Pineapple Upside-Down Sugar Cookies

If you’re looking for a unique and delightful treat to impress your friends and family, these Pineapple Upside-Down Sugar Cookies are just the ticket! This recipe combines the classic flavors of pineapple upside-down cake with the charming texture of a sugar cookie. It’s a sweet twist that brings joy to every gathering, whether it’s a busy weeknight or a festive celebration. The combination of soft, chewy cookies topped with caramelized pineapple and cherries is simply irresistible!

These cookies hold a special place in my heart because they remind me of sunny days and family cookouts. Every bite is filled with nostalgia and happiness, making them perfect for sharing or enjoying on your own!

Why You’ll Love This Recipe

• Quick and Easy: These cookies come together in just 32 minutes, making them perfect for last-minute baking.
• Crowd-Pleaser: With their fruity topping and chewy texture, everyone will be asking for seconds!
• Versatile Treat: Great for any occasion—birthdays, holidays, or just a cozy night at home.
• Make-Ahead Friendly: You can prepare the dough in advance and bake them fresh when you’re ready to indulge.

Ingredients You’ll Need

Let’s gather some simple, wholesome ingredients to create these delightful Pineapple Upside-Down Sugar Cookies. You might already have many of these items in your pantry!

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 wonderfully flexible, allowing you to make it your own! Here are some fun variations to try:

• Add nuts: Chopped pecans or walnuts can add a delightful crunch.
• Switch up the fruit: Use diced peaches or mangoes instead of pineapple for a tropical twist.
• Experiment with spices: A pinch of cinnamon can warm up the flavor profile beautifully.
• Try different extracts: Almond extract could give a lovely depth that complements the fruit.

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 ensures that your cookies will easily release from the pan without sticking. In a small bowl, mix together the melted butter and brown sugar until fully combined. Spoon about 1 tablespoon of this mixture into each muffin cup. This creates a sweet base that will caramelize beautifully while baking!

Step 2: Add Fruit

Next, 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 into the center of each pineapple piece. This not only adds color but also enhances the flavor as they meld together during baking.

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, making for tender cookies. Beat in the egg and vanilla extract until everything is well combined.

Step 4: Combine Dry Ingredients

In another bowl, whisk together the flour, baking powder, and salt. Gradually add these dry ingredients to your wet mixture, mixing until you form a soft dough. It’s important not to overmix here; just blend until everything comes together nicely.

Step 5: 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 it covers everything evenly. This step helps ensure that every bite has that delicious topping underneath.

Step 6: Bake

Now it’s time to bake! Pop those trays into your preheated oven for about 12-15 minutes or until you see that lovely golden edge forming on your cookies. Baking time may vary slightly based on your oven, so keep an eye on them!

Step 7: Cool and Serve

Once baked, let your cookies cool in the muffin tin for about five minutes before carefully flipping them over onto a parchment-lined surface or cooling rack. Serving them warm or at room temperature allows everyone to enjoy that luscious caramelized topping paired perfectly with soft cookie goodness!

Now you’re ready to savor these delightful Pineapple Upside-Down Sugar Cookies! Enjoy!

Pro Tips for Making Pineapple Upside-Down Sugar Cookies

Baking is a delightful journey, and these tips will ensure your Pineapple Upside-Down Sugar Cookies turn out perfectly every time!

• Use room temperature ingredients: Starting with softened butter and room temperature eggs helps the dough mix together smoothly, resulting in a tender cookie texture.

• Don’t skip the chilling step: If you have time, chill the cookie dough for about 30 minutes before baking. This helps prevent spreading and allows the flavors to meld beautifully.

• Be precise with measurements: Baking is a science! Using the correct amount of each ingredient ensures your cookies rise properly and achieve that perfect chewy consistency.

• Watch your baking time closely: Ovens can vary widely in temperature. Start checking your cookies a minute or two before the suggested bake time to avoid overbaking.

• Experiment with add-ins: Feel free to customize your cookies! Adding chopped nuts or coconut flakes can give an extra crunch and enhance the tropical flavor profile.

How to Serve Pineapple Upside-Down Sugar Cookies

These delightful cookies are not only delicious but also visually appealing, making them perfect for any occasion. Here are some fun ways to serve them!

Garnishes

• Shredded coconut: A sprinkle of shredded coconut on top adds a delightful texture and enhances that tropical vibe.
• Whipped coconut cream: Serve with a dollop of whipped coconut cream for a creamy contrast to the chewy cookie.

Side Dishes

• Fresh fruit salad: A refreshing medley of seasonal fruits balances the sweetness of the cookies and adds a vibrant touch to your dessert table.
• Vanilla non-dairy ice cream: The creamy richness of vanilla non-dairy ice cream pairs wonderfully with the warm cookies, creating a comforting dessert experience.
• Herbal tea: A warm cup of herbal tea complements the tropical flavors beautifully while providing a soothing finish to your meal.
• Tropical smoothie: Blend up some banana, mango, and coconut milk for a refreshing drink that echoes the fruity notes in your cookies.

Enjoy crafting these delightful Pineapple Upside-Down Sugar Cookies and serving them with these creative ideas!

Make Ahead and Storage

These Pineapple Upside-Down Sugar Cookies are perfect for meal prep! You can easily make them ahead of time and store or freeze them for later enjoyment.

Storing Leftovers

• Allow the cookies to cool completely before storing.
• Place the cookies in an airtight container at room temperature.
• They are best enjoyed within 3-5 days but can last up to a week.

Freezing

• Bake and cool the cookies completely.
• Place them in a single layer on a baking sheet and freeze until solid.
• Once frozen, transfer the cookies to a freezer-safe bag or container, separating layers with parchment paper.
• They can be frozen for up to three months.

Reheating

• For best results, reheat in an oven preheated to 350°F (175°C) for about 5 minutes until warm.
• Alternatively, you can microwave individual cookies for about 10-15 seconds.

FAQs

If you have questions, we’ve got answers!

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

Absolutely! Just make sure to chop fresh pineapple into small pieces and drain any excess juice before using it as a topping.

How do I ensure my Pineapple Upside-Down Sugar Cookies turn out chewy?

To keep your cookies chewy, avoid overmixing the dough and don’t overbake. Keep an eye on them in the oven; they should be light golden around the edges when done.

Can I substitute ingredients in the Pineapple Upside-Down Sugar Cookies recipe?

Yes! You can replace unsalted butter with coconut oil or vegan butter if desired. Just ensure that all substitutes align with your dietary preferences.

Final Thoughts

I hope you find joy in making these delightful Pineapple Upside-Down Sugar Cookies! They’re not just a treat; they’re a way to bring a little sunshine into your day. Enjoy every bite of that sweet pineapple topping with your loved ones—happy baking!