Pineapple Upside-Down Sugar Cookies

If you’re looking for a delightful treat that combines nostalgia with an exciting twist, these Pineapple Upside-Down Sugar Cookies are just the ticket! Imagine sinking your teeth into a soft, chewy cookie topped with caramelized pineapple and a sweet cherry. It’s like bringing the classic upside-down cake to cookie form! This recipe is not only delicious, but it’s also perfect for family gatherings, potlucks, or even just a cozy evening at home.

One of the reasons I adore this recipe is its versatility. You can whip it up on a busy weeknight or impress your guests at a weekend gathering. The combination of buttery sugar cookies and tropical fruit creates a flavor explosion that everyone will love!

Why You’ll Love This Recipe

• Easy to make: This recipe comes together quickly and doesn’t require any fancy techniques.
• Family-friendly: Kids and adults alike will enjoy these sweet treats—perfect for all ages!
• Make-ahead convenience: Bake them in advance and enjoy them fresh whenever you like.
• Deliciously unique: The caramelized pineapple topping adds an unexpected twist that elevates your cookie game.

Ingredients You’ll Need

You won’t need anything fancy for these cookies—just simple, wholesome ingredients that you probably already have in your kitchen! Let’s gather everything together for our delicious Pineapple Upside-Down Sugar Cookies:

For the Topping:

• 1/2 cup unsalted butter, melted
• 1/2 cup brown sugar, packed
• 1 can (20 oz) pineapple slices, drained and cut into small pieces
• Maraschino cherries, halved

For the Sugar Cookies:

• 1 cup unsalted butter, softened
• 1 cup granulated sugar
• 1 large egg
• 1 tsp vanilla extract
• 2 1/2 cups all-purpose flour
• 1 tsp baking powder
• 1/4 tsp salt

Variations

One of the best things about this recipe is how flexible it can be! Feel free to get creative with these fun variations:

• Add nuts: Sprinkle some chopped pecans or walnuts on top for added crunch.
• Mix in spices: Try adding a pinch of cinnamon or nutmeg to the sugar cookie dough for extra warmth.
• Use different fruits: Swap out pineapple for peaches or strawberries to create your own fruity twist!
• Make mini cookies: Use a mini muffin tin to create bite-sized versions perfect for sharing.

How to Make Pineapple Upside-Down Sugar Cookies

Step 1: Prepare the Topping

Preheat your oven to 350°F (175°C) and lightly grease or line a muffin tin with parchment rounds. This step is crucial as it ensures that your cookies come out easily after baking. In a small bowl, mix the melted butter and brown sugar until well combined. Spoon about 1 tablespoon of this mixture into each muffin cup. The brown sugar will create that delicious caramel layer we all love!

Step 2: Add Pineapple and Cherries

Place a few small pieces of pineapple on top of the brown sugar mixture in each muffin cup. Then, press half of a maraschino cherry right in the center. These toppings not only add flavor but also make each cookie visually appealing!

Step 3: Make the Sugar Cookie Dough

In a large bowl, cream together the softened butter and granulated sugar until light and fluffy. This process incorporates air into your mixture, leading to soft cookies. Beat in the egg and vanilla extract until combined. In another bowl, whisk together flour, baking powder, and salt. Gradually add this dry mix to your wet ingredients until you form a soft dough.

Step 4: Assemble the Cookies

Take about 1 1/2 tablespoons of cookie dough and gently press it over the pineapple and cherry topping in each muffin cup. Flatten it slightly so that it covers everything evenly. This layering is key to ensuring every bite has that wonderful tropical flavor!

Step 5: Bake

Bake the cookies for 12-15 minutes or until the edges are lightly golden. Keep an eye on them—the smell will be heavenly! Remove them from the oven when ready.

Step 6: Cool and Serve

Let those lovely cookies cool in the muffin tin for about 5 minutes before carefully flipping it over onto a parchment-lined surface or cooling rack. Serve your Pineapple Upside-Down Sugar Cookies warm or at room temperature, enjoying each bite filled with caramelized goodness!

With this recipe, you’re sure to create something special that brings smiles all around!

Pro Tips for Making Pineapple Upside-Down Sugar Cookies

Baking these delightful cookies is a breeze, and with a few handy tips, you can ensure they turn out perfectly every time!

