and dietary needs!

  • Fresh Pineapple: Swap canned pineapple for thinly sliced, well-drained fresh pineapple for a brighter flavor.
  • Coconut Whisper: Lightly dust the cookies with toasted coconut before baking for a tropical aroma and extra crunch.
  • Nutty Delight: Mix in chopped walnuts or macadamia nuts into the dough for added texture and a nutty richness.
  • Chocolatey Twist: Add a handful of semi-sweet or dark chocolate chips to the batter for a decadent chocolate-pineapple fusion.
  • Spicy Kick: Sprinkle a pinch of cinnamon or nutmeg into the batter for a warm spice note that contrasts beautifully with the pineapple.
  • Zesty Citrus: Incorporate a teaspoon of lemon or orange zest into the dough for a refreshing citrus twist that brightens the overall flavor.
  • Gluten-Free Magic: Use a 1:1 gluten-free baking blend in place of all-purpose flour to make these cookies suitable for gluten-sensitive friends.
  • Cherry On Top: For a classic touch, consider adding a maraschino cherry atop the pineapple before baking, creating a visually stunning treat.

With these variations, you can tailor your Pineapple Upside Down Sugar Cookies to fit every occasion and every palate!

Tips for the Best Pineapple Upside Down Sugar Cookies

  • Pineapple Prep: Ensure your canned pineapple rings are well-drained and patted dry to avoid excess moisture, which can affect cookie texture.
  • Perfect Mixing: Cream your butter and sugar until light and fluffy; this is crucial for creating a soft and chewy texture in your pineapple cookies.
  • Room Temperature Ingredients: Use room-temperature egg and butter for smoother batter integration and better cookie rise.
  • Don’t Overbake: Keep an eye on your cookies; bake just until the edges turn golden for the best soft texture.
  • Topping Variations: Experiment with toppings like toasted coconut or nuts; they add flavor and a fun twist to your delicious pineapple upside down sugar cookies.

What to Serve with Pineapple Upside Down Sugar Cookies?

Elevate your cookie experience with delightful pairings that bring out the tropical flavors of these charming treats.

  • Iced Chai Latte: The creamy spice of iced chai complements the sweet cookies beautifully, offering a refreshing balance and cozy warmth.
  • Pineapple Iced Tea: Keep the pineapple theme alive! This fruity drink enhances the tropical vibe and adds a zesty twist to your dessert.
  • Grilled Chicken Skewers: The savory, smokey taste of grilled kabobs creates a delightful contrast, making for an exciting sweet and savory pairing.
  • Tropical Fruit Salad: A fresh medley of mango, kiwi, and berries not only brightens your plate but also adds texture and cheeky sweetness.
  • Coconut Whipped Cream: Serve a dollop on the side; its subtle richness mirrors the cookies while delivering an extra creamy bite for indulgence.
  • Chocolate Dipping Sauce: For a fun twist, take it up a notch by drizzling or dunking cookies in a warm chocolate sauce—an irresistible treat!
  • Vanilla Ice Cream: Creamy vanilla ice cream melts perfectly over warm cookies, making for a nostalgic and refreshing dessert option that’s a crowd-pleaser.
  • Honey Citrus Glaze: Drizzle over the cookies for a touch of citrus brightness, highlighting the pineapple’s flavor while adding a lovely sheen.

Embrace the joy of sharing these cookies with fun pairings that elevate your gathering and create lasting memories!

Pineapple Upside Down Sugar Cookies Recipe FAQs

What is the best way to select ripe pineapple for the cookies?
Choose a ripe pineapple by looking for one that has a sweet fragrance and gives slightly when pressed. The skin should be golden with minimal green. For this recipe, if using canned pineapple, ensure it is well-drained and patted dry to avoid excess moisture in your cookies. Fresh pineapple can be thinly sliced and blotted dry for the best results.

