Pineapple Upside-Down Sugar Cookies

Delight in the unique and delicious Pineapple Upside-Down Sugar Cookies! These cookies combine the soft, chewy texture of sugar cookies with a delightful topping of caramelized pineapple and cherries. Perfect for gatherings, parties, or just a sweet treat at home, they bring a tropical twist to your dessert table. The balance of flavors and textures makes them a standout choice for any occasion.

Why You’ll Love This Recipe

• Easy Preparation: Whip these cookies up in no time with simple steps that anyone can follow.
• Delicious Flavor: The combination of buttery sugar cookies with caramelized pineapple and cherries creates an irresistible treat.
• Versatile Dessert: Great for parties, potlucks, or just because; these cookies are sure to impress!
• Soft and Chewy Texture: Enjoy the perfect balance between a soft cookie base and a fruity topping that melts in your mouth.
• Fun Presentation: The upside-down style makes these cookies not only tasty but visually appealing too.

Tools and Preparation

Having the right tools can make your baking experience smoother and more enjoyable. Gather these essentials before starting to ensure everything goes seamlessly.

Essential Tools and Equipment

• Muffin tin
• Mixing bowls
• Electric mixer
• Measuring cups and spoons
• Parchment paper

Importance of Each Tool

• Muffin tin: This is crucial for shaping the cookies and giving them their distinctive upside-down look.
• Electric mixer: Saves time and effort when creaming butter and sugar together for a fluffy texture.
• Parchment paper: Prevents sticking and makes cleanup easier after baking.

Ingredients

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. Perfect for gatherings or a sweet treat anytime!

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 the softened butter and granulated sugar together until light and fluffy. Beat in the egg and vanilla extract until well combined. In another 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 and Serve

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. Serve warm or at room temperature. Enjoy the caramelized pineapple topping with the soft sugar cookie base!

How to Serve Pineapple Upside-Down Sugar Cookies

These delightful cookies are versatile and can be served in various ways to enhance their appeal. Here are some creative serving suggestions to elevate your Pineapple Upside-Down Sugar Cookies.

With Ice Cream

• Vanilla ice cream pairs beautifully with the warm cookies, creating a delicious contrast in temperature and flavor.
• For a tropical twist, try coconut or pineapple-flavored ice cream.

As Part of a Dessert Platter

• Arrange the cookies alongside fresh fruit, such as sliced strawberries or kiwi, for a colorful dessert spread.
• Add small bowls of chocolate sauce or caramel for dipping.

Drizzled with Glaze

• A simple glaze made from powdered sugar and milk can add sweetness and shine to the cookies.
• Consider infusing the glaze with coconut extract for an extra layer of flavor.

Garnished with Fresh Mint

• Adding fresh mint leaves on top of each cookie can enhance presentation and provide a refreshing taste.
• This is particularly appealing when serving at spring or summer gatherings.

How to Perfect Pineapple Upside-Down Sugar Cookies

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

• Use room temperature ingredients – Allow your butter and egg to sit at room temperature for optimal mixing and texture.
• Measure flour correctly – Spoon and level your flour for accurate measurements; too much flour can lead to dry cookies.
• Don’t overmix the dough – Once you combine wet and dry ingredients, mix just until incorporated to maintain a tender cookie.
• Monitor baking time – Keep an eye on the cookies as they bake; remove them when edges are lightly golden for best results.
• Cool properly – Let cookies cool in the muffin tin briefly before transferring them to a cooling rack to maintain their shape.

Best Side Dishes for Pineapple Upside-Down Sugar Cookies

Pairing side dishes with your Pineapple Upside-Down Sugar Cookies can create an enjoyable meal experience. Here are some great options to consider.

1. Fruit Salad – A mix of seasonal fruits like berries, melons, and citrus complements the sweet flavors of the cookies.
2. Yogurt Parfait – Layer yogurt with granola and fresh fruit for a healthy side that contrasts nicely with the cookies’ sweetness.
3. Cheese Platter – A selection of mild cheeses like brie or gouda can balance the sweet flavors while adding savory notes.
4. Chocolate Covered Strawberries – These treats add elegance and a touch of decadence that pairs well with dessert cookies.
5. Mini Quiches – Serve up some savory mini quiches for a delightful contrast against the sweet cookie flavors.
6. Nut Mix – Offer a bowl of roasted nuts for guests who enjoy a crunchy side; it adds texture alongside soft cookies.
7. Smoothies – Refreshing fruit smoothies can be an excellent beverage pairing, enhancing the tropical theme of these cookies.
8. Pineapple Salsa – A unique twist on traditional salsa made with fresh pineapple chunks offers a zesty complement that echoes cookie flavors.

