Pineapple Upside Down Sugar Cookies Recipe

If you’re anything like me, sometimes you just want a cookie that’s a little unexpected—but still comforting and sweet. That’s exactly why I love this Pineapple Upside Down Sugar Cookies Recipe. They bring all the classic charm of a pineapple upside down cake into a fun, handheld cookie you can bake in under 40 minutes. I first made these on a whim for a summer BBQ, and everyone absolutely devoured them, which instantly made them a staple in my recipe box.

What makes this Pineapple Upside Down Sugar Cookies Recipe really shine is how perfectly the buttery sugar cookie base balances with the tangy sweetness of pineapple rings. Plus, that sprinkle of sugar on top caramelizes just enough to give each bite a subtle crunch. If you want a dessert that’s easy to share, looks gorgeous on a platter, and won’t have you slaving away all day, this recipe’s definitely the one to bookmark.

Ingredients You’ll Need

These ingredients come together simply but thoughtfully, ensuring a cookie that’s tender and flavorful with that tropical pineapple twist. When shopping, I recommend getting canned pineapple rings packed in juice rather than syrup for a fresher fruit taste without added sweetness.

• Unsalted butter: Softened butter gives the dough that perfect tender crumb without overpowering the pineapple flavor.
• Granulated sugar: This sweetens the dough and adds slight crispness when baked.
• Large egg: Helps bind everything and adds richness.
• Vanilla extract (optional): I love this for a hint of warmth, but you can skip it if you want the pineapple to really stand out.
• All-purpose flour or gluten-free blend: Choose your preference; either works well, but gluten-free blends might need slight adjustments for texture.
• Baking soda: Gives the cookies a bit of lift for that perfect soft bite.
• Salt: Just a pinch to balance the sweetness and bring out flavors.
• Canned pineapple rings: Be sure to drain these well to keep the dough from getting soggy.
• Additional sugar for sprinkling: This goes on top of the pineapple for a lovely caramelized crust.

Variations

I’ve played around with this Pineapple Upside Down Sugar Cookies Recipe a few different ways, and it’s fun to personalize depending on your mood or the occasion. Don’t be afraid to make it your own!

• Tropical Twist: Adding a sprinkle of toasted coconut flakes on top after baking gives these cookies an extra island vibe that I adore.
• Gluten-Free Version: I swapped out all-purpose flour for a gluten-free blend one time, and with a slight increase in baking time, they came out just as delicious.
• Mini Cookies: For a party, I made bite-sized versions—perfect for popping in your mouth and serving on platters.
• Spiced Variation: Toss in a pinch of ground cinnamon or nutmeg for some warming spice notes.

How to Make Pineapple Upside Down Sugar Cookies Recipe

Step 1: Prepare Your Tools and Preheat

I always start by lining my baking trays with parchment paper—this means no sticky mess later and easy cleanup. Preheat your oven to 350°F (180°C) so it’s ready to go when your dough is mixed. Trust me, it makes everything more seamless.

Step 2: Cream Butter and Sugar

Using a hand or stand mixer, cream the softened unsalted butter and granulated sugar together. You’re looking for a light, fluffy texture—this usually takes about 2-3 minutes. This step is key because it gives your cookies a soft, melt-in-your-mouth texture.

Step 3: Mix in Egg and Vanilla

Next, add your large egg and vanilla extract if you’re using it. Beat everything well until the mixture looks smooth and fully combined. The egg adds richness and structure so your cookies hold shape nicely.

Step 4: Combine Dry Ingredients and Make Dough

In a separate bowl, whisk together the flour, baking soda, and salt. Slowly add these dry ingredients to your wet mixture, mixing until you get a soft cookie dough that isn’t too sticky. If your dough feels too wet, add a bit more flour, a tablespoon at a time.

Step 5: Shape and Top with Pineapple

Scoop about 2 tablespoons of dough per cookie and place them spaced out on your lined trays. Don’t crowd them—they’ll spread a tiny bit but not much. Take a well-drained pineapple ring and gently press it on top of each dough mound, flattening slightly so the cookie bakes around it evenly.

Step 6: Sprinkle Sugar and Bake

Generously sprinkle additional sugar over each pineapple ring—this little extra step is what gives you that caramelized, sparkly finish. Bake for 11-13 minutes until the cookie edges turn golden but the centers still feel just set. Keep an eye on them because ovens vary, and no one wants overbaked pineapple cookies.

Step 7: Cool and Enjoy

Let your cookies cool on the tray for a few minutes; this helps them firm up enough to move without falling apart. Then transfer to a wire rack for full cooling. These are best enjoyed slightly warm, but they hold their magic even after they’ve fully cooled.

How to Serve Pineapple Upside Down Sugar Cookies Recipe

Garnishes

I like to add a tiny dusting of powdered sugar or a drizzle of warm vanilla glaze if I’m serving these at a brunch or party. Fresh mint leaves also give a pop of color and a refreshing touch that balances the sweetness nicely. For a grown-up twist, a hint of shaved dark chocolate works wonders too.

Side Dishes

These cookies pair beautifully with a scoop of vanilla bean ice cream or a dollop of whipped cream if you’re indulging. And for a lighter option, I love serving them with a fresh fruit salad or tropical smoothie. Seriously, it turns snack time into a little mini-vacation.

Creative Ways to Present

When I made these for a recent summer party, I arranged them on a wooden board surrounded by pineapple wedges and tropical leaves, which made the table look so inviting. You could also stack them like mini cookie towers tied with twine for gift-giving. Little touches like edible flowers or colorful sprinkles brighten things up for festive occasions.

Make Ahead and Storage

Storing Leftovers

I store any leftovers in an airtight container at room temperature for up to three days, but honestly, they rarely last that long around here! If you want to keep that just-baked texture longer, layering them between sheets of parchment prevents sticking and keeps the cookies fresh.

Freezing

These cookies freeze wonderfully. I like to freeze them after they’ve completely cooled, packed tightly in a freezer-safe container or zip-top bag. When craving them later, I just thaw at room temperature for about 20-30 minutes, and they taste almost as fresh as straight from the oven.

Reheating

If you have leftovers or frozen cookies, reheating them for 5-7 minutes at 325°F (163°C) in the oven revives their buttery softness and caramelized top. Just keep an eye so they don’t dry out. Microwave works in a pinch but can affect texture, so oven reheating is my go-to.

FAQs

Final Thoughts

This Pineapple Upside Down Sugar Cookies Recipe holds a special place in my heart because it’s simple, joyful, and perfect for sharing anytime you want something sweet with a twist. It’s that rare recipe that lightens up summer days and cozy afternoons alike. I truly hope you give it a go—and when you do, be prepared for compliments and maybe a few recipe requests. Trust me, it’s a winner worth making over and over!

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