Pineapple Upside-Down Sugar Cookies

Delight your taste buds with these Pineapple Upside-Down Sugar Cookies! This delicious treat combines a soft and chewy sugar cookie base topped with caramelized pineapple and cherries, making them perfect for any occasion. Whether it’s a family gathering or a cozy night in, these cookies are sure to impress with their unique flavor and delightful appearance.

Why You’ll Love This Recipe

  • Irresistible flavor: The combination of buttery sugar cookies with sweet caramelized pineapple and cherries creates a mouthwatering experience.
  • Easy to make: With simple steps and common ingredients, you’ll whip up these cookies in no time.
  • Versatile treat: Perfect for parties, potlucks, or just as a sweet snack at home.
  • Fun presentation: The upside-down style adds an eye-catching twist that everyone will love.
  • Soft and chewy texture: These cookies remain soft and chewy, ensuring a satisfying bite every time.

Tools and Preparation

Before you begin baking your Pineapple Upside-Down Sugar Cookies, gather the necessary tools. Having everything ready will streamline your cooking process and ensure success.

Essential Tools and Equipment

  • Muffin tin
  • Mixing bowls
  • Whisk
  • Spatula
  • Parchment paper

Importance of Each Tool

  • Muffin tin: This tool is essential for shaping the cookies into individual portions while holding the caramelized toppings.
  • Mixing bowls: Having multiple bowls helps keep wet and dry ingredients separate for better mixing results.
  • Whisk: A whisk makes it easy to combine dry ingredients evenly, ensuring a fluffy cookie dough.
  • Spatula: Use a spatula to smoothly incorporate ingredients together without overmixing.
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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: Prepare the Topping

Preheat your oven to 350°F (175°C) and lightly grease or line a muffin tin with parchment rounds. In a small bowl, mix the melted butter and brown sugar until well 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 2: 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 another bowl, whisk together the flour, baking powder, and salt. Gradually add the dry ingredients to the wet mixture, mixing until a soft dough forms.

Step 3: 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 4: Bake

Bake the cookies for 12-15 minutes, or until the edges are lightly golden. Let them cool in the muffin tin for about 5 minutes before carefully flipping it over onto a parchment-lined surface or cooling rack.

Step 5: Serve

Serve warm or at room temperature. Enjoy your delightful Pineapple Upside-Down Sugar Cookies!

How to Serve Pineapple Upside-Down Sugar Cookies

These delightful cookies can be enjoyed in various ways, making them a versatile treat for any occasion. Whether you’re hosting a party or simply indulging at home, here are some creative serving suggestions.

With a Scoop of Ice Cream

  • Serve warm cookies with a scoop of vanilla or coconut ice cream for a creamy contrast to the soft cookie and caramelized topping.

Drizzled with Chocolate Sauce

  • Enhance the flavors by drizzling melted chocolate over the cookies for an extra touch of sweetness.

Paired with Fresh Fruit

  • Fresh slices of mango or strawberries can complement the pineapple flavor and add a refreshing element to your dessert spread.

Accompanied by Whipped Cream

  • Top each cookie with fluffy whipped cream to create a light and airy finish that balances the richness of the sugar cookie.

As Part of a Dessert Platter

  • Arrange Pineapple Upside-Down Sugar Cookies on a dessert platter alongside other treats like brownies and fruit tarts for a decadent display.

How to Perfect Pineapple Upside-Down Sugar Cookies

Making these cookies perfect requires attention to detail. Here are some helpful tips for achieving the best results.

  • Use Room Temperature Ingredients: Ensure your butter and egg are at room temperature for better mixing and texture.

  • Don’t Overmix the Dough: Mix just until combined to keep the cookies soft and chewy. Overmixing can lead to tougher cookies.

  • Chill the Dough: If time permits, chill the dough for 30 minutes before baking. This helps maintain their shape during baking.

  • Watch Baking Time: Keep an eye on your cookies as they bake. Remove them when edges are lightly golden to avoid drying out.

  • Store Properly: Store leftovers in an airtight container at room temperature for up to three days to keep them fresh and chewy.

Best Side Dishes for Pineapple Upside-Down Sugar Cookies

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

  1. Coconut Sorbet: A refreshing and tropical addition that complements the pineapple’s sweetness without overpowering it.

  2. Tropical Fruit Salad: A colorful mix of fruits like kiwi, mango, and berries adds freshness and balance to the rich flavors of the cookies.

  3. Lemonade: A chilled glass of lemonade provides a zesty contrast that enhances the overall taste experience with its tartness.