How should I store leftover Pineapple Upside Down Sugar Cookies?
Store your cookies in an airtight container at room temperature for up to 7 days to keep them fresh and chewy. If you prefer them chilled, refrigeration is also an option—just make sure they’re in an airtight container to prevent them from drying out. For longer storage, freeze cookies in layers separated by parchment paper, and they can be kept for up to 3 months.

Can I freeze Pineapple Upside Down Sugar Cookies? How?
Absolutely! To freeze your Pineapple Upside Down Sugar Cookies, first, ensure they are completely cool. Place them in a single layer on a baking sheet and freeze for about 1-2 hours. Once frozen, transfer the cookies into an airtight container or a freezer bag, layering them with parchment paper to prevent sticking. Thaw at room temperature when you’re ready to enjoy them—this keeps their lovely texture intact.

What if my cookies spread too much while baking?
If your cookies spread too much, it might be due to overly soft butter or insufficient chilling time. Make sure your butter is softened to room temperature but not melted. For better control, consider chilling the dough for about 30 minutes before shaping and baking. Also, ensure you’re measuring your flour correctly, as too little flour can also cause spreading.

Are there any dietary considerations for Pineapple Upside Down Sugar Cookies?
These cookies can be made gluten-free by swapping all-purpose flour for a 1:1 baking blend. Always check ingredient labels for hidden allergens. As for pets, avoid sharing these cookies with dogs and cats, as sugar and certain toppings (like pineapple) can upset their stomach.

Can I substitute other fruits for the pineapple?
Certainly! You can try using peaches, mandarin oranges, or cherries instead. Just make sure to drain and pat them dry, similar to how you would with the pineapple. This allows for delightful variations that suit your taste preferences!

Pineapple Upside Down Sugar Cookies

Irresistibly Easy Pineapple Upside Down Sugar Cookies Recipe

These Pineapple Upside Down Sugar Cookies combine classic sugar cookie charm with a fruity tropical twist, making them a delightful treat.
Print Recipe Pin Recipe
Prep Time 15 minutes mins
Cook Time 14 minutes mins
Cooling Time 5 minutes mins
Total Time 34 minutes mins
Course Dessert
Cuisine American
Servings 24 cookies
Calories 150 kcal

Equipment

  • Mixing bowl
  • Baking sheet
  • Oven

Ingredients
  

For the Cookie Batter

  • 1 cup Unsalted Butter softened
  • 1 cup Granulated Sugar reduce by 2-3 tablespoons for a lighter touch
  • 1 large Egg room temperature
  • 1 teaspoon Vanilla Extract use pure for best taste
  • 2 cups All-Purpose Flour or 1:1 gluten-free blend
  • 1 teaspoon Baking Soda
  • 1/2 teaspoon Salt

For the Topping

  • 1 can Canned Pineapple Rings well-drained and patted dry
  • 2 tablespoons Additional Sugar for Sprinkling

Instructions
 

How to Make Pineapple Upside Down Sugar Cookies

  • Preheat your oven to 350°F (175°C).
  • In a large mixing bowl, combine softened unsalted butter and granulated sugar. Beat until light and fluffy, about 2-3 minutes.
  • Add in one room-temperature egg and vanilla extract. Mix until fully blended.
  • In a separate bowl, whisk together flour, baking soda, and salt. Gradually fold this dry mixture into the wet ingredients.
  • Roll the dough into 1½ tablespoon-sized balls and slightly flatten them on a lined baking sheet.
  • Press a well-drained pineapple ring onto each cookie and sprinkle with a little extra sugar.
  • Bake for 12-14 minutes until edges are golden but centers remain soft.
  • Allow the cookies to cool on the baking sheet for about 5 minutes before transferring to a wire rack.

Notes

Optional: Top with a maraschino cherry for a delightful finishing touch. Experiment with toppings for a fun twist.
Keyword cookies, Dessert, easy baking, Pineapple Upside Down Sugar Cookies, sweets, tropical
Pineapple Upside Down Sugar Cookies
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