Pineapple Upside-Down Sugar Cookies

Delight in these soft and chewy Pineapple Upside-Down Sugar Cookies, featuring a luscious caramelized pineapple and cherry topping over a buttery sugar cookie base. These cookies are perfect for gatherings or as a sweet treat anytime, combining the classic flavors of pineapple upside-down cake with the ease of sugar cookies.

Why You’ll Love This Recipe

• Irresistible Flavor: The combination of caramelized pineapple and cherries adds a unique sweetness that pairs perfectly with the buttery cookie base.
• Easy to Make: With simple ingredients and straightforward steps, these cookies come together quickly, making them perfect for baking novices.
• Versatile Treat: Enjoy them warm from the oven or at room temperature; they’re great for parties, picnics, or just because!
• Fun Presentation: These cookies are baked in muffin tins, giving them a delightful shape that’s sure to impress your friends and family.
• Family-Friendly Recipe: Kids will love helping out in the kitchen, especially when it comes to assembling the toppings!

Tools and Preparation

Before you dive into baking, gather your tools. Having everything ready will make the process smoother and more enjoyable.

Essential Tools and Equipment

• Muffin tin
• Mixing bowls
• Whisk
• Measuring cups and spoons
• Rubber spatula

Importance of Each Tool

• Muffin tin: This is essential for creating the unique shape of your Pineapple Upside-Down Sugar Cookies.
• Mixing bowls: You’ll need these for combining ingredients effectively without any mess.
• Whisk: A whisk helps incorporate air into your mixture for fluffier cookies.
• Rubber spatula: Perfect for scraping down the sides of bowls and folding ingredients together without overmixing.

Ingredients

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

How to Make Pineapple Upside-Down Sugar Cookies

Step 1: Preheat the Oven

Preheat your oven to 350°F (175°C) and lightly grease or line a muffin tin with parchment rounds.

Step 2: Prepare the Topping

In a small bowl, mix the melted butter and brown sugar until combined. Spoon about 1 tablespoon of this mixture into the bottom of each muffin cup. Place a few small pieces of pineapple on top of the brown sugar mixture, then press half of a maraschino cherry in the center of each one.

Step 3: Make the Sugar Cookie Dough

In a large bowl, cream together the softened butter and granulated sugar until light and fluffy. Beat in the egg and vanilla extract until well combined. In a separate bowl, whisk together the flour, baking powder, and salt. Gradually add the dry ingredients to the wet ingredients, mixing until a soft dough forms.

Step 4: 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 the dough so it evenly covers the topping.

Step 5: Bake

Bake the cookies for 12-15 minutes or until the edges are lightly golden.

Step 6: Cool Down

Let the cookies cool in the muffin tin for 5 minutes before carefully flipping the tin over onto a parchment-lined surface or cooling rack.

Step 7: Serve

Serve warm or at room temperature. Enjoy your delicious Pineapple Upside-Down Sugar Cookies with their delightful caramelized topping!

How to Serve Pineapple Upside-Down Sugar Cookies

Pineapple Upside-Down Sugar Cookies are a delightful treat that can be enjoyed in various ways. Whether you’re hosting a party or simply indulging yourself, here are some serving suggestions to elevate your cookie experience.

Pair with Ice Cream

• Vanilla ice cream: The creamy texture complements the chewy cookies wonderfully.
• Coconut sorbet: Adds a tropical twist that enhances the pineapple flavor.

Create a Cookie Sandwich

• Ice cream sandwich: Place a scoop of your favorite ice cream between two cookies for a fun dessert.
• Whipped cream filling: Spread whipped cream or coconut cream for a lighter option.

Serve with Fresh Fruit

• Sliced strawberries: Fresh berries add a burst of color and flavor to your dessert table.
• Citrus slices: Oranges or grapefruits provide a refreshing contrast to the sweetness.

Drizzle with Caramel Sauce

• Homemade caramel sauce: A warm drizzle can enhance the flavors and create an indulgent treat.
• Store-bought caramel sauce: For convenience, this is an easy way to add richness.