Common Mistakes to Avoid

Baking can be tricky, and avoiding common pitfalls will help ensure your Pineapple Upside-Down Sugar Cookies turn out perfectly.

• Not measuring ingredients accurately: Use proper measuring cups and spoons. Accurate measurements are key for the right texture and taste.
• Overmixing the dough: Mix just until combined to avoid tough cookies. Overmixing can lead to dense sugar cookies that aren’t as soft and chewy.
• Skipping the cooling time: Allowing cookies to cool properly helps them set. Rushing this step can result in a messy presentation.
• Using cold butter: Make sure your butter is softened for easy creaming with sugar. Cold butter won’t blend well, affecting the cookie’s final texture.
• Not preheating the oven: Always preheat your oven before baking. This ensures even cooking and helps achieve a golden finish.

Storage & Reheating Instructions

Refrigerator Storage

• Store cookies in an airtight container for up to 1 week.
• Place parchment paper between layers to prevent sticking.

Freezing Pineapple Upside-Down Sugar Cookies

• Freeze cookies in a single layer on a baking sheet before transferring to a freezer-safe bag or container.
• They can be stored 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 minutes.
• Microwave: Heat one cookie for about 10-15 seconds for a warm treat.
• Stovetop: Place cookies in a skillet over low heat, cover, and warm for 2-3 minutes.

Frequently Asked Questions

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

Can I use fresh pineapple instead of canned?

Yes, fresh pineapple can be used! Just make sure to cut it into small pieces similar in size to the canned version.

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

Store them in an airtight container at room temperature or refrigerate them for longer freshness.

Can I customize the toppings on these cookies?

Absolutely! You can add other fruits like peaches or berries for different flavors while keeping the base cookie the same.

What makes these cookies soft and chewy?

The combination of softened butter and sugar creamed together creates air pockets that contribute to their softness when baked.

Final Thoughts

These Pineapple Upside-Down Sugar Cookies are not only delicious but also an exciting twist on a classic dessert. Their delightful blend of caramelized fruit atop a soft cookie base makes them perfect for any occasion. Don’t hesitate to customize with your favorite fruits or toppings!

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Pineapple Upside-Down Sugar Cookies

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• Author: Lara
• Total Time: 30 minutes
• Yield: Approximately 12 cookies 1x

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Description

Indulge in the delightful experience of Pineapple Upside-Down Sugar Cookies. These unique treats blend the soft, chewy goodness of sugar cookies with a mouthwatering topping of caramelized pineapple and cherries. Ideal for any occasion—from casual gatherings to festive celebrations—these cookies offer a tropical flair and a wonderful balance of flavors and textures.

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Ingredients

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• 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
• 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

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Instructions

1. Preheat your oven to 350°F (175°C) and prepare a muffin tin with parchment liners.
2. For the topping, mix melted butter and brown sugar in a small bowl. Spoon about 1 tablespoon into each muffin cup, add pineapple pieces, and press half a cherry on top.
3. In a large bowl, cream together softened butter and granulated sugar until fluffy. Beat in the egg and vanilla extract.
4. In another bowl, whisk together flour, baking powder, and salt. Gradually combine dry ingredients with wet ingredients until a soft dough forms.
5. Press about 1 ½ tablespoons of dough over each muffin cup's topping.
6. Bake for 12-15 minutes or until lightly golden around the edges.
7. Cool in the tin for 5 minutes before flipping onto a cooling rack.

• Prep Time: 15 minutes
• Cook Time: 15 minutes
• Category: Dessert
• Method: Baking
• Cuisine: Tropical

Nutrition

• Serving Size: 1 cookie (40g)
• Calories: 150
• Sugar: 10g
• Sodium: 100mg
• Fat: 6g
• Saturated Fat: 4g
• Unsaturated Fat: 2g
• Trans Fat: 0g
• Carbohydrates: 22g
• Fiber: 0g
• Protein: 1g
• Cholesterol: 20mg