Pineapple Upside Down Sugar Cookies Recipe

If you’ve been craving a treat that’s as beautiful as it is delicious, you’re in for something spectacular with Pineapple Upside Down Sugar Cookies. Imagine all the nostalgic charm of a classic pineapple upside down cake, reimagined into soft, buttery sugar cookies with caramelized brown sugar, juicy pineapple, and a cherry on top. This recipe combines the tropical magic of pineapple with the irresistible comfort of your favorite bake sale cookie, and every bite is a little party. Whether you’re treating yourself or surprising friends, Pineapple Upside Down Sugar Cookies bring a showstopping twist to dessert time!

Ingredients You’ll Need

The magic of Pineapple Upside Down Sugar Cookies comes from a set of straightforward, easy-to-find ingredients. Each one plays a starring role in creating those classic layers of flavor and texture—don’t skip on quality, and you’ll taste the difference!

• Butter (room temperature): Key to that soft, melt-in-your-mouth texture and gives the cookies rich flavor.
• Granulated sugar: Adds the perfect sweetness and helps the cookies spread just right.
• Eggs: Act as a binding agent and make the cookies tender and chewy.
• Vanilla extract (2 tsp): This amps up the aroma and deepens the bakery-style flavor—don’t skip it!
• Sour cream: The secret to extra-moist, pillowy cookies with a little tang for balance.
• All-purpose flour (3 cups): A sturdy base to hold up those tropical toppings and provide perfect thickness.
• Baking powder (1 tsp): Lifts the dough so the cookies bake up fluffy, not dense.
• Cornstarch (1 tsp): Keeps the crumb soft and delicately tender.
• Salt (1/2 tsp): Awakens all the other flavors for cookies that really sing.
• Canned pineapple slices (13): Juicy, golden, and perfectly round for that signature upside down effect.
• Maraschino cherries (13): Pop one in each cookie’s center for a punch of color and sweetness.
• Butter, melted (1/2 cup): Mixes with brown sugar to create that unforgettable caramelized bottom layer.
• Light brown sugar, packed (1 cup): The foundation of that sticky, gooey topping everyone loves.

How to Make Pineapple Upside Down Sugar Cookies

Step 1: Prep the Oven and Pan

Preheat your oven to 350 degrees so it’s ready to go once the dough and toppings are assembled. Line up your mini round cake pan (or muffin tin, if you don’t have the special pan) and set aside—the right pan helps create that iconic shape for Pineapple Upside Down Sugar Cookies!

Step 2: Cream the Butter and Sugar

In a large bowl, beat together the room temperature butter and granulated sugar until the mixture is light, fluffy, and pale in color. This step is crucial—it whips air into the dough, leading to those soft and tender cookies that everyone loves.

Step 3: Mix in the Eggs, Vanilla, and Sour Cream

Add the eggs, vanilla extract, and sour cream to the butter and sugar. Mix until the batter is completely combined. The sour cream gives these Pineapple Upside Down Sugar Cookies their pillowy, cloud-like texture with just a hint of tang.

Step 4: Add the Dry Ingredients

Gently mix in the flour, baking powder, cornstarch, and salt. Stir just until everything comes together—overmixing can make your cookies tough, so go easy! The dough should be thick and a little sticky, just perfect for scooping.

Step 5: Prepare the Caramelized Bottom

Grab a small bowl and stir together the melted butter and packed light brown sugar. Spoon about a tablespoon of this sweet, buttery mixture into the bottom of each cake pan cavity. Spread it around to cover the bottom—the goal is to create a luscious, gooey base for the pineapple and cherry.

Step 6: Assemble the Pineapple and Cherry Toppings

Place one pineapple slice atop the brown sugar mixture in each pan cavity. Nestle a maraschino cherry right into the center of the pineapple. Not only do these add flavor, but they turn every cookie into an edible work of art!

Step 7: Add the Cookie Dough and Bake

Using a 3-tablespoon cookie scoop, dollop the prepared cookie dough right on top of the pineapple and cherry in each pan cavity. Use an offset spatula or the back of a spoon to gently spread and flatten the dough across the top. Bake for about 25 minutes, or until the edges are golden and you can see the brown sugar bubbling up the sides.

