Pineapple Upside Down Sugar Cookies

Pineapple Upside Down Sugar Cookies came into my life one sunny afternoon last summer when I was drowning in fresh pineapple and craving something sweet, but didn’t feel like making an entire cake. These cookies are pure genius! They capture all the nostalgic flavors of a classic pineapple upside down cake, but in adorable, hand-held cookie form.

The first batch vanished from my kitchen counter in no time, I had to whip up a second batch the same day! Even my teenage son, who usually turns his nose up at anything “fruity,” devoured five in one sitting and asked if we could add them to our regular baking rotation. That’s when I knew this recipe was something truly special!

Why You’ll Love Pineapple Upside Down Sugar Cookies

• Nostalgic Flavors in Bite-Size Form: All the tropical goodness of pineapple upside down cake without needing a fork
• Crowd-Pleasing Surprise: Everyone expects regular sugar cookies until they spot that gorgeous pineapple and cherry topping
• Make-Ahead Friendly: These actually taste even better the next day as the flavors meld
• Perfectly Portable: Great for picnics, potlucks, and cookie exchanges where you want something unique

Ingredients

For the Sugar Cookie Dough

• Unsalted butter: Creates that rich, tender base that melts in your mouth
• Granulated sugar: Provides the perfect sweetness and helps create those slightly crisp edges
• Egg: Binds everything together while adding richness
• Vanilla extract: That warm, aromatic flavor that enhances everything else
• All-purpose flour: The foundation that gives our cookies structure
• Baking powder: Just enough lift to keep the cookies soft without being cakey
• Salt: The secret ingredient that makes all the sweet flavors pop

For the Pineapple Topping

• Crushed pineapple: Brings that tropical sweetness and signature flavor
• Maraschino cherries: The classic finishing touch that makes these instantly recognizable

Note: The exact measurements for all ingredients will be available in the recipe card below the article.

How to Make These Irresistible Cookies

Step 1: Preheat and Prep

First things first, crank that oven to 350°F and line your baking sheets with parchment paper. This might seem basic, but trust me, that parchment paper is crucial for easy removal, especially with the fruit topping. While the oven’s heating up, drain your crushed pineapple super well. I actually press mine with paper towels to get out as much moisture as possible this prevents soggy cookies later!

Step 2: Create the Perfect Dough

In a large bowl, beat your softened butter and sugar together until it’s light and fluffy. This usually takes 2-3 minutes with an electric mixer, and it’s not a step you want to rush! This creaming process incorporates air into the dough, which gives you that perfect cookie texture. Next, add your egg and vanilla, mixing until everything’s well combined and looking smooth.

Step 3: Add the Dry Ingredients

In a separate bowl, whisk together your flour, baking powder, and salt. This ensures even distribution of the leavening agent. Gradually add this dry mixture to your wet ingredients, mixing just until combined. The key word here is “just” overmixing develops gluten, which can make your cookies tough instead of tender. Your dough should come together nicely without being sticky. If it feels too soft to work with, pop it in the fridge for about 20 minutes.

Step 4: Shape and Fill

Now for the fun part! Scoop tablespoon-sized balls of dough and place them on your prepared baking sheet, leaving plenty of room for spreading. Use your thumb or the back of a measuring spoon to create a nice indentation in the center of each cookie. This little well is where all the pineapple magic will happen! Fill each indentation with about half a teaspoon of your well-drained crushed pineapple, then gently press half a maraschino cherry into the center of each. The combination of the yellow pineapple and bright red cherry creates that classic upside-down cake look that makes these cookies so special!

Step 5: Bake to Perfection

Slide those beauties into your preheated oven and bake for 10-12 minutes. You’re looking for cookies that are just set around the edges with a slight golden color, but still soft in the center. Remember, they’ll continue to firm up as they cool, so it’s better to slightly underbake than overbake. Every oven is different, so start checking at the 10-minute mark.

Step 6: Cool and Set

Let the cookies cool on the baking sheet for about 5 minutes this gives them time to firm up enough to move without breaking. Then transfer them to a wire rack to cool completely. As they cool, the pineapple topping will set up nicely, and the flavors will start to meld together. Try to resist sampling them until they’re fully cooled your patience will be rewarded!

Step 7: Enjoy the Fruits of Your Labor

Once cooled, these cookies are ready to enjoy! The contrast between the buttery sugar cookie base and the sweet-tart pineapple topping is absolutely divine. Each bite gives you that nostalgic pineapple upside down cake experience in perfect cookie form!

