Pineapple Upside-Down Sugar Cookies

If you’re looking for a delightful treat that brings a little sunshine to your day, these Pineapple Upside-Down Sugar Cookies are just what you need! Imagine soft, chewy cookies topped with caramelized pineapple and a hint of cherry sweetness. They’re perfect for family gatherings, cozy afternoons, or even just a sweet indulgence after a long day. This recipe is not only a crowd-pleaser but also super easy to whip up, making it a go-to in my kitchen!

What makes these cookies truly special is the beautiful combination of flavors and textures. The buttery sugar cookie base pairs perfectly with the tropical notes of pineapple and the pop of the cherry on top. Trust me, once you try this recipe, you’ll find yourself reaching for it time and again!

Why You’ll Love This Recipe

• Simple to Make: With straightforward steps and easy-to-find ingredients, anyone can bake these cookies!
• Family Favorite: Kids and adults alike love the sweet topping and soft cookie texture.
• Perfect for Any Occasion: Whether it’s a birthday party or just a cozy night in, these cookies fit right in.
• Make-Ahead Friendly: You can prepare the dough ahead of time and bake them fresh when needed!
• Deliciously Unique: The twist on classic sugar cookies makes them stand out from the crowd.

Ingredients You’ll Need

These Pineapple Upside-Down Sugar Cookies use simple, wholesome ingredients that you probably already have in your pantry. Let’s gather what we need!

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

This recipe is flexible, allowing you to get creative with flavors! Here are some fun variations you can try:

• Add Some Spice: Sprinkle in some cinnamon or nutmeg into the cookie dough for extra warmth.
• Switch Up the Fruit: Substitute strawberries or peaches for pineapple for a different fruity twist!
• Make It Coconutty: Add shredded coconut to both the topping and dough for a tropical vibe.
• Chocolate Drizzle: Finish with a drizzle of melted chocolate over the cooled cookies for an indulgent touch.

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. In a small bowl, mix together the melted butter and brown sugar until well combined. This mixture will create that delicious caramel layer at the bottom of each cookie. Spoon about 1 tablespoon into each muffin cup, then add small pieces of pineapple on top followed by pressing half of a maraschino cherry in each one. This step sets up your delightful topping!

Step 2: Make the Sugar Cookie Dough

In a large bowl, cream together the softened butter and granulated sugar until light and fluffy. This creates an airy base for your cookies! Beat in the egg and vanilla extract until everything is well mixed. In another bowl, whisk together flour, baking powder, and salt—this helps keep your cookies tender. Gradually combine the dry ingredients with the wet ingredients until you form a soft dough that’s ready to be pressed over those fruity toppings.

Step 3: Assemble the Cookies

Take about 1 1/2 tablespoons of cookie dough and gently press it over the pineapple-cherry topping in each muffin cup. Make sure to flatten it slightly so it evenly covers everything below. This ensures that each bite has that sweet topping bursting through!

Step 4: Bake

Bake those beauties in your preheated oven for about 12-15 minutes or until you see golden edges peeking out. The aroma of warm cookies will fill your kitchen—just wait until you take them out!

Step 5: Cool & Serve

Let the cookies cool in the muffin tin for about 5 minutes before carefully flipping them onto a parchment-lined surface or cooling rack. You want to let those caramelized toppings shine! Serve them warm or at room temperature, and enjoy every sweet bite of these Pineapple Upside-Down Sugar Cookies!

Pro Tips for Making Pineapple Upside-Down Sugar Cookies

Baking these delightful cookies can be a breeze with a few simple tips to ensure they turn out perfectly every time!

• Use Room Temperature Ingredients: Having your butter and egg at room temperature allows them to blend more easily, resulting in a smoother cookie dough and a better texture.

• Don’t Overmix the Dough: Gently mix the dry ingredients into the wet ones just until combined. Overmixing can lead to tough cookies instead of the soft and chewy texture we’re aiming for.

