Oh my goodness, have you ever tried Pineapple Upside Down Sugar Cookies? They’re like a tropical vacation in cookie form! I remember the first time I made these delightful treats; I was trying to impress some friends with my baking skills, and instead of the usual sugar cookies, I decided to have a little fun and twist things up. The combination of soft, buttery cookies with sweet, caramelized pineapple and cherries on top is just out of this world! You get that classic sugar cookie flavor but with a fruity surprise that leaves everyone guessing. Trust me, the joy of pulling these cookies out of the oven and seeing that gorgeous golden brown color is unbeatable. Plus, the smell? Wow! It fills your kitchen with pure happiness. I can’t wait for you to try them!

Ingredients List

1 cup unsalted butter, softened
1 cup granulated sugar
2 large eggs
1 teaspoon vanilla extract
3 cups all-purpose flour
1 teaspoon baking powder
1/2 teaspoon salt
1 cup crushed pineapple, drained
1/2 cup brown sugar
1/4 cup maraschino cherries

How to Prepare Pineapple Upside Down Sugar Cookies

Step-by-Step Instructions

First things first, preheat your oven to 350°F (175°C). This step is key because you want your cookies to bake evenly and come out perfectly golden!
In a large mixing bowl, cream together the softened unsalted butter and granulated sugar until it’s light and fluffy. This usually takes about 2-3 minutes, and trust me, you’ll love the texture!
Next, crack in those 2 large eggs and add the teaspoon of vanilla extract. Mix it all together until it’s well blended. The smell will be divine!
In another bowl, whisk together the all-purpose flour, baking powder, and salt. This helps ensure that your cookies have that perfect lift. It’s like giving them a little pep talk!
Gradually add the dry ingredients to your buttery mixture. I like to do this in thirds—mixing until just combined after each addition. We don’t want to overwork the dough!
Now, it’s time to fold in that delicious crushed pineapple. Make sure it’s well-drained to avoid soggy cookies. Use a spatula to gently incorporate it into the dough.
In a separate small pan, melt the brown sugar over low heat. Once it’s melted and bubbly, pour it into the bottom of your cookie molds. This is where the magic happens!
Place a maraschino cherry right on top of the melted brown sugar in each mold. This adds a lovely touch of sweetness and color.
Scoop your cookie dough into the molds, making sure it covers the sugar and cherries completely. I usually use a cookie scoop for even portions, but you can use a tablespoon too!
Pop them in the oven and bake for about 12-15 minutes, or until they’re golden brown around the edges. Keep an eye on them though; every oven is a bit different, so adjust as needed!
Once baked, let them cool in the molds for a few minutes. Then, carefully invert them onto a plate. The anticipation is real! You’ll want to let them cool a bit more before devouring these little gems.

Why You’ll Love This Recipe

It’s a fun twist on classic sugar cookies with a tropical flair that brings joy to any gathering.
Quick and easy preparation means you can whip these up in no time—perfect for last-minute baking!
The combination of caramelized pineapple and maraschino cherries creates a unique flavor that’s both sweet and tangy.
They’re visually stunning, making them an impressive dessert to share at parties or potlucks.
These cookies are soft and chewy, with a delightful crunch from the caramelized sugar on the bottom.
Perfect for all ages—kids and adults alike will be delighted by this sweet surprise!
They can easily be made ahead of time and stored, so you can enjoy them fresh whenever you like!

Nutritional Information Section

When it comes to enjoying these delightful Pineapple Upside Down Sugar Cookies, it’s good to have an idea of what’s in them! Here’s a general breakdown of the nutritional information per cookie:

Calories: 150
Sugar: 10g
Sodium: 90mg
Fat: 7g
Saturated Fat: 4g
Unsaturated Fat: 2g
Trans Fat: 0g
Carbohydrates: 20g
Fiber: 0g
Protein: 1g
Cholesterol: 30mg

Keep in mind, though, that these values can vary based on the specific brands and ingredients you use. So, if you’re counting calories or adjusting for dietary needs, it’s always a good idea to double-check the labels on your products. Enjoy these cookies with a little mindfulness, and savor every bite!

