Pineapple Upside Down Sugar Cookies Recipe

If you haven’t yet discovered the magic of the Pineapple Upside Down Sugar Cookies Recipe, you are in for a real treat. This delightful fusion of classic pineapple upside down cake elements and the soft charm of sugar cookies brings sunshine and nostalgia into every bite. With juicy pineapple slices and bright maraschino cherries perfectly caramelized beneath a sweet, buttery cookie, these treats are not only visually stunning but a joyful twist on a beloved dessert. Whether you’re baking for a party, a family gathering, or simply to brighten your day, this recipe is sure to become a fast favorite.

Ingredients You’ll Need

Getting the ingredients right is the first step to cookie perfection. Each one plays a vital role, creating that lovely balance of texture, sweetness, and tropical flavor that make these cookies unforgettable.

• 1 cup butter (room temperature): Provides richness and a tender crumb for your cookies.
• 1 1/2 cups granulated sugar: Sweetens and helps create a light, fluffy batter.
• 2 eggs: Bind the dough and contribute to a soft texture.
• 2 tsp. vanilla extract: Adds warm, aromatic notes that complement the pineapple beautifully.
• 1/2 cup sour cream: Keeps cookies moist while adding subtle tanginess.
• 3 cups all-purpose flour: The base of your dough for that perfect cookie structure.
• 1 tsp. baking powder: A gentle leavening agent for just the right rise.
• 1 tsp. cornstarch: Helps create a tender, crumbly texture.
• 1/2 tsp. salt: Balances sweetness and enhances all other flavors.
• 13 canned pineapple slices: The star of the show, providing that iconic tropical flavor.
• 13 maraschino cherries: Add vibrant color and a sweet, fruity pop.
• 1/2 cup butter (melted): Used for caramelizing the brown sugar and pineapple.
• 1 cup light brown sugar (packed): Creates the luscious caramel layer that defines an upside down treat.

How to Make Pineapple Upside Down Sugar Cookies Recipe

Step 1: Prepare Your Pan and Oven

Start by preheating your oven to 350 degrees Fahrenheit. Meanwhile, get your USA pan mini round cake pan ready—this specialized pan is perfect for shaping the cookies with their signature topping. Preparing your tools sets the stage for smooth baking.

Step 2: Cream Butter and Sugar

In a large mixing bowl, combine the room temperature butter and granulated sugar, beating them together until light and fluffy. This crucial step creates the ideal texture for your cookies by incorporating air into the mixture.

Step 3: Add the Wet Ingredients

Next, beat in the eggs, vanilla extract, and sour cream until fully incorporated. The sour cream keeps the cookies tender and moist, while the eggs help bind everything together perfectly.

Step 4: Combine the Dry Ingredients

Mix the flour, baking powder, cornstarch, and salt in a separate bowl then gradually add to your wet mixture. Stir just until the dough comes together—you want it uniform but not overworked to maintain a tender crumb.

Step 5: Make the Caramel Base

In another bowl, stir together the melted butter and brown sugar until beautifully combined. This caramel mixture will form the sweet, sticky base that makes these cookies unforgettable.

Step 6: Layer the Pan with Caramel

Add about a tablespoon of the brown sugar mixture to the bottom of each cavity in your pan. Spread it evenly—it’s the canvas for your pineapple topping.

Step 7: Add Pineapple and Cherry Toppings

Place a pineapple slice on top of the caramel and nestle a maraschino cherry right in the center of the pineapple. This classic combo adds both visual appeal and a burst of bright flavor.

Step 8: Add the Cookie Dough Layer

Use a 3-tablespoon cookie scoop to add dough onto each pineapple slice. Flatten gently with an offset spatula so the dough covers the pineapple evenly and bakes uniformly.

Step 9: Bake to Perfection

Pop the pan into the oven and bake for 25 minutes, or until the edges turn golden brown and the caramel begins to bubble up around the sides. That bubbling sugar is your signal that the magic is happening!

Step 10: Cool and Release

Allow the cookies to cool for about 10 minutes, then carefully turn them out onto wax paper to catch the running caramel. If a pineapple slice sticks, just gently reposition it—every cookie deserves its perfect presentation.

Step 11: Final Cool Before Enjoying

Let the cookies cool completely to set their structure and flavors. Store extras in an airtight container to keep them fresh; they’re best enjoyed within 2 to 3 days for optimal taste.

How to Serve Pineapple Upside Down Sugar Cookies Recipe

Garnishes

Adding a light dusting of powdered sugar or a small swirl of whipped cream enhances the sweetness without overpowering the pineapple’s tang. A sprinkle of toasted coconut flakes can lend an exotic touch that pairs beautifully.

Side Dishes

Pair these cookies with a bright tropical fruit salad or a scoop of vanilla bean ice cream to create a delightful dessert plate. For beverages, a chilled glass of sparkling pineapple juice or a light iced tea complements the flavors gracefully.

Creative Ways to Present

Serve these cookies on a large rustic wooden board surrounded by fresh pineapple chunks and cherry stems for a charming display. For parties, arrange them on tiered stands so guests can admire their golden tops and caramel glimmer from every angle.

Make Ahead and Storage

Storing Leftovers

Keep your Pineapple Upside Down Sugar Cookies Recipe fresh by storing them in an airtight container at room temperature. They maintain their delightful texture for 2 to 3 days. Avoid stacking them too tightly to prevent sticking and preserve those gorgeous caramelized tops.

Freezing

If you want to save some for later, freeze the cookies individually on a baking sheet until firm, then transfer to a freezer-safe container. Thaw at room temperature when ready to enjoy. This way, you can have a tropical treat anytime you crave!

Reheating

Warm the cookies gently in a low oven (around 300 degrees Fahrenheit) for a few minutes or in the microwave for 10-15 seconds to revive their softness and caramel glow. Just be careful not to overheat and dry them out.

FAQs

Can I use fresh pineapple instead of canned?

Yes, fresh pineapple slices can be used but make sure they are cut into even, thin slices and patted dry to avoid excess moisture, which could affect the cookie texture.

What if I don’t have an offset spatula?

A butter knife or the back of a spoon works just fine to flatten the cookie dough over the pineapple; just be gentle and patient to keep the shape intact.

Is it possible to make these cookies gluten-free?

Absolutely! Substitute the all-purpose flour with a gluten-free flour blend designed for baking to keep the texture just right.

Can I double the recipe?

Yes, doubling the ingredients works well if you have a large enough pan or multiple pans. Just watch the baking time closely, as thicker batches may need a few extra minutes.

Why is there cornstarch in the recipe?

Cornstarch helps create a tender, soft crumb by limiting gluten development in the flour, making these cookies wonderfully delicate and melt-in-your-mouth.

Final Thoughts

From the first bite to the last crumb, the Pineapple Upside Down Sugar Cookies Recipe offers a vibrant twist on a beloved classic that’s hard not to love. They’re easy to make, visually stunning, and full of tropical flavor that brings pure joy to your kitchen creations. Go ahead, give them a try—once you do, they might just become your new go-to cookie for every occasion.

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