There’s something truly magical about cookies that can transform ordinary moments into delightful experiences. Imagine pulling a batch of Pineapple Upside Down Sugar Cookies from the oven, their golden edges hugging decadent pineapple rings that glisten under the kitchen lights. These cookies are a whimsical spin on the beloved Pineapple Upside Down Cake, and trust me, they’re just as charming! Each bite is soft, buttery, and bursting with tropical sweetness, creating a delightful symphony of flavors that will transport you straight to a sun-kissed beach in paradise.

Reason to Fall in Love with This Recipe

There are plenty of reasons why these Pineapple Upside Down Sugar Cookies deserve a special place in your heart (and your kitchen!). Allow me to share just a few:

A Unique Twist: They combine the classic joy of sugar cookies with the tropical indulgence of a pineapple upside down dessert, making them a refreshing choice for any gathering.
Easy to Make: Even if baking isn’t your forte, these cookies come together easily. With just a handful of ingredients, you’ll enjoy the satisfaction of homemade cookies without the fuss.
Perfect for Sharing: These cookies are a hit at parties, potlucks, or even just as a treat to brighten someone’s day. Who wouldn’t love a sweet, unexpected surprise?
Customizable: Want to add an extra touch? The simple base of this recipe allows for plenty of experimentation—I’ll share some ideas later!
A Memorable Flavor: The combination of sweet pineapple and brown sugar creates a gourmet flavor that is sure to impress your friends and family.

Your Shopping List

Gathering your ingredients is the first step toward cookie magic! Here’s what you’ll need, along with some helpful notes:

1 cup unsalted butter, softened: This will form the rich base of your cookies and create that soft, melt-in-your-mouth texture.
1 cup granulated sugar: For sweetness that balances wonderfully with the tropical flavors.
1 egg: Enhances moisture and binds the ingredients beautifully.
1 tsp vanilla extract: A splash of vanilla adds a lovely warmth to the cookies.
2½ cups all-purpose flour: The structure of your cookie; it holds everything together.
½ tsp baking soda: This will help the cookies rise, giving them that delightful puff.
¼ tsp salt: Just a pinch to enhance all the flavors.
10–12 canned pineapple rings, well-drained and patted dry: The star of the show! Make sure they are dry to prevent sogginess.
Additional sugar for sprinkling: For a sweet touch on top of each cookie.

Crafting Your Perfect Pineapple Upside Down Sugar Cookies

Ready to get those delicious cookies baking? Here’s how to make them step by step. Don’t worry; I’ll guide you through this cookie journey!

Preheat your oven to 350°F (175°C). This creates the perfect baking environment for those cookies to spread out and become tender.
Line baking sheets with parchment paper. This will prevent sticking and make cleanup a breeze.
In a large bowl, cream together the softened butter and granulated sugar using an electric mixer until it’s light and fluffy. This should take about 2-3 minutes. It’s the perfect time to show off those arm muscles if you’re mixing by hand!
Beat in the egg and vanilla extract until everything is well combined. The mixture should be beautiful and smooth.
In a separate bowl, whisk together the flour, baking soda, and salt. This ensures the leavening agent is evenly distributed throughout the flour, setting you up for success.
Gradually add the dry ingredients to the butter mixture, combining until you form a soft dough. Don’t over-mix; you want to keep that texture lovely and light.
Now comes the fun part! Roll the dough into 1½ tablespoon-sized balls, then flatten them slightly with your hands. Place these on your prepared baking sheet.
Top each dough disk with a pineapple ring, pressing down gently. Make sure that the pineapple becomes part of the cookie, but not so much that it squishes out the sides.
Sprinkle a little more sugar on top of each pineapple. This will create that delightful sparkle and an extra layer of sweetness.
Bake for 12–14 minutes, or until the edges are lightly golden. Keep an eye on them—nobody wants burnt cookies!
Once they’re out of the oven, let them cool for about 5 minutes on the sheet before transferring them to a wire rack to cool completely. The aroma wafting through your kitchen will be absolutely divine!

Secrets to Cookie Success

While these cookies are pretty straightforward, I can’t resist sharing some pro tips to ensure your batch is nothing short of perfection:

Butter Matters: Make sure your butter is truly softened, but not melted. It should still hold its shape when you scoop it.
Pineapple Prep: Drain the pineapple thoroughly and pat it dry to avoid soggy cookies. Nobody wants a wet cookie!
Watch Your Time: Keep an eye on the cookies in the last couple of minutes of baking. Every oven is a little different, and you want that perfect golden edge!
Cool Down: Allow them to cool on the baking sheet shortly before transferring. This helps them set perfectly, preventing breakage.

