Name: Pineapple Upside Down Sugar Cookies
Prep time: 15 min
Cook time: 13 min
Total time: 28 min
Ingredients: 1 cup Unsalted Butter, softened; 1 cup Granulated Sugar; 1 large Egg; 1 teaspoon Vanilla Extract; 2 cups All-Purpose Flour; 1 teaspoon Baking Soda; 1/2 teaspoon Salt; 10-12 rings Canned Pineapple, well-drained and patted dry; to taste Additional Sugar for Sprinkling

Jump to Recipe

Looking for a treat that’s both nostalgic and refreshingly new? Pineapple Upside Down Sugar Cookies capture the sweet, caramelized goodness of classic pineapple upside down cake, but in a cute, handheld cookie. Imagine biting into a tender, buttery sugar cookie topped with a juicy pineapple ring — every bite is a burst of sunny flavor that’s equal parts fun and satisfying. Did you know upside down cakes became trendy in the 1920s, thanks in part to the rise of canned pineapple? Fast forward to today, and these cookies borrow that retro charm while cutting down on the mess and prep time.

What makes this recipe special is how quickly it comes together, making it perfect for busy families and last-minute entertaining. Unlike traditional pineapple upside down cake, which can be fussy or time-consuming, these cookies are so simple even kids can help! If you liked my Chewy Chocolate Chip Banana Cookies, you’ll love these for their playful twist on classic comfort. Let’s jump in and make snack time just a little more sunshine-filled!

What is Pineapple Upside Down Sugar Cookies?

Ever wondered what would happen if a sugar cookie met a pineapple upside down cake? Well, Pineapple Upside Down Sugar Cookies is the clever and delicious result! The name might sound like a culinary riddle — are the cookies upside down, or is the pineapple? Spoiler: it’s both and neither! It’s basically all the pineapple-cakey goodness you love “turned upside down” right onto a sugar cookie. Remember the old saying, “the way to a man’s heart is through his stomach”? It definitely holds true here. These cookies are sure to win hearts wherever they go. Why not bake a batch and see for yourself just how irresistible they are?

Why You’ll Love This Recipe

There are plenty of reasons to make Pineapple Upside Down Sugar Cookies your new favorite dessert! The main highlight? Each cookie combines soft, buttery sugar cookie dough with caramelized pineapple for an irresistible taste experience — a little tropical getaway in every bite. Plus, making these at home is a real money-saver compared to picking up a bakery treat; you’ll get more cookies for less, and the homemade touch always tastes better. The best part might be those gorgeous pineapple rings baked right on top, adding both flavor and eye-catching appeal. If you’ve enjoyed my Strawberry Jam Thumbprint Cookies before, you’ll appreciate how these cookies take the concept of “fruit-topped sweet treats” up a notch. Ready to thrill your taste buds? Let’s get baking!

How to Make Pineapple Upside Down Sugar Cookies

Quick Overview

Pineapple Upside Down Sugar Cookies are incredibly easy to make, taking just about 30 minutes from start to finish. With minimal prep time and straightforward ingredients, you’ll have a batch cooling on your counter in no time. The simple sugar cookie base means no chilling or rolling, and the caramelized pineapple topping adds a pop of color and flavor. These cookies are perfect for a family treat, bake sale, or fun dessert with friends.

Ingredients

1 cup unsalted butter, softened
1 cup granulated sugar
1 large egg
1 teaspoon vanilla extract
2 cups all-purpose flour
1 teaspoon baking soda
1/2 teaspoon salt
10-12 canned pineapple rings, well-drained and patted dry
Additional sugar for sprinkling

Step-by-Step

Preheat your oven to 350°F (180°C). Line baking trays with parchment paper for easy cleanup.
Using a large mixing bowl, cream together the softened butter and sugar until light and fluffy. This should take about 2-3 minutes with an electric mixer.
Beat in the egg and vanilla extract until well combined and smooth.
In a separate bowl, whisk together flour, baking soda, and salt. Gradually add the dry ingredients to the wet ingredients, mixing just until a soft dough forms.
Scoop about 2 tablespoons of dough per cookie onto the prepared baking trays, spacing them 2 inches apart.
Gently press a dried pineapple ring onto each mound of cookie dough, flattening slightly. If the rings are very large, you can trim or halve them to fit.
Sprinkle a bit of granulated sugar over the pineapple tops for a touch of sparkle and caramelization.
Bake for 11-13 minutes, or until the cookies are lightly golden around the edges and set in the center.
Allow cookies to cool on the baking tray for a few minutes before transferring to a wire rack to cool completely. Enjoy!

What to Serve Pineapple Upside Down Sugar Cookies With

To round out your dessert table, serve these cookies alongside a scoop of vanilla bean ice cream or a dollop of freshly whipped cream. For a pretty presentation, a few maraschino cherries in the center of each pineapple ring can add both color and a sweet finish. If you’re hosting a party, consider pairing them with tropical fruit punch or coconut milk lattes for a vacation vibe. They also make a delightful companion to cold brew coffee or an afternoon cup of tea.

Top Tips for Perfecting Pineapple Upside Down Sugar Cookies

Make sure your pineapple rings are well-drained and patted completely dry. Excess moisture can make the cookies soggy.
Don’t overmix the dough once the flour is added. This keeps the cookies tender and soft.
If you want some extra caramelization, sprinkle a little brown sugar on top of the pineapple along with the granulated sugar.
For smaller cookies or a fun variation, cut the pineapple rings into smaller pieces and press them into mini cookie dough mounds.
If you prefer, you can substitute canned pineapple tidbits for rings; just press a few pieces onto each cookie and proceed as directed.

Storing and Reheating Tips

Store Pineapple Upside Down Sugar Cookies in an airtight container at room temperature for up to 3 days. If you’d like them to stay soft even longer, add a slice of bread to the container (it’ll help retain moisture). For longer storage, freeze cookies in a single layer until solid, then transfer to a zip-top freezer bag. They’ll keep in the freezer for up to 2 months. To enjoy from frozen, simply thaw at room temperature for about 30 minutes or warm gently in a low oven for a few minutes until soft.

FAQs

Can I use fresh pineapple instead of canned?
Yes, just slice the pineapple thinly and pat it very dry before adding to the cookies.

Can I make the dough ahead of time?
Absolutely! Chill the dough for up to 48 hours in the fridge, then scoop and bake when ready.

Do I need to grease the baking trays if I use parchment paper?
No, parchment paper prevents sticking, so greasing isn’t necessary.

Can I add cherries like classic upside down cake?
Of course! Add a maraschino cherry to the center of each pineapple ring before baking for an authentic look and taste.

My cookies spread too much — how can I fix this?
Be sure your butter isn’t too soft or melted, and try chilling the dough for 20 minutes before baking if your kitchen is warm.

Conclusion

Pineapple Upside Down Sugar Cookies are simple, show-stopping, and utterly delicious — the perfect blend of comforting sugar cookie and the cheerful brightness of pineapple. Whether you’re new to baking or a seasoned cookie enthusiast, this recipe proves you don’t need a complicated cake pan (or a lot of time!) to wow your friends and family. Their unique look and classic flavor are sure to bring some sunshine to your kitchen, no matter the season. Give them a try, and don’t forget to check out more tropical-inspired desserts on the blog for your next baking adventure!