Pineapple Upside Down Sugar Cookies Recipe

“`html

If you adore the classic charm of pineapple upside down cake but want a playful new twist, then you are going to fall head over heels for this Pineapple Upside Down Sugar Cookies Recipe. These delightful treats combine the buttery, tender texture of sugar cookies with the caramelized sweetness of brown sugar, juicy pineapple slices, and bright maraschino cherries perched on top. Every bite delivers a little tropical sunshine and a satisfying crunch of golden edges that will have you reaching for just one more. It’s a perfect way to enjoy the nostalgic flavors of pineapple upside down cake but in a fun, portable cookie form that’s ideal for sharing or savoring all by yourself.

Ingredients You’ll Need

This Pineapple Upside Down Sugar Cookies Recipe relies on simple, pantry-friendly ingredients that all play a crucial role in creating those perfect textures and rich flavors. Each component, from the creamy butter to the tangy sour cream and the fluffy flour blend, works harmoniously to give you cookies that are soft yet sturdy enough to hold their fruity toppings in place.

• Unsalted butter, 1 cup at room temperature: This adds richness and creates a tender, melt-in-your-mouth crumb.
• Granulated sugar, 1 1/2 cups: Essential for sweetness and to help with that delightful cookie browning.
• Large eggs, 2: Bind everything together while contributing to the cookie’s structure.
• Vanilla extract, 2 teaspoons: Gives a warm, aromatic depth that enhances every other ingredient.
• Sour cream, 1/2 cup: Adds moisture and tenderness, giving the cookie a slight tang and soft chew.
• All-purpose flour, 3 cups: The base that builds the cookie’s soft but sturdy framework.
• Baking powder, 1 teaspoon: Provides lift, keeping the cookies light and airy.
• Cornstarch, 1 teaspoon: Keeps the texture delicate and tender.
• Salt, 1/2 teaspoon: Balances the sweetness and brings out flavor complexity.
• Pineapple slices, 13 canned and drained: The star of the show offering juicy, tropical brightness.
• Maraschino cherries, 13: Pops of color and a classic pineapple upside down cookie touch.
• Melted unsalted butter, 1/2 cup: Mixed with brown sugar to create that irresistible caramel glaze.
• Light brown sugar, 1 cup packed: Creates a deep, molasses-rich caramel flavor for the topping.

How to Make Pineapple Upside Down Sugar Cookies Recipe

Step 1: Prep Your Oven and Pan

Start by preheating your oven to 350 degrees Fahrenheit (175 degrees Celsius). Grease your mini round cake pan or muffin tin thoroughly. This ensures the sticky caramel and juicy pineapple slices won’t cling and that your cookies pop out easily after baking.

Step 2: Cream Butter and Sugar

In a large mixing bowl, use an electric mixer to cream together the room temperature butter and granulated sugar until the mixture looks light, fluffy, and pale. This step is key to incorporating air that will give your cookies their tender crumb and slightly crisp edges.

Step 3: Add the Eggs, Vanilla, and Sour Cream

Beat the eggs, vanilla extract, and sour cream into the butter-sugar mixture until everything is smoothly combined. The sour cream adds moisture and a subtle tang that perfectly offsets the sweetness from the sugar and pineapple.

Step 4: Combine Dry Ingredients

In a separate bowl, whisk together the all-purpose flour, baking powder, cornstarch, and salt. This blend helps maintain a soft texture while providing the structure the cookies need.

Step 5: Mix Dry and Wet Ingredients

Gradually fold the dry ingredients into the wet mixture. Mix just until combined to avoid overworking the dough, which keeps your cookies tender rather than dense and chewy.

Step 6: Prepare the Brown Sugar Glaze

Blend the melted butter and light brown sugar until smooth and well combined. This glaze is what transforms the cookies into an irresistible pineapple upside down treat by creating a caramelized, sticky base underneath the fruit.

Step 7: Layer the Glaze and Fruit

Spoon about one tablespoon of the brown sugar glaze into each cavity of your prepared pan. Spread it evenly, then place a pineapple slice on top of the glaze. Nestle a maraschino cherry in the center of each pineapple ring for that perfect classic look.

