Pineapple Upside Down Sugar Cookies Recipe

If you’re craving a delightful treat that combines fruity charm with classic sweetness, this Pineapple Upside Down Sugar Cookies Recipe will be your new best friend in the kitchen. Imagine a soft, tender sugar cookie infused with juicy crushed pineapple, crowned with a sticky brown sugar base and a vibrant maraschino cherry in the center — capturing all the nostalgic flavors of the traditional pineapple upside down cake in a fun, handheld form. These cookies are irresistibly moist with a beautiful golden sheen and a burst of tropical goodness in every bite, perfect for sharing or sneaking a few just for yourself.

Ingredients You’ll Need

The beauty of this Pineapple Upside Down Sugar Cookies Recipe lies in its simplicity, calling for everyday ingredients that come together to create something truly special. Each ingredient plays a crucial role, from the soft, tender crumb provided by the flour and butter to the sweet tanginess of pineapple and the caramel-like flavor from the brown sugar topping.

• 1 ½ cups all-purpose flour: The essential base for a soft and tender cookie texture.
• 1 teaspoon baking soda: Helps the cookies rise and spread just right.
• ½ teaspoon baking powder: Adds a lightness that keeps the cookies from being dense.
• ¼ teaspoon salt: Balances sweetness and enhances all other flavors.
• ¾ cup unsalted butter, softened: Contributes richness and moisture for that melt-in-your-mouth feel.
• 1 cup granulated sugar: Sweetens the dough, creating that classic sugar cookie flavor.
• 1 large egg: Binds everything together and adds a subtle richness.
• 1 teaspoon vanilla extract: Infuses the dough with a warm, inviting aroma and depth.
• ½ cup crushed pineapple (drained): Brings bright, tropical notes and moisture to each bite.
• ¼ cup brown sugar: For the caramel-like, sticky base layer under each cookie.
• 6 maraschino cherries, halved: Classic garnish adding color and a burst of sweet juiciness on top.
• Cooking spray or parchment paper: Prevents sticking and ensures perfect baking.

How to Make Pineapple Upside Down Sugar Cookies Recipe

Step 1: Prepare Your Oven and Baking Surface

Start by preheating your oven to 350°F (175°C). It’s key to get the oven hot and ready so the cookies bake evenly. Line a baking sheet with parchment paper or lightly spray it with cooking spray to prevent sticking. This step makes cleanup easier and keeps your cookies looking flawless.

Step 2: Mix the Dry Ingredients

In a medium bowl, whisk together the all-purpose flour, baking soda, baking powder, and salt. This ensures all your rising agents and seasoning are evenly distributed, setting the foundation for perfectly textured cookies.

Step 3: Cream the Butter and Sugar

In a large mixing bowl, cream the softened butter with granulated sugar until the mixture becomes light and fluffy, about 3 to 4 minutes. This process traps air, which helps make the cookies tender and gives them a lovely crumb.

Step 4: Add Egg and Vanilla

Beat in the egg and vanilla extract to your butter-sugar mixture until fully combined. The egg adds moisture and structure, while vanilla heightens the sweetness with its warm flavor.

Step 5: Combine Wet and Dry Ingredients

Gradually add the dry ingredients to the wet ingredients, mixing just until the dough comes together. Avoid overmixing so your cookies stay tender and don’t turn tough.

Step 6: Fold in Crushed Pineapple

Gently fold in the drained crushed pineapple, ensuring even distribution but being careful not to break up the pineapple too much. This juicy addition makes these cookies wonderfully moist and adds that signature tropical twist.

Step 7: Prepare the Brown Sugar Topping

Mix the brown sugar with a little melted butter if desired to create a sticky, caramel-like topping. Spread a spoonful of this mixture evenly onto your lined baking sheet in small mounds where each cookie will go.

Step 8: Shape the Cookies

Place a tablespoon of cookie dough over each brown sugar mound and gently flatten each mound slightly with your fingers. This helps the dough stick to the brown sugar and encourages a beautiful caramelized bottom.