• Use room temperature ingredients: This helps create a smoother dough and better texture in your cookies. Cold butter or eggs can lead to uneven mixing, so letting them sit out for about 30 minutes before starting makes a big difference.

• Don’t overmix the dough: Mixing just until combined keeps your cookies soft and chewy. Overmixing can incorporate too much air and result in a tougher texture.

• Chill the cookie dough: If you have the time, chilling the dough for 30 minutes before baking can enhance the flavors and help prevent spreading during baking.

• Keep an eye on baking time: Every oven is different! Start checking your cookies around the 12-minute mark to avoid overbaking. You want them lightly golden on the edges but still soft in the center.

• Let them cool properly: Allowing your cookies to cool in the muffin tin for a few minutes before flipping helps maintain their shape. This also allows for the caramelized topping to set slightly, making for easier serving.

How to Serve Pineapple Upside-Down Sugar Cookies

These scrumptious cookies are perfect for sharing, whether at a gathering or as a sweet treat at home. Here are some ideas to elevate your presentation and enjoyment!

Garnishes

• Whipped coconut cream: A dollop of whipped coconut cream adds a rich, creamy contrast that complements the fruitiness of the cookies beautifully.
• Toasted coconut flakes: Sprinkle some toasted coconut on top for an added crunch and tropical flair that enhances the overall flavor.
• Mint leaves: A few fresh mint leaves not only add color but also provide a refreshing note that balances out the sweetness of the cookies.

Side Dishes

• Fresh fruit salad: A vibrant mix of seasonal fruits provides a refreshing counterpoint to the sweetness of the cookies. Try including pineapple, berries, and citrus for a colorful medley.
• Vanilla non-dairy ice cream: Serving these cookies warm alongside a scoop of vanilla non-dairy ice cream creates an indulgent dessert experience that’s hard to resist.
• Coconut milk smoothie: Blend up a quick smoothie with coconut milk and your favorite fruits for a light and refreshing drink that pairs wonderfully with these cookies.
• Herbal tea: A warm cup of herbal tea can be a delightful accompaniment, offering soothing flavors that complement the sweetness of your dessert without overwhelming it.

Enjoy creating these Pineapple Upside-Down Sugar Cookies! They’re sure to be a hit whether you’re baking for yourself or sharing with friends and family. Happy baking!

Make Ahead and Storage

These Pineapple Upside-Down Sugar Cookies are fantastic for meal prep! You can easily make them ahead of time, ensuring you have a delightful treat ready whenever the craving strikes.

Storing Leftovers

• Store any leftover cookies in an airtight container at room temperature for up to 3 days.
• If you want to keep them fresh longer, place parchment paper between layers of cookies to prevent them from sticking together.

Freezing

• Allow the cookies to cool completely before freezing.
• Place the cookies in a single layer on a baking sheet and freeze until solid.
• Once frozen, transfer them to a freezer-safe bag or container. They can be stored in the freezer for up to 3 months.

Reheating

• To enjoy warm cookies, preheat your oven to 350°F (175°C).
• Place the desired number of cookies on a baking sheet and heat for about 5-7 minutes until warmed through.
• Alternatively, you can microwave them for about 10-15 seconds for a quick warm-up.

FAQs

Here are some common questions about making Pineapple Upside-Down Sugar Cookies.

Can I use fresh pineapple instead of canned?

Yes, you can use fresh pineapple! Just make sure to cut it into small pieces similar in size to canned pineapple. This will help achieve even caramelization.

How do I store Pineapple Upside-Down Sugar Cookies?

Store your Pineapple Upside-Down Sugar Cookies in an airtight container at room temperature for up to 3 days or freeze them for longer storage.

Can I make these cookies gluten-free?

Absolutely! Substitute the all-purpose flour with a gluten-free flour blend that measures cup-for-cup. Just ensure other ingredients are also gluten-free.

Are Pineapple Upside-Down Sugar Cookies difficult to make?

Not at all! These cookies are quite simple and come together quickly. With just a few steps, you’ll have delicious treats that impress everyone!

Final Thoughts

I hope this recipe brings as much joy to your kitchen as it does to mine! These Pineapple Upside-Down Sugar Cookies are not just a dessert; they’re little bites of sunshine that brighten your day. Enjoy making them for yourself or sharing them with loved ones—either way, they’re sure to be a hit. Happy baking!