There’s something undeniably delightful about turning a classic dessert into a playful cookie treat. As the sweet, buttery aroma fills your kitchen, memories of beach vacations and summer barbecues flood your senses. Introducing Pineapple Upside Down Sugar Cookies—a charming twist on the beloved pineapple upside-down cake—in cookie form!

Just imagine biting into a soft, chewy cookie with a glorious topping of caramelized pineapple, bursting with tropical sweetness. They’re not only quick to make but also a stunning crowd-pleaser for gatherings or cozy nights in. Best of all, this recipe allows for easy adaptations, including a gluten-free option, so everyone can indulge.

If you’re ready to add some sunshine to your baking routine, let’s dive into this delightful recipe!

Why You’ll Love Pineapple Upside Down Sugar Cookies

Joyful Flavor: Each bite bursts with sweet, tropical delight, making them perfect for summer gatherings or any day that needs a lift.
Chewy Texture: The combination of soft, buttery cookie and chewy caramelized pineapple is irresistibly satisfying.
Quick & Easy: With simple steps, you can whip these cookies up in no time, impressing friends and family effortlessly.
Adapts Beautifully: Feel free to swap the pineapple for other fruits like cherries or strawberries, creating a unique twist each time.
Gluten-Free Option: Enjoy these treats regardless of dietary needs by using a gluten-free flour blend, ensuring everyone can join in the fun.
Crowd-Pleaser: These cookies combine nostalgia and a fun presentation, making them an instant favorite at any event. For another sweet treat, check out the delightful Hot Chocolate Cookies!

Pineapple Upside Down Sugar Cookies Ingredients

For the Cookie Dough

Unsalted Butter – provides rich flavor and helps achieve a tender cookie; substitute with margarine or coconut oil for dairy-free options.
Granulated Sugar – adds sweetness and assists in creating a crisp edge; can be reduced slightly for a less sweet cookie.
Large Egg – binds the ingredients together, contributing to texture; use a flaxseed egg for a vegan version.
Vanilla Extract (optional) – enhances flavor beautifully; you can replace it with almond extract for a different profile.
All-Purpose Flour or Gluten-Free Blend – forms the dough structure; use a gluten-free blend for gluten-sensitive diets.
Baking Soda – acts as a leavening agent for light cookies; no substitutes—essential for the right texture.
Salt – balances sweetness and enhances flavor; it’s crucial for overall taste.

For the Topping

Canned Pineapple Rings – adds tartness and moisture; be sure to drain well to avoid excess liquid. Fresh pineapple can also be used for added texture.
Additional Sugar (for sprinkling) – enhances caramelization on the fruit topping and adds that extra sweetness.

With these ingredients, you’re on your way to creating delectable Pineapple Upside Down Sugar Cookies that will charm everyone at your table!

How to Make Pineapple Upside Down Sugar Cookies

Preheat the oven to 350°F (180°C) and line your baking trays with parchment paper. This sets the stage for perfect baking and prevents sticking.
Cream softened butter and granulated sugar together until light and fluffy, about 2-3 minutes. This step creates a rich texture that will bring your cookies to life.
Beat in the large egg and optional vanilla extract until everything is well combined. The mixture should be creamy and smooth.
Whisk together the all-purpose flour (or gluten-free blend), baking soda, and salt in a separate bowl. Gradually combine this dry mixture with the wet ingredients to form a soft dough.
Scoop 2 tablespoons of dough for each cookie onto the prepared trays, ensuring there’s space in between them. This allows for spreading as they bake.
Press a pineapple ring gently into the center of each cookie dough mound. Sprinkle a bit of sugar on top to enhance the caramelization during baking.
Bake for 11-13 minutes until the edges are golden brown and the centers are set. Let them cool slightly on the tray before transferring them to a wire rack to cool completely.

Optional: Drizzle with chocolate or caramel sauce for an extra touch of indulgence.

Exact quantities are listed in the recipe card below.

What to Serve with Pineapple Upside Down Sugar Cookies?

Imagine indulging in your cookies as you create a bright, tropical-themed dessert experience. These treats radiate joy, so let’s complement them with delicious pairings!

Vanilla Bean Ice Cream: A scoop of creamy vanilla ice cream beautifully balances the sweetness and adds a cooling contrast to warm cookies.
Tropical Fruit Salad: A refreshing mix of mango, kiwi, and strawberries enhances the tropical vibe while providing a light, fresh crunch.
Coconut Whipped Cream: Light and fluffy, this dairy-free topping adds a tropical twist that harmonizes perfectly with the pineapple flavors.
Iced Herbal Tea: A glass of refreshing herbal tea, flavored with mint or pineapple, complements the cookies without overpowering their sweetness.
Lemonade Spritzers: The zesty tang of lemonade adds a delightful sparkle, cutting through the richness and making each bite even more enjoyable.
Chocolate Drizzle: A quick drizzle of melted chocolate over the cookies enhances the flavor while adding a touch of elegance to your presentation.
Mango Sorbet: This dairy-free dessert offers a fruity refreshment that perfectly pairs with the rich flavors of the cookies.
Pineapple Coconut Smoothie: A delicious smoothie with pineapple, coconut milk, and a hint of lime enhances the tropical theme while being a delightful companion.
Banana Bread Pudding: For a cozy twist, serve warm banana bread pudding alongside the cookies to bring a comforting and indulgent touch.

