Pineapple Upside Down Sugar Cookies: A Sweet and Fun Treat

Pineapple Upside Down Sugar Cookies are a delightful dessert that brings the beloved flavors of the classic pineapple upside-down cake into an easy-to-make cookie form. These soft, chewy cookies feature a sweet sugar cookie base topped with a juicy pineapple ring and a vibrant maraschino cherry, making them the perfect treat for summer gatherings, potlucks, or any festive occasion.

Whether you’re hosting a barbecue or simply craving a tropical-inspired cookie, these Pineapple Upside Down Sugar Cookies offer a fun and delicious twist on an old favorite. The combination of the soft sugar cookie with the caramelized pineapple topping will transport your taste buds to a tropical paradise.

Why You’ll Love Pineapple Upside Down Sugar Cookies

Pineapple Upside Down Sugar Cookies are not just a treat for the eyes but also a real crowd-pleaser. The recipe is incredibly easy to follow, making it ideal for both seasoned bakers and beginners. With simple ingredients like butter, sugar, and canned pineapple, you can make this cookie anytime, even if you’re short on time. Plus, it’s a great way to use canned pineapple, so you can enjoy this sweet treat year-round.

These cookies are a great choice for those who love fruity desserts but want something a bit more portable and fun than a traditional cake. They’re perfect for parties, holiday cookie exchanges, or just as a special snack for your family.

Ingredients You Need for Pineapple Upside Down Sugar Cookies

Here’s what you’ll need to make these delicious cookies:

For the Cookie Dough:

• Butter: Adds richness and a soft texture to the dough.
• Granulated Sugar: Sweetens the cookie base.
• Egg: Binds the ingredients and adds moisture.
• Vanilla Extract: Enhances the overall flavor.
• Powdered Sugar: Gives the cookie dough a fine, smooth texture.
• Vegetable Oil: Keeps the cookies moist and soft.
• Baking Soda: Helps the cookies rise.
• Cream of Tartar: Ensures the cookies remain soft and chewy.
• All Purpose Flour: The main structure of the cookie dough.

For the Pineapple Topping:

• Pineapple Rings: Adds the iconic tropical flavor and juiciness to the cookies.
• Maraschino Cherries: Provides a sweet, vibrant finish to each cookie.
• Brown Sugar: Sweetens and caramelizes the pineapple topping.
• Butter: Helps bind the topping and adds richness.

Alternative Ingredient Suggestions

If you’re looking to make substitutions, there are several options available:

• Pineapple: While canned pineapple is recommended for its sweetness and convenience, you can use fresh pineapple slices if preferred. Just be aware that the texture may vary slightly.
• Maraschino Cherries: You could swap these with fresh cherries or even another fruit like raspberries for a unique flavor twist.
• Butter: For a dairy-free version, use a plant-based butter alternative.

Step-by-Step Instructions to Make Pineapple Upside Down Sugar Cookies

Follow these simple steps to create your Pineapple Upside Down Sugar Cookies:

1. Preheat the Oven: Set your oven to 350°F (175°C) and allow it to heat up.
2. Prepare the Topping: In a small mixing bowl, combine ½ cup of melted butter and 1 cup of brown sugar. Stir until fully mixed.
3. Set the Pineapple Rings: Drain the canned pineapple rings and set them aside. Place a tablespoon of the butter and brown sugar mixture into each muffin tin well. Top each with one pineapple ring, then place a maraschino cherry in the center of each ring.
4. Make the Cookie Dough: Cream together softened butter and granulated sugar until light and fluffy. Add the egg and vanilla extract, continuing to beat for 2-3 minutes.
5. Add Dry Ingredients: Gradually add the vegetable oil, powdered sugar, and dry ingredients (flour, baking soda, and cream of tartar) to the wet mixture. Mix until fully combined.
6. Form the Cookie Dough: Scoop out cookie dough using a #24 cookie scoop. Flatten each dough ball to about 3 inches in diameter. Place each flattened dough on top of a pineapple ring, gently pressing the edges into the muffin tin to seal.
7. Bake: Bake in the preheated oven for 8-10 minutes, or until the edges are golden and the centers are no longer glossy.
8. Cool and Serve: Once baked, flip the muffin tin onto a parchment-lined cookie sheet. Allow the cookies to cool before serving to ensure they firm up.

