Pineapple Upside-Down Sugar Cookies

If you’re looking for a sweet treat that combines nostalgia with a tropical twist, these Pineapple Upside-Down Sugar Cookies are just the thing! I remember the first time I made them; the aroma of caramelized pineapple wafting through my kitchen brought back so many happy memories. These cookies are soft, chewy, and topped with a delightful layer of pineapple and cherry goodness. They are perfect for busy weeknights or family gatherings when you want to impress without spending hours in the kitchen.

These cookies have a way of bringing smiles to everyone’s faces, making them a favorite in my home. Plus, they’re easy to whip up and fun to share. Trust me, once you take that first bite, you’ll understand why they hold such a special place in my heart!

Why You’ll Love This Recipe

• Easy to make: With simple steps and accessible ingredients, even beginner bakers can nail this recipe.
• Family-friendly: Kids and adults alike will love the sweet, fruity topping and buttery cookie base.
• Perfect for sharing: Bring these cookies to gatherings or bake a batch for friends—they’re sure to be a hit!
• Make-ahead convenience: You can prepare the dough in advance and bake whenever you’re ready for something sweet.

Ingredients You’ll Need

This recipe calls for simple, wholesome ingredients that you likely already have in your pantry. Let’s gather what we need to create these 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 these cookies is how flexible they can be! Feel free to get creative with different toppings or cookie flavors.

• Try different fruits: Use peaches or strawberries instead of pineapple for a unique twist.
• Add spices: A dash of cinnamon or nutmeg in the cookie dough can add warmth and depth.
• Make it gluten-free: Substitute all-purpose flour with your favorite gluten-free blend.
• Switch up the sweetness: Use coconut sugar instead of brown sugar for a different flavor profile.

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 come out easily without sticking. 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—this will create that amazing caramel layer!

Step 2: Add Pineapple and Cherries

Now it’s time for the fun part! Place a few small pieces of pineapple on top of the brown sugar mixture in each muffin cup. Press half of a maraschino cherry in the center of each one. This pairing adds color and sweetness that makes these cookies truly special.

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, which is key for creating soft cookies. Beat in the egg and vanilla extract until everything is well combined.

Step 4: Combine Dry Ingredients

In another bowl, whisk together flour, baking powder, and salt. Gradually add this dry mixture to your wet ingredients, mixing until you have a soft dough. It’s important not to overmix at this stage—just combine until you see no dry flour left.

Step 5: Assemble the Cookies

Take about 1 1/2 tablespoons of cookie dough and press it over the pineapple and cherry topping in each muffin cup. Gently flatten it so it covers everything nicely. This helps ensure that every bite has that delicious topping underneath.

Step 6: Bake

Pop those beauties into your preheated oven! Bake them for about 12-15 minutes or until the edges turn lightly golden. Keep an eye on them; you want those edges just right!

Step 7: Cool & Serve

Let your cookies cool in the muffin tin for about 5 minutes before carefully flipping it onto a parchment-lined surface or cooling rack. This allows them to set perfectly while still being warm enough to enjoy right away!

Serve them warm or at room temperature—you’ll love how delightful they taste with that luscious caramelized topping paired with soft cookie bliss! Enjoy every bite!

Pro Tips for Making Pineapple Upside-Down Sugar Cookies

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

• Use room temperature butter: Softened butter mixes more thoroughly into the sugar, creating a lighter and fluffier cookie base.
• Don’t skip cooling: Allowing the cookies to cool in the muffin tin for a few minutes before flipping them helps maintain their shape and prevents sticking.
• Press toppings gently: Pressing the pineapple and cherry toppings lightly ensures they stay in place during baking and enhances that beautiful presentation.
• Experiment with fruit: Feel free to swap out the pineapple or cherries for other fruits like peaches or berries to create your own unique twist!
• Store properly: Keep leftover cookies in an airtight container at room temperature to maintain their soft texture for up to three days.

How to Serve Pineapple Upside-Down Sugar Cookies

Serving your Pineapple Upside-Down Sugar Cookies can elevate the experience. Whether it’s a casual gathering or a special occasion, these tips will help you present them beautifully.

Garnishes

• Shredded coconut: Sprinkle some toasted coconut on top for added flavor and texture, complementing the tropical vibe of the pineapple.
• Whipped topping: A dollop of coconut or non-dairy whipped topping adds creaminess that pairs wonderfully with the cookies’ sweetness.

Side Dishes

• Fresh fruit salad: A vibrant mix of seasonal fruits provides a refreshing contrast to the richness of the cookies.
• Vanilla ice cream: The creamy goodness of vanilla ice cream complements the warm cookies perfectly, creating a delicious dessert combination.
• Coconut milk smoothie: Blend coconut milk with bananas and a hint of vanilla for a tropical beverage that harmonizes with your cookies.
• Herb-infused tea: A light herbal tea, such as mint or chamomile, can balance the sweetness of the cookies while enhancing your overall dessert experience.

Now that you have all these serving ideas and tips, it’s time to share these Pineapple Upside-Down Sugar Cookies with friends and family. Enjoy!

Make Ahead and Storage

These Pineapple Upside-Down Sugar Cookies are perfect for meal prep, making them a delightful treat to have on hand for any occasion. Whether you want to enjoy them fresh or save some for later, here’s how to keep them at their best.

Storing Leftovers

• Allow the cookies to cool completely before storing.
• Place the cookies in an airtight container at room temperature.
• They will stay fresh for up to 3 days.

Freezing

• To freeze, let the cookies cool completely.
• Place them in a single layer on a baking sheet and freeze until solid.
• Transfer the frozen cookies to an airtight container or freezer bag, separating layers with parchment paper.
• They can be frozen for up to 2 months.

Reheating

• For best results, reheat cookies in the oven at 350°F (175°C) for about 5-7 minutes.
• Alternatively, use a microwave; heat each cookie for about 10-15 seconds until warm.

FAQs

If you have questions about these delicious cookies, you’re not alone! Here are some common inquiries that might help you out.

Can I make Pineapple Upside-Down Sugar Cookies without maraschino cherries?

Absolutely! If you prefer not to use maraschino cherries, you can simply omit them or substitute with another fruit like sliced strawberries or blueberries for a fruity twist.

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

To keep your sugar cookies soft, avoid overbaking them. Keep an eye on the edges; they should be lightly golden but not browned. Also, store them in an airtight container when cooled.

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

Yes, using fresh pineapple is a great option! Just make sure to cut it into small pieces and cook it slightly if you’d like to soften it before adding it to your cookies.

How long do Pineapple Upside-Down Sugar Cookies last?

When stored properly in an airtight container at room temperature, these cookies will stay fresh for about 3 days. If frozen, they can last up to 2 months!

Can I double the recipe for Pineapple Upside-Down Sugar Cookies?

Definitely! Doubling the recipe is a great idea if you’re planning a gathering or want extra treats. Just make sure you have enough muffin tins or bake in batches!

Final Thoughts

I hope this recipe brings as much joy to your kitchen as it has brought to mine! The combination of sweet caramelized pineapple and chewy sugar cookie is truly special. Enjoy making these delightful Pineapple Upside-Down Sugar Cookies and share them with friends and family. Happy baking!