  4. Vanilla Pudding: Smooth vanilla pudding creates a creamy pairing that contrasts nicely with the cookie’s textures.

  5. Caramel Dip: A small bowl of caramel sauce allows guests to dip their cookies, adding an extra layer of sweetness.

  6. Nutty Granola: Serve granola on the side for added crunch and texture, enhancing each bite with its nutty flavors.

Common Mistakes to Avoid

When making Pineapple Upside-Down Sugar Cookies, it’s easy to make mistakes that can affect the outcome. Here are some common pitfalls and how to avoid them.

  • Using cold butter: Start with softened butter for the sugar cookie dough to ensure a light and fluffy texture. Cold butter can lead to dense cookies.
  • Not measuring ingredients accurately: Use proper measuring cups and spoons for both dry and wet ingredients. This ensures the right balance of flavors and textures in your cookies.
  • Overmixing the dough: Mix just until combined after adding dry ingredients. Overmixing can result in tough cookies rather than soft and chewy ones.
  • Skipping the cooling time: Allow cookies to cool in the muffin tin for 5 minutes before flipping them out. Skipping this step can cause them to break apart.
  • Ignoring oven temperature: Always preheat your oven correctly. An oven that’s too hot or too cool can lead to uneven baking.
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Storage & Reheating Instructions

Refrigerator Storage

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

Freezing Pineapple Upside-Down Sugar Cookies

  • Freeze cookies for up to 3 months in a freezer-safe container.
  • Wrap individual cookies in plastic wrap before placing them in the container.

Reheating Pineapple Upside-Down Sugar Cookies

  • Oven: Preheat the oven to 350°F (175°C) and bake for about 5-7 minutes until warmed through.
  • Microwave: Heat each cookie for about 15-20 seconds on a microwave-safe plate. Be careful not to overheat, as they can become tough.
  • Stovetop: Warm cookies in a skillet over low heat for a couple of minutes, covering with a lid to help retain moisture.

Frequently Asked Questions

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

What is the best way to store 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 Pineapple Upside-Down Sugar Cookies?

Absolutely! You can use other fruits like peaches or strawberries instead of pineapple, or even mix nuts into the topping.

How do I know when my Pineapple Upside-Down Sugar Cookies are done?

Check for lightly golden edges; if they are golden but still soft in the center, they will firm up as they cool.

Can I use fresh pineapple instead of canned?

Yes, you can use fresh pineapple. Just ensure it’s ripe and cut into small pieces similar to canned pineapple.

Final Thoughts

Pineapple Upside-Down Sugar Cookies combine sweet caramelized fruit with a soft, buttery base, making them irresistible. These cookies are versatile; feel free to experiment with different fruits or toppings. Give this recipe a try for your next gathering or as a delightful treat any day!

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Pineapple Upside-Down Sugar Cookies

Pineapple Upside-Down Sugar Cookies


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

Description

Delight in the tropical flavors of Pineapple Upside-Down Sugar Cookies, a fun twist on a classic dessert! Soft and chewy sugar cookies serve as a perfect base for caramelized pineapple and cherries, creating a treat that’s both visually stunning and delicious. Whether you’re celebrating a special occasion or simply want to indulge in something sweet, these cookies will impress family and friends with their unique flavor profile and eye-catching upside-down presentation. Easy to make with accessible ingredients, this recipe is ideal for bakers of all skill levels. Serve them warm or at room temperature, and enjoy the delightful combination of buttery cookie goodness with the bright taste of caramelized fruit.


Ingredients

Scale
  • 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

Instructions

  1. Preheat oven to 350°F (175°C). Grease or line a muffin tin with parchment paper.
  2. In a bowl, combine melted butter and brown sugar; spoon 1 tablespoon into each muffin cup. Add pineapple pieces and press cherries on top.
  3. Cream softened butter and granulated sugar until fluffy; mix in egg and vanilla.
  4. In another bowl, whisk flour, baking powder, and salt; gradually add to the wet mixture until soft dough forms.
  5. Scoop 1 ½ tablespoons of dough over the topping in each cup; flatten gently.
  6. Bake for 12-15 minutes until edges are golden. Cool for 5 minutes before flipping onto a cooling rack.
  • Prep Time: 15 minutes
  • Cook Time: 15 minutes
  • Category: Dessert
  • Method: Baking
  • Cuisine: American

Nutrition

  • Serving Size: 1 cookie (40g)
  • Calories: 170
  • Sugar: 10g
  • Sodium: 90mg
  • Fat: 7g
  • Saturated Fat: 4g
  • Unsaturated Fat: 2g
  • Trans Fat: 0g
  • Carbohydrates: 25g
  • Fiber: 0g
  • Protein: 2g
  • Cholesterol: 20mg

Keywords: For a twist, try different fruits like peaches or strawberries as toppings. Chill the dough for 30 minutes before baking to maintain shape. Enjoy warm with ice cream or drizzled chocolate for an extra special treat.

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