Pineapple Upside Sugar Cookies – Tropical Cookie Perfection

First off, thank you so much for being here. Whether you’re a regular reader of my recipe posts or someone who stumbled in from a late-night cookie craving (been there!), I’m genuinely grateful you stopped by. Today’s recipe is a celebration of tropical flavor and vintage charm—a delicious mashup of soft, chewy sugar cookies and the gooey, golden glory of pineapple upside-down cake. These Pineapple Upside Sugar Cookies bring sunny flavor, a hint of caramel, and a whole lot of joy in every bite.

This is one of those recipes I made on a whim and now can’t stop dreaming about. The rich brown sugar glaze, the sweet and tart pineapple, the burst of cherry, and that perfect sugar cookie base come together in such a fun, photogenic, and totally satisfying dessert. It’s like a vacation baked into a cookie.

Why You’ll Love These Pineapple Upside Sugar Cookies

These cookies are exactly what happens when a classic pineapple upside-down cake meets soft, buttery sugar cookies—and it’s pure magic. They’re easy to make, impossible to forget, and the kind of thing people beg you to bring to every gathering.

Reasons to Love This Recipe

• You only need basic pantry staples and one baking sheet.
• No special baking skills required—this one’s friendly for all levels.
• The flavor is rich, tropical, and comforting all at once.
• They smell absolutely divine while baking.
• The presentation is naturally beautiful. That glossy pineapple topping with a cherry center is picture-perfect.

What Do They Taste Like?

Each bite delivers the ultimate contrast—chewy cookie base with buttery, caramelized brown sugar, a tangy slice of pineapple, and the sweet pop of a cherry. The edges are slightly crisp, the center is tender, and the topping? Gooey and golden, like a little sunshine crown on each cookie. It’s like island vacation vibes, but baked.

Benefits of the Recipe

• It’s an easy twist on a classic dessert.
• Ready in under 30 minutes from start to finish.
• Kids love helping assemble them.
• Great for bake sales, potlucks, or just to satisfy your own tropical dessert craving.
• The dough doesn’t need to be chilled.

Ingredients (Makes 12 Large Cookies)

For the Topping:

• 6 pineapple rings, cut in half
• 12 maraschino cherries
• ¼ cup brown sugar
• 2 tablespoons butter, melted

For the Cookie Dough:

• ½ cup butter, softened
• ½ cup granulated sugar
• ½ cup brown sugar
• 1 large egg
• 1 teaspoon vanilla extract
• 1½ cups all-purpose flour
• ½ teaspoon baking soda
• ¼ teaspoon salt

Tools You’ll Need

• A large baking sheet
• Parchment paper or silicone baking mat
• Mixing bowls
• Electric hand or stand mixer (or a strong arm and wooden spoon)
• Measuring cups and spoons
• Silicone spatula
• Cooling rack
• A small spoon or scoop for placing the topping

Ingredient Additions and Substitutions

This is a very flexible cookie recipe. Want to customize the flavor even more? Try these delicious ideas:

• Coconut: Add ¼ cup shredded coconut to the dough for a more tropical, chewy texture.
• Rum Extract: Swap ½ teaspoon of vanilla with rum extract for a grown-up twist.
• Fresh Pineapple: Yes, you can use fresh pineapple. Just be sure to slice it thin and pat dry well with a paper towel to avoid too much moisture.
• Cherries: If you’re not a fan of maraschino cherries, try using dried cherries, frozen (and thawed) tart cherries, or skip them altogether.

How to Make Pineapple Upside Sugar Cookies

Step 1: Preheat the Oven

Start by preheating your oven to 350°F (175°C). Line your baking sheet with parchment paper or a silicone baking mat. This is key to preventing the caramelized topping from sticking.

Step 2: Make the Cookie Dough

In a mixing bowl, cream together the softened butter, granulated sugar, and brown sugar until the mixture is light and fluffy. This should take about 2 to 3 minutes with an electric mixer.

Add the egg and vanilla extract and continue to beat until everything is well incorporated.

In a separate bowl, whisk together the flour, baking soda, and salt. Gradually mix the dry ingredients into the wet mixture just until combined. Don’t overmix—stop as soon as the dough holds together.

Set aside the dough while you prepare the topping.

Step 3: Prepare the Fruit Topping

In a small bowl, stir together the brown sugar and melted butter until smooth. On your lined baking sheet, spoon about a teaspoon of this mixture where each cookie will go—spacing them at least 2 inches apart.