Tips & Tricks for Perfect Pineapple Upside Down Sugar Cookies

• Avoid Overbaking: Keep an eye on your cookies to ensure they don’t overbake. The edges should be golden and the center should no longer appear glossy.
• Use a Muffin Tin: A muffin tin helps create the perfect cookie shape and holds the pineapple topping in place. If you don’t have one, a cookie sheet will also work, but the cookies may spread more.
• Chill the Dough: If you want a firmer cookie, chill the dough for about 15-20 minutes before baking. This will help the cookies keep their shape.

Pairing Ideas and Variations

These Pineapple Upside Down Sugar Cookies pair wonderfully with a scoop of vanilla ice cream or a dollop of whipped cream. For an extra touch, dust the cookies with powdered sugar just before serving.

You can also experiment with different fruit toppings for variety:

• Peach Topping: Try substituting pineapple with fresh or canned peach slices for a juicy, sweet twist.
• Coconut: Add shredded coconut to the cookie dough for a tropical flair.
• Gluten-Free Version: Replace the all-purpose flour with a gluten-free flour blend to make these cookies suitable for those with dietary restrictions.

Health Benefits of Pineapple Upside Down Sugar Cookies

While these cookies are primarily a treat, they do offer some health benefits, especially from the pineapple. Pineapple is rich in vitamin C, which helps support the immune system. Additionally, the bromelain enzyme found in pineapple can aid in digestion. Paired with the sweetness of a sugar cookie base, these cookies are a perfect balance of flavor and fun.

Storing and Freezing Pineapple Upside Down Sugar Cookies

Store your cookies in an airtight container at room temperature for up to 7 days. For the best taste, enjoy them within 2-3 days. If you want to store them for longer, freezing is an option. However, keep in mind that the pineapple and cherry topping may become a bit watery once thawed. For best results, freeze the cookies without the fruit topping, then add fresh fruit when you’re ready to serve.

Conclusion

Pineapple Upside Down Sugar Cookies are a fun, tropical twist on the classic dessert that everyone loves. With their soft, chewy sugar cookie base and delicious pineapple and cherry topping, these cookies are sure to become a new favorite in your baking repertoire. Whether you’re making them for a party, a holiday gathering, or just as a sweet treat to enjoy with your family, these cookies will bring smiles to everyone’s faces. They are easy to make, versatile, and sure to be a hit on any occasion.

So, grab your muffin tin and get baking! These cookies are perfect for experimenting with different toppings, flavors, and variations. Enjoy the refreshing taste of pineapple in a bite-sized cookie form that’s just as charming as it is delicious.

Frequently Asked Questions

More Relevant Recipes

• Pumpkin Snickerdoodle Cookies: These warm, spiced cookies combine the classic snickerdoodle flavor with a touch of pumpkin, making them a perfect fall treat. The soft texture and cinnamon-sugar coating make them a delightful option for pumpkin lovers looking for a twist on traditional snickerdoodles.
• Apple Cider Cookies: Infused with the flavors of apple cider, these cookies are a great choice for fall baking. They’re soft, chewy, and full of cozy, comforting flavors, making them a great pairing for Pineapple Upside Down Sugar Cookies during the autumn season.
• Pumpkin Pie Dip: For a no-bake, creamy dessert, try this pumpkin pie dip. It’s a fun and easy way to enjoy the flavors of pumpkin pie with a lighter twist, perfect for dipping cookies or enjoying with a spoon for a sweet treat that pairs wonderfully with Pineapple Upside Down Sugar Cookies.

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