How to Perfect Pineapple Upside-Down Sugar Cookies

To ensure your Pineapple Upside-Down Sugar Cookies turn out perfectly every time, consider these helpful tips.

• Use room temperature ingredients: Ensure butter and egg are at room temperature for optimal mixing and texture.
• Don’t overmix the dough: Mixing just until combined will keep cookies soft and chewy.
• Chill the dough if needed: If the dough feels too sticky, refrigerating it for 30 minutes can help shape it better.
• Watch baking time closely: Keep an eye on your cookies as they bake; remove them when edges are lightly golden to avoid overbaking.
• Store properly: Keep cookies in an airtight container to maintain freshness and softness.

Best Side Dishes for Pineapple Upside-Down Sugar Cookies

Pairing side dishes with your Pineapple Upside-Down Sugar Cookies can enhance your dessert experience. Here are some great options:

1. Fresh Fruit Salad: A mix of seasonal fruits adds freshness and balances sweetness.
2. Yogurt Parfait: Layer yogurt with granola and fresh fruit for a delightful contrast.
3. Cheese Platter: A selection of mild cheeses pairs well with the cookie’s sweetness; try brie or goat cheese.
4. Chocolate Fondue: Dip cookie pieces into rich chocolate for an indulgent treat.
5. Nut Mix: A bowl of lightly salted nuts provides a crunchy, savory option alongside sweet cookies.
6. Herbal Tea: A warm cup of herbal tea can soothe after enjoying the sweetness of these cookies.

Common Mistakes to Avoid

When making Pineapple Upside-Down Sugar Cookies, it’s easy to overlook some details. Here are common mistakes to avoid for the best results.

• Skipping the Cooling Time: Don’t rush! Allowing the cookies to cool in the muffin tin helps them set properly and makes them easier to remove.
• Overmixing the Cookie Dough: Be gentle! Overmixing can lead to tough cookies; mix just until combined for a soft texture.
• Not Measuring Ingredients Accurately: Use proper tools! Accurate measurements ensure consistency in your cookies, so don’t eyeball it.
• Using Too Much Topping: Keep it balanced! Excess topping can spill over while baking, creating a mess. Stick to the recommended amounts.
• Ignoring Oven Temperature Preheating: Always preheat! Skipping this step can affect cookie texture and bake time. Make sure your oven is ready before you start baking.

Storage & Reheating Instructions

Refrigerator Storage

• Store in an airtight container for up to 5 days.
• Place parchment paper between layers to prevent sticking.

Freezing Pineapple Upside-Down Sugar Cookies

• Freeze in a single layer on a baking sheet before transferring to an airtight container.
• They can be frozen for up to 3 months.

Reheating Pineapple Upside-Down Sugar Cookies

• Oven: Preheat to 350°F (175°C) and warm cookies for about 5-7 minutes.
• Microwave: Heat individually on medium power for 10-15 seconds; monitor closely.
• Stovetop: Place in a skillet over low heat, covering with a lid for about 2-3 minutes until warmed through.

Frequently Asked Questions

If you have questions about making Pineapple Upside-Down Sugar Cookies, here are some answers!

How do I make Pineapple Upside-Down Sugar Cookies chewy?

To achieve a chewy texture, ensure you don’t overbake them. Remove the cookies from the oven when they are lightly golden at the edges.

Can I use fresh pineapple instead of canned?

Yes, fresh pineapple can be used! Just make sure it’s properly sliced and drained before using it as a topping.

How should I store leftover Pineapple Upside-Down Sugar Cookies?

Store any leftovers in an airtight container at room temperature for up to 5 days or freeze them for longer storage.

What can I substitute for maraschino cherries?

You can use fresh cherries or even chunks of strawberries as an alternative topping if desired!

Final Thoughts

These Pineapple Upside-Down Sugar Cookies blend soft, buttery cookie goodness with sweet caramelized fruit. They’re perfect for gatherings or as a delightful snack anytime. Feel free to customize the toppings with your favorite fruits or adjust sweetness levels. Enjoy experimenting with this versatile recipe!