Pro Tips for Cookie Perfection

• Butter Temperature Matters: It should be soft enough to leave a slight indentation when pressed, but not melty or greasy
• Pineapple Prep is Key: Really drain that pineapple well excess moisture is the enemy of crisp cookies
• Cherry Hack: Pat the maraschino cherries dry with paper towels to prevent their color from bleeding too much
• Even Sizing: Use a cookie scoop if you have one for uniform cookies that will bake evenly

Flavor Variations to Make These Your Own

Toasted Coconut Topping

Sprinkle some sweetened toasted coconut flakes over the pineapple before baking for a tropical crunch that takes these cookies to the next level. The coconut gets golden and crispy in the oven, adding wonderful texture contrast.

Pineapple Cream Cheese Cookies

Add a small dollop of sweetened cream cheese under the pineapple for a rich, tangy twist that’s reminiscent of cheesecake. Just mix 4 oz of softened cream cheese with 2 tablespoons of sugar and a drop of vanilla.

Brown Sugar Cookie Base

Swap half the granulated sugar with light brown sugar for a deeper, more caramel-like flavor that complements the pineapple beautifully. This simple switch adds a whole new dimension to these cookies.

Lime Zest Infusion

Add a teaspoon of fresh lime zest to the cookie dough for a citrusy brightness that cuts through the sweetness. The lime and pineapple combination is tropical perfection!

Pineapple-Cherry Jam Glaze

For an extra touch of shine and flavor, warm 2 tablespoons of pineapple preserves until melted and brush over the cookies while they’re still warm from the oven. This creates a beautiful glaze that locks in moisture.

Serving Suggestions

These versatile cookies are perfect for so many occasions:

• Summer BBQs and picnics where you want a dessert that doesn’t melt in the heat
• Birthday parties or baby showers for something different than the usual cake
• Easter or Mother’s Day brunch tables where they’ll stand out among traditional offerings
• Afternoon tea or coffee break when you need a little sweet pick-me-up
• Holiday cookie platters where they’ll add a pop of color and unique flavor

They pair beautifully with:

• A light herbal tea like chamomile or mint
• Fresh lemonade for a summer treat
• Sparkling water with a twist of citrus
• A cup of coffee for that perfect sweet contrast

Storage and Freezing Tips

Storage

These cookies keep beautifully in an airtight container at room temperature for up to 3 days. The flavors actually develop and improve overnight, making them perfect for make-ahead treats. For longer storage, pop them in the refrigerator where they’ll stay fresh for up to a week.

Freezing

Yes, you can freeze these tropical delights! Layer the completely cooled cookies between sheets of parchment paper in a sealed container or freezer bag. They’ll keep for up to 2 months in the freezer. When you’re ready to enjoy them, just thaw at room temperature for about an hour.

FAQs

Can I use fresh pineapple instead of canned?
You can, but you’ll need to cook it down a bit first to remove excess moisture. Fresh pineapple tends to be juicier than canned, which could make your cookies soggy.

My cookies spread too much during baking. What went wrong?
This usually happens if the butter was too soft or the dough was too warm. Next time, try chilling the shaped cookies for 15-20 minutes before baking.

Can I make the dough ahead of time?
Absolutely! The dough can be refrigerated for up to 3 days. Just let it sit at room temperature for about 15 minutes to soften slightly before shaping.

How do I know when the cookies are done?
Look for edges that are just turning golden while the centers still look slightly soft. They’ll continue to set as they cool, so it’s better to underbake slightly than overbake.

Conclusion

These Pineapple Upside Down Sugar Cookies are what I call “conversation starter cookies” the kind that make people do a double-take at the dessert table and immediately ask for the recipe. They’re the perfect blend of familiar and unexpected, combining the beloved flavors of a classic dessert with the convenience and charm of a cookie.

What I love most about this recipe is how it transforms a simple sugar cookie into something special with just a few extra ingredients. The buttery cookie base provides the perfect canvas for that sweet-tart pineapple and cherry topping, creating a treat that’s greater than the sum of its parts.

Whether you’re looking to shake up your cookie game, need something unique for a special occasion, or just want to bring a taste of tropical nostalgia to your everyday baking, these cookies deliver on all fronts. So grab your mixing bowl, drain that pineapple well, and get ready to create a new favorite that bridges the gap between classic cake and convenient cookie!