Name: Pineapple Upside Down Sugar Cookies: A Tropical Delight!
Prep time: 10 min
Cook time: 13 min
Total time: 30 min
Ingredients: 1 cup Unsalted Butter (softened); 1 cup Granulated Sugar; 1 large Egg (can substitute with a chia egg for a vegan option); 1 teaspoon Vanilla Extract (can substitute with almond extract); 2 cups All-Purpose Flour (can use gluten-free blend); 1 teaspoon Baking Soda (ensure fresh); 1 teaspoon Salt; 1 can Canned Pineapple Rings (or fresh pineapple, dried well); 1 tablespoon Additional Sugar for Sprinkling (optional)

As I stood in my kitchen, the sweet, tropical aroma of baking cookies wafted through the air, instantly transporting me to sun-kissed beaches. These Pineapple Upside Down Sugar Cookies are a delightful twist on the classic dessert, perfect for those who crave a taste of summer any time of the year. With just a handful of easy-to-find ingredients, this recipe lets you whip up a batch in 30 minutes, making it an ideal choice for families and spontaneous gatherings. The chewy texture combined with the caramelized pineapple creates not only a delicious treat but also a stunning centerpiece that will enchant your loved ones. Ready to add a tropical flair to your cookie repertoire? Let’s dive into how to make these sweet delights!

Why Choose Pineapple Upside Down Cookies?

Tropical Twist: These cookies are a fun, fruity reimagining of the classic pineapple upside-down cake that brings sunshine to any occasion.
Quick to Make: Ready in just 30 minutes, they’re perfect for last-minute dessert cravings or unexpected guests.
Family-Friendly: Kids and adults alike adore the sweet, juicy pineapple atop a soft, chewy cookie.
Versatile Options: Try adding nuts or using fresh pineapple for a personal touch. Looking for more tropical-inspired treats? Check out my Brown Sugar Pineapple Chicken for a delicious meal idea!
Crowd-Pleasing: They’re sure to impress at gatherings, turning heads and satisfying sweet tooth cravings.
Easy Prep: With simple ingredients and straightforward steps, baking becomes a joy, not a chore!
Ready to bring the beach vibes home? Let’s get baking!

Pineapple Upside Down Sugar Cookies Ingredients

• Discover the joyful flavors of Pineapple Upside Down Sugar Cookies with these simple ingredients.

For the Cookies

Unsalted Butter – Adds richness and moisture; use softened butter for the best texture.
Granulated Sugar – Sweetens the cookies and helps achieve a crispy exterior; no substitutes advised.
Large Egg – Binds the ingredients and adds moisture; can substitute with a chia egg for a vegan option.
Vanilla Extract – Enhances flavor depth; substitute with almond extract for a different flavor profile.
All-Purpose Flour – Provides structure; gluten-free flour blend can be used as a substitute.
Baking Soda – Leavening agent for rising; ensure it’s fresh for best results.
Salt – Balances sweetness and enhances flavor; essential for overall taste.

For the Topping

Canned Pineapple Rings – Provides the signature tropical flavor; fresh pineapple can be used if dried well.
Additional Sugar for Sprinkling – Creates a caramelized top; optional but recommended for texture.

Step‑by‑Step Instructions for Pineapple Upside Down Sugar Cookies

Step 1: Preheat Oven
Begin by preheating your oven to 350°F (180°C). While the oven warms, prepare your baking trays by lining them with parchment paper. This will prevent the cookies from sticking and make clean-up a breeze. Make sure to have all your ingredients ready to create delightful Pineapple Upside Down Sugar Cookies!

Step 2: Cream Butter and Sugar
In a mixing bowl, beat together the softened unsalted butter and granulated sugar until the mixture is light and fluffy, which should take about 2-3 minutes. A hand mixer or stand mixer works wonderfully for this! The fluffy texture indicates it’s ready, setting a solid foundation for your cookie dough.

Step 3: Mix in Egg and Vanilla
Add the large egg and vanilla extract to the butter and sugar mixture, then mix until fully incorporated. The batter should appear smooth and glossy, bringing out the tropical notes in your Pineapple Upside Down Sugar Cookies. Ensure everything is combined well for a consistent dough.

