Pineapple Upside Down Sugar Cookies Recipe

If you’ve ever craved all the nostalgia of a classic pineapple upside down cake with the ease and playful fun of cookies, these Pineapple Upside Down Sugar Cookies are going to become your new obsession. Imagine a buttery, golden sugar cookie base topped with caramelized brown sugar, juicy pineapple rings, and a sweet maraschino cherry in the center—each bite is a burst of sunshine, soft crumb, and tropical delight. These cookies deliver big retro dessert flavor in the palm of your hand, marrying the best of both worlds into a treat that’s as beautiful as it is delicious.

Ingredients You’ll Need

Everything in this recipe plays a deliciously important role. Some ingredients are pantry basics, while others add that touch of tropical magic. Here’s exactly what you need to create unforgettable Pineapple Upside Down Sugar Cookies at home:

• Butter (room temperature): Gives the cookies their rich, tender texture and helps cream with sugar for a fluffy base.
• Granulated sugar: Adds classic sweetness and lightness, creating the perfect sugar cookie crumb.
• Eggs: Provide structure and moisture, helping the cookies stay chewy and soft.
• Vanilla extract: Brings out warm, aromatic undertones that complement both cookie and fruit.
• Sour cream: Secret weapon for extra moisture and a hint of tang to balance the sweetness.
• All-purpose flour: The foundation of each cookie, giving it structure while keeping it soft.
• Baking powder: Helps the cookies rise just the right amount—it’s the lift behind every bite.
• Cornstarch: Ensures that signature soft, tender crumb that’s bakery quality.
• Salt: Rounds out all the flavors and prevents the cookies from being cloyingly sweet.
• Canned pineapple slices: Look for slices packed in juice for the juiciest, brightest flavor and color!
• Maraschino cherries: That classic pop of red and sweet fruitiness in every cookie center.
• Butter (melted): Used for making a rich caramel base under the pineapple as they bake.
• Light brown sugar (packed): Brings deep caramel notes to every bite and helps create that iconic sticky topping.

How to Make Pineapple Upside Down Sugar Cookies

Step 1: Prep and Preheat

Start by preheating your oven to 350 degrees F. Set aside your USA pan mini round cake pan—this is key for getting those picture-perfect, bakery-style cookies that bake up thick and round, just like mini cakes. Having your pan ready before you mix ensures nothing interrupts your baking flow.

Step 2: Cream the Butter and Sugar

In a large mixing bowl, combine the room temperature butter and granulated sugar. Use an electric mixer and beat until the mixture looks fluffy and pale, about 2-3 minutes. This step not only dissolves the sugar but creates an airy structure to support the pineapple topping.

Step 3: Mix in Wet Ingredients

Add the eggs, vanilla extract, and sour cream straight into your butter-sugar mixture. Beat again until everything is nicely blended. The sour cream at this stage ensures incredible moisture, making each cookie soft on the inside yet sturdy enough to hold the topping.

Step 4: Add Dry Ingredients

Now, sprinkle in the flour, baking powder, cornstarch, and salt. Mix just until the dough forms—avoid overmixing to keep those Pineapple Upside Down Sugar Cookies perfectly tender. The dough will be thick and luscious!

Step 5: Prepare the Caramel Base

While your dough rests for a minute, grab a separate bowl and stir together the melted butter with the light brown sugar. This dreamy combination is what gives the cookies their gooey, caramelized tops (which, thanks to flipping, become the bottoms) and infuses each with toffee notes.

Step 6: Build the Cookie Bases

Spoon about a tablespoon of the brown sugar mixture into the bottom of each mini pan cavity, spreading it so the bottom is completely coated. This is where the signature caramel layer is born!

Step 7: Add Pineapple and Cherries

Carefully place one pineapple slice on top of the brown sugar mixture in each pan. Pop a maraschino cherry right into the center of each pineapple ring—this gives your Pineapple Upside Down Sugar Cookies that iconic look and a delightful hit of sweetness.

Step 8: Top with Cookie Dough

Use a 3-tablespoon cookie scoop to dollop a mound of sugar cookie dough over each pineapple ring. Gently flatten with an offset spatula so it covers the fruit completely. The dough will spread out a bit in the oven, encasing the caramel and fruit below.