Step 8: Add the Cookie Dough

Use a 3-tablespoon scoop to portion your cookie dough over each fruit-topped cup in the pan. Gently flatten each mound with an offset spatula to encourage even baking and nice coverage.

Step 9: Bake Until Golden

Bake your cookies for 25 minutes until they turn golden around the edges and you see the brown sugar bubbling up the sides. This signals that your caramel glaze is perfectly caramelized.

Step 10: Cool and Invert

Allow the cookies to cool for 10 minutes in the pan, then carefully invert them onto wax paper. This step lets the caramelized brown sugar glaze run lovingly over the cookie tops, creating that signature pineapple upside down look and flavor.

Step 11: Cool Completely Before Serving

Let your cookies cool fully before enjoying. This final chill sets the caramel topping and ensures each bite offers that perfect balance between soft cookie and sticky sweetness.

How to Serve Pineapple Upside Down Sugar Cookies Recipe

Garnishes

While these cookies are stunning as is, you can elevate their presentation with a light dusting of powdered sugar for a snowy touch or a small sprig of fresh mint to add a pop of green and fresh aroma. The delicate contrast of cool mint complements the warm caramel and vibrant pineapple beautifully.

Side Dishes

These cookies pair wonderfully with a scoop of vanilla bean ice cream or a dollop of whipped cream to balance their sweet, fruity richness. A hot cup of tea or freshly brewed coffee also makes an excellent accompaniment for an afternoon treat or delightful dessert.

Creative Ways to Present

Try serving these cookies on a tropical-themed platter adorned with pineapple leaves, coconut flakes, or edible flowers to instantly transport your guests to a sunny beachside. Alternatively, stack them as mini cookie towers tied with a ribbon for a charming gift or party favor.

Make Ahead and Storage

Storing Leftovers

Store your Pineapple Upside Down Sugar Cookies in an airtight container at room temperature for up to five days. This keeps them fresh and moist while maintaining that delicious soft texture and sticky glaze on top.

Freezing

If you want to save some for later, freeze the cooled cookies in a single layer on a baking sheet before transferring them to a freezer-safe container or zip-top bag. They freeze well for up to three months and thaw beautifully without losing their flavor or texture.

Reheating

When you’re ready to enjoy frozen cookies, let them thaw at room temperature, then warm gently in a low oven (around 300 degrees Fahrenheit) for 5-7 minutes to bring back their fresh-baked magic and make the caramel topping slightly melty again.

FAQs

Can I use fresh pineapple instead of canned for the Pineapple Upside Down Sugar Cookies Recipe?

You certainly can, but make sure to cut fresh pineapple slices to a similar size and drain any excess juice well to avoid soggy cookies. Fresh pineapple will add a brighter, more natural flavor, though canned is easier for consistent results.

What can I substitute for sour cream in this recipe?

If you don’t have sour cream on hand, plain Greek yogurt works wonderfully as a substitute. It provides the same tang and moisture while maintaining the cookie’s tender texture.

How do I prevent the cookies from sticking to the pan when inverting?

Grease your pan really well before adding the brown sugar glaze and fruit. You can also line the pan with parchment rounds cut to size for an extra non-stick layer, making flipping easier and cleaner.

Can I make these cookies gluten-free?

Yes! Swap the all-purpose flour for a gluten-free baking flour blend that includes xanthan gum. The result will be just as tasty and perfect for those with gluten sensitivities.

Why does the brown sugar glaze bubble up around the cookie edges?

That bubbling is the molten caramel forming as the sugar melts and interacts with the butter during baking. It’s exactly what you want—it’s the hallmark of that luscious pineapple upside down flavor and texture!

Final Thoughts

This Pineapple Upside Down Sugar Cookies Recipe is truly one of those special finds that combine the best of two beloved desserts in one bite-friendly form. Whether you’re baking for a celebration, a tropical-themed party, or just because you crave something sweet and nostalgic, these cookies will brighten your day and delight everyone lucky enough to try them. Give it a whirl and watch how quickly these gems disappear—you might just want to keep them all for yourself!

“`

Print