Creative Twists on a Classic

Let’s get adventurous! Here are some ways you can mix it up with these delightful cookies:

Coconut Add-In: Add shredded coconut for a tropical flair that complements the pineapple beautifully.
Spice It Up: Introduce a pinch of cinnamon or nutmeg to the dough for a warm, cozy flavor.
Chocolate Drizzle: Drizzle melted chocolate over the cooled cookies for an extra decadent treat.
Rum Flavor: Enhance the tropical vibe with a splash of rum extract for a delightful twist.
Use Fresh Pineapple: If you have fresh pineapple on hand, grill it lightly before adding it to the cookies. It will intensify the flavors beautifully!

Presenting Your Masterpiece

When it comes to enjoying your Pineapple Upside Down Sugar Cookies, presentation matters! Arrange them on a colorful platter, maybe with a few mint leaves for a touch of freshness. Pair them with a scoop of coconut ice cream for an indulgent treat that brings a cool contrast to the warm, buttery cookies. They’re a perfect sweet ending to a summer barbecue or a cozy family dinner.

Keeping Them Fresh

Wondering how to store your cookies? Here’s what to do to keep your delicious creation fresh for as long as possible:

Room Temperature: Store cookies in an airtight container at room temperature for about 3-4 days. They’ll stay soft and tasty!
Refrigeration: If your kitchen tends to be warm, you might want to pop them in the fridge. Just remember to let them sit out for a few minutes to reach their lovely chewy texture again.
Freezing: For longer storage, freeze them in a single layer on a baking sheet, then transfer to an airtight container for up to three months. Allow them to thaw at room temperature before enjoying.

Your Questions Answered

Can I use fresh pineapple instead of canned?
Absolutely! Just be sure to pat it dry and slice it into rings or small pieces, and grilling them lightly can add a beautiful caramel flavor.
What if my dough is too sticky?
If your dough feels sticky, adding a bit more flour can help. But be careful not to add too much, as this can alter the texture!
Can I double the recipe?
For sure! Just keep an eye on the baking time, as larger batches may require an extra minute or two in the oven.
What can I do with any leftover sugar?
Any extra sugar can be stored in a sealed container for your next baking adventure. It’s perfect for sprinkling on muffins, cookies, or even in a cup of tea!

Embrace the spirit of baking, and let your kitchen fill with the aromas of these beautiful cookies. Pineapple Upside Down Sugar Cookies are not just a recipe; they are an invitation to create joyful memories, share sweetness, and enjoy the little moments that matter most. I hope you’ll give this recipe a try and find as much joy in baking them as I do!

Pineapple Upside Down Sugar Cookies

Delightful cookies combining the classic joy of sugar cookies with the tropical indulgence of pineapple upside down dessert, perfect for any gathering.

Print Recipe Pin Recipe

Prep Time 15

Cook Time 14

Total Time 29

Servings: 24 cookies

Course: Dessert, Snack

Cuisine: American, Tropical

Calories: 150

Ingredients Method Notes

Ingredients

Cookie Base

1 cup unsalted butter, softened This will form the rich base of your cookies.
1 cup granulated sugar For sweetness that balances with tropical flavors.
1 large egg Enhances moisture and binds ingredients.
1 tsp vanilla extract Adds warmth to the cookies.
2.5 cups all-purpose flour Holds everything together.
0.5 tsp baking soda Helps the cookies rise.
0.25 tsp salt Enhances all the flavors.
10-12 pieces canned pineapple rings, well-drained and patted dry The star of the show!
to taste tablespoons additional sugar for sprinkling For a sweet touch on top.

Method

Preparation

Preheat your oven to 350°F (175°C).
Line baking sheets with parchment paper.
In a large bowl, cream together the softened butter and granulated sugar using an electric mixer until light and fluffy, about 2-3 minutes.
Beat in the egg and vanilla extract until well combined.
In a separate bowl, whisk together the flour, baking soda, and salt.
Gradually add the dry ingredients to the butter mixture until you form a soft dough.
Roll the dough into 1½ tablespoon-sized balls and flatten them slightly.
Place the dough on the prepared baking sheet and top each disk with a pineapple ring, pressing down gently.
Sprinkle sugar on top of each pineapple.

Baking

Bake for 12-14 minutes, or until edges are lightly golden.
Let cool for about 5 minutes on the sheet before transferring to a wire rack.

Notes

Ensure butter is softened well but not melted. Drain and pat pineapple dry to avoid sogginess. Watch baking carefully to avoid burning.