Step 9: Add the Cherry Top

Press one half of a maraschino cherry into the center of each cookie. This not only adds a pop of color but also complements the pineapple with a burst of sweet juiciness.

Step 10: Bake to Perfection

Pop your cookies into the preheated oven and bake for 10 to 12 minutes, or until the edges are lightly golden. Watching for these visual cues ensures your cookies are perfectly baked, chewy in the middle with a slight crisp on the edges.

Step 11: Cool Before Serving

Once baked, allow the cookies to cool on the baking sheet for about 5 minutes to let them firm up a bit, then transfer them to a wire rack to finish cooling. Cooling makes them easier to handle and helps the caramel topping set nicely.

How to Serve Pineapple Upside Down Sugar Cookies Recipe

Garnishes

For an extra special presentation, sprinkle a little finely chopped fresh mint or a light dusting of powdered sugar over your cookies just before serving. Both add a hint of freshness and elevate the visual appeal beautifully alongside the vibrant cherry-top.

Side Dishes

Pair these cookies with a scoop of vanilla bean ice cream or a dollop of whipped cream for a delightful contrast between warm and cold. A tropical fruit salad or even a cup of lightly brewed green tea also complements the pineapple’s brightness and the cookies’ sweetness wonderfully.

Creative Ways to Present

Try arranging the Pineapple Upside Down Sugar Cookies Recipe on a rustic wooden board surrounded by fresh pineapple wedges and cherries for an eye-catching platter. Alternatively, serve them stacked with layers of lemon curd or cream cheese frosting for a decadent twist that’s sure to impress your guests.

Make Ahead and Storage

Storing Leftovers

Store any leftover cookies in an airtight container at room temperature for up to 3 days. Keeping them sealed helps retain their soft texture and prevents the pineapple from drying out, ensuring each cookie tastes just as good as fresh.

Freezing

If you want to keep these delicious Pineapple Upside Down Sugar Cookies Recipe longer, freeze them in a single layer on a baking sheet first, then transfer to a freezer bag or container. They can be frozen for up to 2 months and still maintain great flavor and texture.

Reheating

When ready to enjoy frozen cookies, thaw them at room temperature and warm slightly for about 5 to 7 minutes in a 300°F oven. This refreshes their softness and revives that wonderful caramelized topping, making them taste freshly baked again.

FAQs

Can I use fresh pineapple instead of canned crushed pineapple?

Absolutely! Just make sure to finely crush fresh pineapple and drain it well to avoid adding too much moisture, which can affect the cookie’s texture. Fresh pineapple can add an even brighter, more vibrant flavor to the cookies.

What if I don’t have maraschino cherries?

You can substitute maraschino cherries with glacé cherries, dried cherries, or even halved fresh cherries if they’re in season. Each will give a slightly different texture but still bring that sweet fruitiness that pairs perfectly with pineapple.

Can these cookies be made gluten-free?

Yes! Replace the all-purpose flour with a gluten-free baking blend that closely mimics regular flour. Be sure to check that all other ingredients are gluten-free to keep the cookies safe for those with gluten sensitivities.

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

Using parchment paper or a good coating of cooking spray is key. This Pineapple Upside Down Sugar Cookies Recipe has a sticky brown sugar base, so a non-stick layer on the baking sheet helps you remove cookies cleanly and preserves that beautiful caramel bottom.

Can I double the recipe for a larger batch?

Definitely! Just be sure to use multiple baking sheets and avoid overcrowding the cookies, which could affect baking time and evenness. Baking in batches ensures every cookie bakes perfectly with that classic golden edge.

Final Thoughts

This Pineapple Upside Down Sugar Cookies Recipe is a joyful spin on a beloved classic, bringing tropical warmth and a sweet, buttery bite to your cookie collection. Once you try these, they’ll quickly become your go-to for sharing with friends or indulging in a comforting moment all to yourself. So grab your ingredients, get baking, and savor the sunny deliciousness of these wonderful cookies!

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