Step 4: Combine Dry Ingredients
In a separate bowl, whisk together the all-purpose flour, baking soda, and salt. Gradually add this dry mixture to the wet ingredients, mixing just until a soft dough forms. Be careful not to over-mix; a gentle fold will help keep your cookies tender and delicious.

Step 5: Shape Cookies
Using a cookie scoop or tablespoon, measure about 2 tablespoons of dough for each cookie. Place them on the prepared baking tray, leaving about 2 inches of space between each mound to allow for spreading. This will help ensure your Pineapple Upside Down Sugar Cookies bake evenly and maintain their shape.

Step 6: Top with Pineapple
Take dried pineapple rings and gently press one onto each mound of cookie dough, flattening it slightly to establish a connection. This step not only adds fruity flavor but also makes your cookies visually appealing. Ensure the pineapple is centered for a beautiful presentation.

Step 7: Sprinkle Sugar
Sprinkle a small amount of granulated sugar over each pineapple ring. This sugar will caramelize during baking, giving the cookies a delightful crunchy topping while enhancing the sweetness of the fresh fruit. It’s a simple touch that makes your cookies extra special!

Step 8: Bake
Place the baking tray in the oven and bake for 11-13 minutes. Keep an eye on the cookies; they should be golden around the edges and set in the center. The aroma of the baking Pineapple Upside Down Sugar Cookies will fill your kitchen, creating a cozy and inviting atmosphere.

Step 9: Cooling
Once baked, remove the tray from the oven and allow the cookies to cool on the tray for about 5 minutes. This helps them firm up before transferring them to a wire rack. Once on the rack, let them cool completely to achieve the perfect texture before indulging in these delightful treats.

Make Ahead Options

These Pineapple Upside Down Sugar Cookies are fantastic for meal prep! You can prepare the cookie dough up to 3 days in advance and refrigerate it. Simply mix the ingredients, shape the dough into balls, and store them in an airtight container. The pineapple rings can also be prepped 24 hours ahead—slice fresh pineapple or use canned rings and keep them covered in the fridge to prevent browning. When ready to bake, just place the dough mounds on a baking tray, top with pineapple, and sprinkle sugar before baking. They’ll be just as delicious, saving you precious time on busy days!

What to Serve with Pineapple Upside Down Sugar Cookies

These delightful, tropical cookies deserve accompaniments that highlight their cheerful flavors and textures, creating a truly memorable dessert experience.

Vanilla Bean Ice Cream: A scoop of creamy vanilla ice cream perfectly balances the fruity sweetness, adding a delightful contrast of warm and cold.
Coconut Milk Latte: The rich, nutty flavor of coconut coffee complements the tropical vibes of the cookies, enhancing the overall experience.
Whipped Cream: A fluffy crown of whipped cream adds an airy lightness, making each bite feel indulgently decadent without weighing you down.
Tropical Fruit Salad: Serve alongside a refreshing mix of melons, kiwi, and mango for an explosion of tropical flavors that mirror the cookies.
Pineapple Juice: A chilled glass pairs beautifully, echoing the fruity theme while refreshing your palate between bites.
Chilled Herbal Tea: Mint or hibiscus tea offers a light, fragrant touch that cools the palate and enhances the tropical flair.
Almond Biscotti: For a crunchy texture contrast, consider pairing with these nutty cookies, perfect for dipping into a cup of coffee.
Chocolate Dipped Strawberries: Indulge in rich chocolate and sweet strawberries that complement the vibrant pineapple without overshadowing it.
Maraschino Cherries: Place one on top of each cookie for an added pop of color and flavor, evoking the classic upside-down cake aesthetic.
Rum Cake: For a decadent finish, a slice of rum cake brings a wonderful boozy kick that pairs harmoniously with the sweet, tropical notes of the cookies.

Variations & Substitutions for Pineapple Upside Down Sugar Cookies

Feel free to tailor these delightful cookies to your taste and pantry on hand with a few simple swaps and twists!