Step 9: Bake

Place the pan in your preheated oven and let the cookies bake for about 25 minutes. You’re looking for golden brown edges and caramel bubbling up the sides—trust your senses! This is when your kitchen will start to smell absolutely irresistible.

Step 10: Flip and Cool

After removing from the oven, let the cookies cool for 10 minutes so they can set up (and so you don’t burn yourself!). Then, invert the cookies onto a wax paper-covered surface. Some caramel might run, so wax paper is a must. If any fruit sticks to the pan, simply place it back on top of the cookie while it’s still warm.

Step 11: Serve and Enjoy

Allow your Pineapple Upside Down Sugar Cookies to cool completely. The flavors settle and develop as they rest, making each bite more delicious. Store them in an airtight container and enjoy within the first two or three days for peak flavor.

How to Serve Pineapple Upside Down Sugar Cookies

Garnishes

Top these cookies with a little sprinkle of toasted coconut, an extra drizzle of caramel, or even a dusting of powdered sugar for an elegant finish. Each option adds a welcome new twist to your Pineapple Upside Down Sugar Cookies without overpowering their classic flavors.

Side Dishes

Pair these cookies with a scoop of vanilla ice cream, a dollop of whipped cream, or even a simple fruit salad. The cool, creamy sides make every bite of the warm, sticky cookie even more special—perfect for a sunny afternoon treat or a nostalgic dessert spread.

Creative Ways to Present

Arrange your Pineapple Upside Down Sugar Cookies on a vintage cake stand, or stack them in a clear glass jar for a playful cookie tower display at potlucks. Individually wrapping each in parchment and twine makes for the sweetest edible gift—imagine the look on your friends’ faces when they see a cookie with its very own pineapple and cherry top!

Make Ahead and Storage

Storing Leftovers

Once completely cooled, store any leftover cookies in an airtight container at room temperature. They keep their moisture and flavor for 2 to 3 days—just be sure to separate the layers with parchment or wax paper to prevent sticking from the caramelized tops.

Freezing

Pineapple Upside Down Sugar Cookies also freeze beautifully! Wrap each cooled cookie individually in plastic wrap, then pop them into a freezer-safe bag or container. Thaw at room temperature when you want a taste of sunshine, and they’ll return to their freshly-baked glory in no time.

Reheating

If you prefer your cookies warm (and who can blame you?), simply reheat a cookie in the microwave for 10 to 15 seconds. This softens the caramel layer and brings out the fruity flavors—an irresistible treat, especially when paired with ice cream.

FAQs

Can I use fresh pineapple instead of canned?

Yes! Just make sure to slice fresh pineapple into rings about the same thickness as canned slices, and pat them dry before using to prevent excess liquid that might affect the texture of your Pineapple Upside Down Sugar Cookies.

What if I don’t have a mini round cake pan?

You can use a muffin tin as a substitute; just slightly trim the pineapple rings to fit. The results are just as delicious and adorable, perfect for sharing or setting out at a party.

How do I keep the pineapple from sticking to the pan?

Make sure to fully coat the bottom of each cavity with the brown sugar-butter mixture. This not only adds flavor but acts as a nonstick barrier that helps the pineapple release easily after baking.

Can I make these cookies gluten-free?

Absolutely! Swap in your favorite 1:1 gluten-free flour blend in place of the all-purpose flour. The cookies remain soft and chewy, and the fruity topping shines just as brightly.

Why do my cookies fall apart when I turn them out?

If the cookies are too warm when you invert them, they might be fragile. Let them cool in the pan for the full 10 minutes, and be gentle when loosening and inverting for perfect Pineapple Upside Down Sugar Cookies every time.

Final Thoughts

There’s something so charming about Pineapple Upside Down Sugar Cookies—they turn a classic dessert into pocket-sized bites of happiness. If you’re ready for a little throwback nostalgia with a playful, modern twist, give these cookies a try. You’ll be hooked from the very first caramel-drizzled, fruit-filled bite!

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