Press half a pineapple ring into each spot. Place a cherry in the center of the ring. This forms the beautiful upside-down topping that will be revealed once the cookies are flipped.

Step 4: Assemble the Cookies

Scoop about 2 tablespoons of cookie dough and place it directly on top of each pineapple ring. Gently flatten the dough just a bit with the back of a spoon or your fingers.

Step 5: Bake

Bake for 12 to 14 minutes or until the edges are golden brown. The cookies should still look soft in the center—they’ll firm up as they cool.

Let them cool on the baking sheet for about 5 minutes. Then, using a thin spatula, carefully flip each cookie upside-down onto a cooling rack. The buttery sugar glaze should have created a glossy caramel top, beautifully showcasing the fruit.

What to Serve With These Cookies

These cookies are indulgent enough to stand alone, but they also pair beautifully with:

• A scoop of coconut or vanilla bean ice cream
• A cup of spiced chai or tropical iced tea
• A fizzy, fruit-forward mocktail
• A light sorbet or frozen yogurt
• Or try them alongside these delightful Vodka Marshmallow Pops for a party dessert spread that screams summer fun

Expert Tips for Success

• Dry your pineapple rings: Blot them gently with a paper towel to reduce excess moisture. This helps prevent soggy cookies.
• Use parchment or a silicone mat: The caramelized topping will stick to bare pans.
• Flip gently: Wait the full 5 minutes after baking before flipping, and use a flat, thin spatula to keep the fruit intact.
• Don’t overbake: Take them out when the edges are golden, not brown. The centers will set as they cool.
• Customize the size: Want mini cookies? Use pineapple tidbits and a smaller scoop of dough to make bite-sized versions.

Storage Instructions

Store any leftover cookies in an airtight container:

• At room temperature: Up to 3 days, best eaten fresh.
• In the refrigerator: Up to 5 days if your kitchen is warm.
• In the freezer: The dough can be frozen before baking. For best results, assemble the topping fresh.

These cookies are best enjoyed the day they’re made, but they’re still delicious as leftovers. Just let them come back to room temperature before serving.

Frequently Asked Questions

Can I use canned pineapple?

Yes! Just drain it well and pat the rings dry with paper towels. This prevents excess moisture from soaking into the cookie.

Can I freeze these cookies?

You can freeze the cookie dough for future baking, but I don’t recommend freezing the fully baked cookies due to the fruit topping.

Do I have to flip them?

Yes—flipping is what creates the “upside-down” look, revealing the caramelized fruit topping. It’s not just for show; it’s part of the magic.

Can I make these gluten-free?

Absolutely! Substitute a 1-to-1 gluten-free flour blend for the all-purpose flour. Just check that your baking soda and other ingredients are gluten-free.

Are they overly sweet?

They’re rich and sweet like most upside-down desserts, but the tang from the pineapple balances things out nicely. If you’re sensitive to sweetness, you can reduce the sugar in the cookie dough slightly.

Wrapping It Up

There’s something special about this recipe that I keep coming back to. Maybe it’s the nostalgic feel of pineapple upside-down cake, or the surprise of flipping over each cookie to reveal that stunning fruit top. Maybe it’s just how good they smell while baking—like a sunny breeze from the tropics wafting through your kitchen. Whatever it is, these Pineapple Upside Sugar Cookies are officially in my permanent dessert rotation.

They’re perfect for everything from summer parties to after-school treats to a whimsical date night dessert. So go ahead—bake up a little edible sunshine and let me know how it turns out.

Looking for more fun, fruity, and playful dessert ideas? Check out these other unique recipes:

• Try these nostalgic Root Beer Cupcakes for an old-fashioned soda fountain flavor in cupcake form.
• Dive into something colorful and creamy with this Fruity Pebbles Cheesecake—perfect for birthdays or just a fun weekend baking project.
• Or keep the tropical party going with these boozy and fun Vodka Marshmallow Pops.

Share Your Creations

If you try this recipe, I would love to hear about it. Leave a review or a comment with your thoughts, or tag your photo on Pinterest. It brings me so much joy to see your kitchen creations come to life.

Nutritional Information (Per Cookie – Approximate)

• Calories: 210
• Total Fat: 10g
• Saturated Fat: 6g
• Carbohydrates: 29g
• Sugar: 18g
• Protein: 2g
• Fiber: Less than 1g

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