Pineapple Upside-Down Sugar Cookies

If you love classic desserts with a modern twist, then these Pineapple Upside-Down Sugar Cookies will absolutely blow you away. This delightful recipe takes everything you love about the iconic pineapple upside-down cake—caramelized brown sugar, juicy pineapple rings, and sweet maraschino cherries—and brings it into the realm of soft, buttery sugar cookies. These cookies are perfect for summer gatherings, backyard BBQs, or even when you just want a pop of fruity sweetness during the colder months. They’re colorful, flavorful, and packed with that nostalgic, tropical taste you can’t resist. Whether you’re baking for a special event or just treating yourself to something fun, these cookies will steal the show on any dessert table!

Ingredients You’ll Need

🍍 For the Topping:

• 1 can pineapple slices (cut into small chunks or tidbits)
• Maraschino cherries (halved)
• ¼ cup brown sugar
• 2 tbsp unsalted butter (melted)

🍪 For the Sugar Cookie Base:

• 1 cup unsalted butter (softened)
• 1 cup granulated sugar
• 1 egg
• 2 tsp vanilla extract
• 2½ cups all-purpose flour
• ½ tsp baking soda
• ¼ tsp salt

You’ll also want a muffin pan or cookie scoop to shape these beauties perfectly.

How to Make Pineapple Upside-Down Sugar Cookies

Start by preheating your oven to 350°F (175°C). Lightly grease a standard muffin tin or line it with cupcake liners. In each muffin cavity, add a teaspoon of melted butter followed by a sprinkle of brown sugar. Then, place a small piece of pineapple and half a cherry in the center of each.

In a separate bowl, cream the butter and sugar together until light and fluffy. Add in the egg and vanilla, then mix again. Sift in the flour, baking soda, and salt, and mix until a soft dough forms.

Scoop a ball of cookie dough and flatten it slightly. Place the dough over the fruit mixture in the muffin pan and press down gently so it covers everything.

Bake for 12–15 minutes or until the edges of the cookies are lightly golden. Allow to cool in the pan for 10 minutes before carefully flipping each cookie upside down onto a cooling rack. If any fruit sticks to the pan, just scoop it out and place it back on top.

These cookies are best served slightly warm or at room temperature. The sugary pineapple topping gets beautifully sticky and caramelized—pure magic!

Tips for the Best Pineapple Upside-Down Sugar Cookies

🍍 Drain the pineapple well – Excess moisture can make the cookie base soggy. Pat the fruit dry with a paper towel before placing it in the muffin pan.

🧁 Use a nonstick muffin pan – This makes flipping the cookies easier and keeps the pineapple design intact.

🔁 Don’t overbake – The cookies continue cooking in the pan after baking, so remove them when the edges are golden and centers are soft.

🧈 Chill the dough – If the dough feels too soft or sticky, chilling for 20 minutes helps create a cleaner bake and more even browning.

🍒 Keep the fruit centered – This gives the final cookie a clean, polished look when inverted.

These tips help you avoid common issues like sticking, burning, or soggy bottoms. When done right, these cookies are as beautiful as they are delicious.

Why You’ll Love These Cookies

🌟 They’re a mashup of two favorites: sugar cookies and pineapple upside-down cake
🍒 Eye-catching and colorful—perfect for parties or gifting
🥄 Easy to make in a standard muffin tin
🍍 Bursting with tropical flavor
💛 Caramelized brown sugar gives every bite an extra layer of yum

Whether you’re reminiscing about grandma’s pineapple cake or trying something new and playful, these cookies offer all the charm and flavor of a retro dessert with a fun modern spin. Plus, you don’t have to bake an entire cake to enjoy that iconic flavor!

The Science Behind Their Unique Texture

The magic of these cookies lies in the caramelized topping that forms during baking. As the brown sugar and butter melt together under the heat, they form a syrupy glaze that seeps into the bottom of the sugar cookie dough. This not only creates a rich flavor but also gives the cookies a moist, chewy edge. The sugar cookie base, made with the perfect ratio of butter to flour, is soft in the center with lightly crisp edges. Combining high-fat content and minimal leavening keeps the cookies from puffing up too much, ensuring they hold the pineapple and cherry beautifully. The contrast between the warm, juicy fruit and the buttery cookie is what gives these treats their irresistible mouthfeel. It’s science—and sweetness—at its best.

The Magic of Pineapple Upside-Down Sugar Cookies

There’s something nostalgic and comforting about pineapple upside-down desserts, and bringing that essence into a handheld cookie format is just genius. When these cookies are flipped from the pan, they reveal a golden, glossy top crowned with fruit. It’s like unveiling a mini masterpiece every time. The caramelized edges, tropical aroma, and juicy fruit give these cookies a bakery-level presentation without the fuss. They’re magical not just in flavor but in experience. From the sizzle of butter melting in the oven to the moment you take that first gooey bite, these cookies turn ordinary afternoons into special occasions. They’re a delightful surprise for guests and a sweet reward for any day of the week.

FAQs About Pineapple Upside-Down Sugar Cookies

Can I use fresh pineapple instead of canned?
Yes! Just chop it into small chunks and drain well. Make sure it’s not too juicy or it may affect the cookie texture.

Can I make them ahead of time?
Absolutely. Store baked cookies in an airtight container for up to 3 days. You can also refrigerate the dough ahead of time and bake fresh when needed.

Do I need to grease the muffin tin?
Yes—even nonstick pans should be lightly greased or sprayed to help the cookies release cleanly when inverted.

Can I freeze these cookies?
It’s best to freeze the raw dough. You can freeze formed cookie dough balls, then add the topping and bake later. Freezing fully baked cookies with the fruit topping may make them soggy upon thawing.

Do they taste better warm or cold?
They’re delicious both ways, but slightly warm allows the topping to stay gooey and extra flavorful!

Conclusion

Pineapple Upside-Down Sugar Cookies are proof that you can transform a classic dessert into a playful, bite-sized masterpiece. They’re vibrant, flavorful, and full of nostalgic charm, yet easy enough to make on a whim. Whether you’re baking them for family, friends, or just for yourself (no judgment here!), they’re guaranteed to become a new favorite. With their soft sugar cookie base and sweet, caramelized fruit topping, these cookies deliver a tropical getaway in every bite. So grab your muffin pan and a can of pineapple—it’s time to bake up some sunshine!