Step 8: Cool and Invert

Allow the cookies to cool in the pan for about 10 minutes. Carefully turn them out onto a surface covered with wax paper—this catches all that molten brown sugar! If any pineapple slices stick, simply lift them out and reposition atop each cookie. Let the Pineapple Upside Down Sugar Cookies cool completely before enjoying their caramelized magic.

How to Serve Pineapple Upside Down Sugar Cookies

Garnishes

The best way to finish these is with a little flourish! Dust your Pineapple Upside Down Sugar Cookies with a touch of powdered sugar, garnish with fresh mint leaves, or even drizzle a little white chocolate for a fancy upgrade. The gleaming maraschino cherry already offers plenty of cheerful color, but a creative garnish brings your cookies totally over the top.

Side Dishes

For a party platter, serve these cookies alongside a cold fruit salad, vanilla bean ice cream, or a light sorbet. Their caramelized pineapple flavor pairs beautifully with citrus or berry sides. Pineapple Upside Down Sugar Cookies also go well with a tall glass of iced tea or a mug of rich, hot coffee for something a little cozier.

Creative Ways to Present

Try packaging each cookie in a cellophane bag with a ribbon for party favors or holiday gifts—everyone loves receiving these sunny treats! For gatherings, arrange Pineapple Upside Down Sugar Cookies on a big white platter, or stack them on decorative cake stands for a bakery shop look. They even make a playful addition to afternoon tea or a tropical-themed brunch platter.

Make Ahead and Storage

Storing Leftovers

Any leftover Pineapple Upside Down Sugar Cookies should be stored in an airtight container at room temperature. They’re at their absolute best within the first 2 to 3 days, before the pineapple begins to soften the cookie too much. If you need to layer them, place parchment or wax paper between cookies to keep them from sticking together.

Freezing

To freeze, let the cookies cool completely. Then lay them out on a baking sheet to freeze individually so they don’t stick. Once firm, transfer Pineapple Upside Down Sugar Cookies to a zip-top freezer bag or airtight container. They’ll keep well for up to 2 months. Thaw at room temperature to serve, and consider lightly warming for that bakery-fresh feel.

Reheating

While these cookies are delicious at room temperature, a quick zap in the microwave (about 10-15 seconds per cookie) revives the gooey caramel and makes them taste freshly baked. Keep a close eye so the brown sugar doesn’t get too runny. Serve warm for an extra indulgent treat!

FAQs

Can I use fresh pineapple instead of canned slices?

Absolutely! Just make sure to slice the fresh pineapple thin enough to fit into the pan cavities. Pat the slices dry with a paper towel so they don’t add extra moisture to the cookie dough.

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

No problem—muffin tins are a great alternative, and standard muffin cups fit pineapple rings perfectly. Grease them well and line the bottom with parchment rounds for easy removal.

Why is my brown sugar mixture leaking everywhere?

Some leakage is totally normal and creates a delectable caramel edge. Lining your cooling surface with wax or parchment paper helps with cleanup. If it’s excessive, try decreasing the butter slightly next time.

Can I make Pineapple Upside Down Sugar Cookies gluten-free?

Yes! Substitute your favorite 1:1 gluten-free flour blend for the all-purpose flour. Make sure all the other ingredients are gluten-free as well, and follow the recipe as written.

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

Greasing your pan well and spreading the brown sugar mixture evenly at the bottom usually does the trick. If anything still sticks, gently loosen with a thin spatula or butter knife while the cookies are still warm and reposition the toppings.

Final Thoughts

I can’t wait for you to experience the sunshine and happiness baked into every Pineapple Upside Down Sugar Cookie. Whether you make them for a festive gathering, a casual afternoon treat, or just because you’re craving something truly special, they’re guaranteed to become a new favorite. Bake a batch, share a few, and prepare for a rush of “Wow, you MADE these?!” moments. Enjoy every sweet, tropical bite!

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