Pineapple Upside-Down Sugar Cookies

If you’re looking for a delightful treat that brings sunshine to your day, these Pineapple Upside-Down Sugar Cookies are just the ticket! Imagine soft and chewy cookies topped with sweet caramelized pineapple and bright maraschino cherries. This recipe is a true crowd-pleaser, perfect for busy weeknights or family gatherings where everyone craves something special. Each bite feels like a little slice of paradise!

These cookies not only taste amazing, but they also fill your kitchen with the most wonderful aroma as they bake. Whether you’re enjoying them with a cup of coffee or sharing them with friends, they’re sure to bring smiles all around.

Why You’ll Love This Recipe

• Easy to Make: With simple steps and common ingredients, you can whip these up in no time!
• Family-Friendly: Kids love the fun look and delicious taste of these cookies.
• Versatile: Perfect for parties, holidays, or a sweet snack anytime!
• Make-Ahead Convenience: Bake a batch ahead of time and enjoy them fresh throughout the week.
• Deliciously Unique: The twist on classic sugar cookies makes every bite exciting!

Ingredients You’ll Need

Creating these Pineapple Upside-Down Sugar Cookies is a breeze thanks to some simple, wholesome ingredients. Here’s what you’ll 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 enough to suit different tastes! Here are some fun variations you might want to try:

• Add Nuts: Sprinkle in some chopped walnuts or pecans for extra crunch.
• Change the Fruit: Swap out pineapple for peaches or cherries if you’re feeling adventurous!
• Use Different Extracts: Experiment with almond extract instead of vanilla for a nutty twist.
• Make It Gluten-Free: Substitute all-purpose flour with a gluten-free blend to accommodate dietary needs.

How to Make Pineapple Upside-Down Sugar Cookies

Step 1: Prepare the Topping

First things first! 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 and don’t stick. 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 gooey layer creates that beautiful topping we all adore!

Step 2: Add the Pineapple and Cherries

Now it’s time to add some fruity goodness! 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 in the center. This step not only adds flavor but also makes for an eye-catching presentation!

Step 3: Make the Sugar Cookie Dough

In a large bowl, cream together the softened butter and granulated sugar until light and fluffy—this usually takes about 3 minutes. It’s crucial because this process incorporates air into your dough, making your cookies soft and tender. Next, 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. Adding dry ingredients separately helps prevent clumps from forming when mixed into your wet ingredients.

Step 5: Mix Everything Together

Gradually add the dry mixture to your butter mixture. Mix until just combined; you want your dough to be soft but not sticky. Over-mixing can lead to tough cookies, so gently fold everything together!

Step 6: Assemble the Cookies

Take about 1 ½ tablespoons of cookie dough and press it over the pineapple and cherry topping in each muffin cup. Gently flatten it so it covers the toppings evenly. This ensures that every bite has that delicious fruit topping!

Step 7: Bake Your Cookies

Pop your muffin tin in the oven and bake for about 12-15 minutes or until you see golden edges forming on top of your cookies. The anticipation will be worth it as they start smelling heavenly!

Step 8: Cool Before Serving

Let those scrumptious cookies cool in the muffin tin for about 5 minutes before flipping them onto a parchment-lined surface or cooling rack. This step allows them to set properly while still warm.

Step 9: Enjoy!

Now comes the best part—serving! Enjoy these warm or at room temperature. Each bite is filled with caramelized pineapple goodness atop that soft sugar cookie base!

Pro Tips for Making Pineapple Upside-Down Sugar Cookies

Baking should be fun and rewarding, so here are some tips to ensure your cookies turn out perfectly every time!

• Use room temperature ingredients: Start with softened butter and eggs at room temperature for better mixing, resulting in a smoother dough that bakes evenly.

• Don’t overmix the dough: Mixing just until the ingredients are combined helps maintain the cookies’ soft and chewy texture instead of making them tough.

• Press down gently: When flattening the cookie dough over the topping, be gentle. This ensures the pineapple and cherry toppings stay intact while baking.

• Cool before serving: Allowing the cookies to cool for a few minutes in the tin before flipping helps them set up nicely, preventing breakage and ensuring they hold their shape.

• Experiment with toppings: Feel free to mix things up by adding nuts or using different fruit combinations. This adds a personal touch and can create new flavor profiles!

How to Serve Pineapple Upside-Down Sugar Cookies

These delightful cookies not only taste amazing but also look lovely when presented. Here are a few ideas on how to serve them!

Garnishes

• Whipped coconut cream: A dollop of whipped coconut cream on top adds a light and creamy element that complements the sweet flavors beautifully.
• Toasted coconut flakes: Sprinkling toasted coconut over the cookies enhances their tropical vibe and adds a delightful crunch.

Side Dishes

• Fresh fruit salad: A colorful medley of seasonal fruits like berries, melons, and grapes provides a refreshing contrast to the rich cookies.
• Vanilla almond milk: Serving these cookies with cold vanilla almond milk makes for a delicious pairing that balances sweetness with nutty flavor.
• Coconut ice cream: The creamy texture of coconut ice cream alongside these warm cookies creates a delightful combination that’s perfect for dessert lovers.
• Herbal tea: A soothing cup of herbal tea, such as chamomile or peppermint, pairs wonderfully with these sweet treats, adding warmth and comfort to your snack time.

Enjoy creating and sharing your Pineapple Upside-Down Sugar Cookies! They’re sure to bring smiles all around.

Make Ahead and Storage

These Pineapple Upside-Down Sugar Cookies are not only a delightful treat but also perfect for meal prep! You can make them ahead of time and store them for later enjoyment.

Storing Leftovers

• Allow the cookies to cool completely before storing.
• Place them in an airtight container at room temperature for up to 3 days.
• For longer freshness, refrigerate them, where they can last up to a week.

Freezing

• To freeze, wrap individual cookies tightly in plastic wrap or aluminum foil.
• Place wrapped cookies in a freezer-safe bag or container.
• They can be frozen for up to 2 months. Just remember to label the container with the date!

Reheating

• To reheat, simply place the desired number of cookies on a baking sheet.
• Warm in a preheated oven at 350°F (175°C) for about 5-7 minutes until heated through.
• Enjoy warm for that freshly baked taste!

FAQs

Have questions about these delicious treats? Here are some common inquiries you might have.

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

Yes! You can absolutely use fresh pineapple. Just make sure to cut it into small pieces and follow the same instructions for caramelization.

How do I keep my Pineapple Upside-Down Sugar Cookies from getting soggy?

To prevent sogginess, ensure that your pineapple is well-drained before adding it to the cookie base. Additionally, store the cookies in an airtight container but avoid stacking them too high.

Can I make Pineapple Upside-Down Sugar Cookies gluten-free?

Definitely! Substitute all-purpose flour with a gluten-free flour blend that works well in baking.

How long will Pineapple Upside-Down Sugar Cookies last?

When stored properly, these cookies can last up to 3 days at room temperature or up to a week in the refrigerator.

Final Thoughts

I hope you find joy in making these Pineapple Upside-Down Sugar Cookies as much as I do! They’re not just delicious; they’re also a fun twist on a classic dessert. Whether you’re sharing them with friends or savoring them solo, I’m sure they’ll bring smiles all around. Enjoy your baking adventure!