Fresh Pineapple: Use thin slices of fresh pineapple instead of canned for a vibrant, juicy topping. Be sure to dry the slices well to maintain the cookie’s texture!
Nutty Addition: Stir in ½ cup of chopped macadamia nuts or pecans to the dough for a delightful crunch that complements the tropical flavor beautifully.
Coconut Twist: Mix in 1 cup of shredded coconut with the dough to create a taste of the tropics; the flavor and texture will make these cookies unforgettable!
Vegan Option: Swap the egg for a chia egg (1 tablespoon chia seeds soaked in 2.5 tablespoons water) and use vegan butter for a delightful vegan treat.
Almond Extract: Replace vanilla extract with almond extract for a unique nutty flavor that pairs wonderfully with pineapple.
Spice it Up: Add a touch of ground cinnamon or nutmeg for a warm and cozy undercurrent that enhances the overall flavor profile.
Tropical Spirit: Top cookies with a maraschino cherry alongside the pineapple ring for that iconic pineapple upside-down cake experience.

Don’t forget to pair your cookies with a scoop of vanilla bean ice cream or whipped cream for a truly decadent dessert experience! If you’re looking for more tropical inspirations, check out my Brown Sugar Pineapple Chicken or indulge in Apple Fritter Cookies for a twist on fruity desserts!

Expert Tips for Pineapple Upside Down Sugar Cookies

Butter Temperature: Ensure butter is softened but not melted; too soft can lead to cookies spreading too much during baking.
Chill Dough: If your kitchen is warm, chill the dough for about 20 minutes to prevent excessive spreading of your Pineapple Upside Down Sugar Cookies.
Parchment Paper: Using parchment paper eliminates the need for greasing the tray, making for easier cookie removal and cleanup.
Fresh vs. Canned: If using fresh pineapple, slice it thin and dry thoroughly to avoid excess moisture affecting the cookie texture.
Add Some Color: Consider placing maraschino cherries on top of the pineapple rings for a classic, nostalgic presentation.
Storage Tips: Keep cookies in an airtight container for up to 3 days or freeze for longer storage. Thaw at room temperature or rewarm in a low oven.

Storage Tips for Pineapple Upside Down Sugar Cookies

Room Temperature: Keep baked cookies in an airtight container at room temperature for up to 3 days to maintain freshness and softness.
Fridge: If your home is particularly warm, you can store the cookies in the fridge for an extra day, ensuring they are tightly wrapped to avoid drying out.
Freezer: For longer storage, freeze cookies in a single layer in a freezer-safe bag or container for up to 2 months.
Reheating: To enjoy that freshly baked taste again, simply thaw at room temperature or warm in a low oven for a few minutes before serving. These Pineapple Upside Down Sugar Cookies are sure to delight even when enjoyed later!

Pineapple Upside Down Sugar Cookies Recipe FAQs

How do I select ripe pineapple for the recipe?
Absolutely! If you’re opting for fresh pineapple, choose one that’s slightly firm but yields a little when pressed. Look for a sweet aroma at the base, and avoid any fruit with dark spots or blemishes.

What is the best way to store Pineapple Upside Down Sugar Cookies?
To keep your cookies fresh, store them in an airtight container at room temperature for up to 3 days. If you live in a warm area, you may choose to refrigerate them, but make sure to wrap them well to prevent drying out.

Can I freeze Pineapple Upside Down Sugar Cookies?
Very! For longer storage, you can freeze the cookies in a single layer on a baking sheet until firm, then transfer them to a freezer-safe bag or container. They’ll last for up to 2 months. To enjoy them later, just thaw at room temperature or warm in a low oven.

What if my cookie dough spreads too much while baking?
If you find that your cookies spread excessively, it might be due to using melted or overly soft butter. Make sure your butter is just softened. If your kitchen is warm, try chilling the dough for about 20 minutes before baking to help maintain shape.

Are there any dietary considerations for Pineapple Upside Down Sugar Cookies?
Yes! If you have allergies, note that this recipe contains butter and eggs. For a vegan option, you can substitute the egg with a chia egg (1 tablespoon chia seeds mixed with 3 tablespoons water, let sit until gel-like). Always check ingredient labels for potential allergens!

Can I use different fruits on top of the cookies?
Absolutely! Feel free to experiment with other fruits like cherries or peaches for a different flavor and presentation. Just ensure that any fresh fruit is thoroughly dried to avoid excess moisture affecting the cookie texture.