Variations & Substitutions for Pineapple Upside Down Sugar Cookies

Feel free to get creative and customize these delightful cookies to fit your taste!

Gluten-Free: Use a 1:1 gluten-free flour blend to cater to gluten-sensitive diets without sacrificing taste or texture.
Dairy-Free: Substitute unsalted butter with coconut oil or dairy-free margarine for a completely dairy-free cookie.
Fruity Twist: Try using fresh cherries, peaches, or strawberries on top for a pop of color and a different flavor experience. The bright hues bring a special charm to the cookie presentation!
Spiced Up: Add a pinch of cinnamon or nutmeg to the dough for a warm, cozy flavor that complements the sweetness of the pineapple perfectly.
Nutty Addition: Fold in some chopped walnuts or pecans into the cookie dough for an added crunch and depth of flavor. The texture contrast is delightful!
Sugar Level Adjustments: Reduce the granulated sugar slightly for a less sweet cookie or even substitute with coconut sugar for a caramel-like flavor.
Tropical Fusion: Incorporate shredded coconut into the dough to enhance the tropical feel of your Pineapple Upside Down Sugar Cookies. It’s like a beach vacation in every bite!
Extra Sweetness: Drizzle with caramel or chocolate sauce after baking for a decadent touch that transforms these cookies into a true indulgence. The drizzle will elevate your cookie experience to gourmet levels!

How to Store and Freeze Pineapple Upside Down Sugar Cookies

Room Temperature: Store cookies in an airtight container at room temperature for up to 3 days to maintain freshness and flavor.

Fridge: For slightly longer storage, refrigerate your cookies in a sealed container for about 5-7 days, ensuring they’re protected from moisture.

Freezer: Freeze Pineapple Upside Down Sugar Cookies in a single layer in an airtight container for up to 2 months. Thaw at room temperature before serving or reheat in a low oven for a warm treat.

Reheating: To enjoy cookies warm, place them in a preheated oven at 300°F (150°C) for about 5-7 minutes until slightly warmed through.

Expert Tips for Pineapple Upside Down Sugar Cookies

Chill the Dough: If your cookies spread too much during baking, chilling the dough for 20 minutes can help maintain their shape and texture.
Use Softened Butter: Always ensure your butter is softened, not melted, to achieve the desired fluffy consistency and tender cookie.
Drain Pineapple Well: Make sure to drain the canned pineapple rings thoroughly to prevent excess moisture from affecting the cookie’s texture.
Add Variation: Explore different fruits for the topping, such as cherries or peaches, to give each batch of Pineapple Upside Down Sugar Cookies a unique twist.
Sugar Sprinkling: Don’t skip the extra sprinkle of sugar on the pineapple; it enhances caramelization and adds a delightful crispness.
Storage Tip: Keep cookies fresh by adding a slice of bread to the storage container; it absorbs moisture and prolongs their deliciousness.

Pineapple Upside Down Sugar Cookies Recipe FAQs

How do I choose the best pineapple for this recipe?
Absolutely! For the best flavor and texture in your Pineapple Upside Down Sugar Cookies, choose fresh pineapple that is ripe, fragrant, and free of dark spots or blemishes. If using canned pineapple, opt for rings packed in juice rather than syrup to avoid extra sweetness; just be sure to drain them well before use to prevent excess moisture in your cookies.

What’s the best way to store leftover cookies?
Store your cookies at room temperature in an airtight container for up to 3 days. To keep them even fresher longer, try placing a slice of bread inside the container; it works wonders at absorbing moisture and keeping your cookies soft! If you need to store them longer, move to the freezer to preserve their deliciousness.

Can I freeze Pineapple Upside Down Sugar Cookies?
Yes, you can! To freeze, lay your cookies in a single layer on a baking sheet until firm, then transfer them to an airtight container or a resealable freezer bag with parchment paper in between layers. They’ll stay fresh for up to 2 months. When ready to enjoy, simply thaw at room temperature or reheat them in a low oven at 300°F (150°C) for about 5-7 minutes.

What should I do if my cookies spread too much while baking?
Very often, cookie spreading can happen if the dough is too warm. A simple fix is to chill the dough for about 20 minutes before baking. This helps solidify the fats in the dough, preserving their shape as they bake. If they’re still spreading, make sure your butter is softened (not melted) next time, which is critical for achieving the right texture.

Are there any allergy considerations for this recipe?
Certainly! For those with gluten sensitivity, you can use a gluten-free flour blend as mentioned in the ingredients. Also, if you’re dealing with dairy allergies, substitute the unsalted butter with margarine or coconut oil. Lastly, remember that the egg can be replaced with a flaxseed egg (1 tablespoon ground flaxseed mixed with 2.5 tablespoons water, let sit for 5 minutes) for a vegan option. It’s always best to read the labels of all your ingredients!

Can I use fresh pineapple instead of canned?
Absolutely! Fresh pineapple can add a more vibrant flavor and unique texture to your cookies. Just make sure to peel, core, and slice the pineapple into rings. For best results, you may want to grill or lightly cook the fresh rings to start caramelizing the sugars before adding them to your cookie dough, which will enhance their sweetness and richness.