• Chill the Dough if Necessary: If your dough is too soft to handle, a quick chill in the fridge for about 30 minutes can firm it up, making it easier to press over the pineapple topping.

• Check Your Oven Temperature: Ovens can vary significantly in temperature. Use an oven thermometer to ensure yours is accurate, which helps achieve that perfect golden edge without burning.

• Experiment with Toppings: Don’t hesitate to get creative! Adding coconut flakes or chopped nuts on top of the cookie dough before baking can introduce new flavors and textures.

How to Serve Pineapple Upside-Down Sugar Cookies

These Pineapple Upside-Down Sugar Cookies are not only delicious but also visually appealing. Here are some fun ways to present them!

Garnishes

• Whipped Coconut Cream: A dollop of whipped coconut cream adds a light and tropical touch that complements the flavors beautifully.
• Toasted Coconut Flakes: Sprinkling toasted coconut on top gives an extra crunch and enhances the tropical vibe of these cookies.
• Fresh Mint Leaves: A sprig of fresh mint not only adds color but also provides a refreshing contrast to the sweetness of the cookies.

Side Dishes

• Tropical Fruit Salad: A mix of fresh fruits like mango, kiwi, and papaya will brighten up your meal and enhance those tropical flavors.
• Vanilla Ice Cream: The creamy richness of vanilla ice cream pairs wonderfully with these warm cookies, creating a delightful dessert experience.
• Coconut Milk Rice Pudding: This creamy side dish offers a comforting contrast and echoes the tropical notes of the cookies nicely.
• Lemonade or Iced Tea: A refreshing drink like homemade lemonade or iced tea will cleanse your palate while balancing the sweetness of the cookies.

With these serving suggestions and pro tips, you’re all set to impress friends and family with your Pineapple Upside-Down Sugar Cookies! Enjoy every bite!

Make Ahead and Storage

These Pineapple Upside-Down Sugar Cookies are perfect for meal prep, making them an excellent choice for gatherings or sweet cravings throughout the week. With a few simple storing methods, you can enjoy them fresh for days!

Storing Leftovers

• Store leftover cookies in an airtight container at room temperature for up to 3 days.
• If you’d like to maintain their freshness longer, consider refrigerating them for up to a week.

Freezing

• To freeze, allow the cookies to cool completely.
• Place them in a single layer on a baking sheet and freeze for about 1 hour until solid.
• Transfer the frozen cookies to a freezer-safe bag or container, layering parchment paper between them, and store for up to 3 months.

Reheating

• For the best taste and texture, reheat cookies in the oven at 350°F (175°C) for about 5-7 minutes until warmed through.
• Alternatively, you can use the microwave; heat each cookie on a microwave-safe plate for 10-15 seconds.

FAQs

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

Can I use fresh pineapple instead of canned?

Absolutely! Fresh pineapple will give a bright flavor, just be sure to cut it into small pieces similar in size to canned pineapple for even cooking.

How do I make Pineapple Upside-Down Sugar Cookies without eggs?

You can replace the egg with 1/4 cup of unsweetened applesauce or a flaxseed egg (1 tablespoon ground flaxseed mixed with 2.5 tablespoons water). Both alternatives work well in keeping the cookies moist!

What is the best way to enjoy Pineapple Upside-Down Sugar Cookies?

These cookies are delightful either warm or at room temperature! Pair them with a scoop of vanilla non-dairy ice cream for an extra special treat.

Can Pineapple Upside-Down Sugar Cookies be made gluten-free?

Yes! Simply substitute all-purpose flour with your favorite gluten-free flour blend. Adjusting may be necessary based on the specific blend used.

Final Thoughts

I hope you find joy in making these scrumptious Pineapple Upside-Down Sugar Cookies! They bring together delightful flavors that remind us of sunny days and sweet gatherings. Whether you’re baking for friends or treating yourself, these cookies are sure to impress. Enjoy every bite and share your creations with loved ones!