Tips for Success

Now, let’s make sure your Pineapple Upside Down Sugar Cookies turn out absolutely perfect! Here are some of my best tips to ensure success:

Drain the Pineapple Well: This is super important! If your crushed pineapple isn’t drained enough, it can make the cookie dough too wet, leading to a soggy cookie. Give it a good squeeze with a paper towel if needed!
Watch the Oven: Every oven is a little different, so keep an eye on your cookies as they bake. They should be golden brown around the edges but still soft in the center when you take them out. If they look too pale, they might need a minute or two more!
Use Room Temperature Ingredients: Make sure your butter and eggs are at room temperature before you start. This helps them cream together nicely, creating that fluffy texture we all love!
Don’t Overmix: When you add the dry ingredients to the wet, mix just until combined. Overmixing can lead to tough cookies, and we want them to be soft and chewy!
Cool Before Inverting: Let the cookies cool for a few minutes in the molds before inverting them. This helps them set up and keeps the lovely caramel layer intact!
Experiment with Molds: If you don’t have cookie molds, don’t worry! You can use a muffin tin instead. Just make sure to adjust the baking time a bit, as they may need a little longer to bake.
Store Properly: Keep your leftover cookies in an airtight container to maintain their freshness. They’re best enjoyed within a few days, but trust me, they won’t last long!

Follow these tips, and you’ll be well on your way to creating the most delightful Pineapple Upside Down Sugar Cookies that everyone will rave about!

Variations

If you’re feeling adventurous or just want to mix things up a bit, there are so many fun variations you can try with these Pineapple Upside Down Sugar Cookies! Here are some ideas to spark your creativity:

Mango Madness: Swap out the crushed pineapple for crushed mango! It’ll give your cookies a sweet and tropical twist that’s just as delightful.
Berry Blast: Instead of pineapple, use a mix of crushed strawberries or blueberries. They’ll add a burst of color and a sweet-tart flavor that’s irresistible!
Coconut Cream: Add shredded coconut to your cookie dough for a tropical flair. You can even sprinkle some on top before baking for extra texture and flavor!
Gluten-Free Option: Substitute the all-purpose flour with a gluten-free flour blend. Just make sure it contains xanthan gum for the right texture!
Dairy-Free Delight: Use vegan butter and a flax egg (1 tablespoon ground flaxseed mixed with 2.5 tablespoons water) instead of regular butter and eggs for a dairy-free version!
Spiced Version: Add a teaspoon of cinnamon or nutmeg to the dough for a warm, spiced flavor that pairs beautifully with the fruit.
Chocolate Drizzle: After the cookies have cooled, drizzle some melted chocolate over the top for a decadent finish. Yum!
Nutty Crunch: Fold in some chopped nuts like walnuts or pecans for a satisfying crunch and added flavor!

Feel free to get creative and adjust the toppings or fillings based on your preferences! The base recipe is so versatile that you can easily tailor it to suit your taste buds or dietary needs. Have fun experimenting!

Serving Suggestions

Now that you’ve baked up a batch of these delightful Pineapple Upside Down Sugar Cookies, you might be wondering what to pair them with to elevate your dessert experience even further. Here are some of my favorite serving suggestions that really complement these tropical treats:

Coconut Milk or Cream: A chilled glass of coconut milk or a drizzle of coconut cream on top adds a creamy, tropical touch that pairs beautifully with the fruity flavors of the cookies.
Iced Tea: A refreshing iced tea, especially with a hint of lemon or mint, balances the sweetness and adds a nice, crisp contrast.
Vanilla Ice Cream: Serve the cookies warm alongside a scoop of vanilla ice cream. The melting ice cream over the cookies is pure bliss!
Pineapple Juice: For a fun, fruity twist, enjoy these cookies with a glass of chilled pineapple juice. It’s like a mini tropical getaway in every bite!
Chocolate Dipping Sauce: Melt some chocolate to dip half of the cookie into. The combination of chocolate and pineapple will surprise and delight your taste buds!
Fruit Salad: A light, refreshing fruit salad with fresh berries, mango, and kiwi offers a contrasting texture and flavor that pairs nicely with the cookies.
Whipped Cream: Top the cookies with a dollop of whipped cream for an extra layer of indulgence. You can even sprinkle some toasted coconut on top for added crunch!

Whether you’re enjoying them at a gathering or as a sweet treat for yourself, these serving suggestions will surely enhance your Pineapple Upside Down Sugar Cookies experience. Enjoy every delicious moment!

Storage & Reheating Instructions

Once you’ve baked these fabulous Pineapple Upside Down Sugar Cookies, you’ll want to store them just right to keep that delightful flavor and texture intact! Here’s how to do it:

Storing: Allow the cookies to cool completely before you store them. This prevents moisture from building up and making them soggy. Place the cooled cookies in an airtight container, layering them with parchment paper between each layer to keep them from sticking together. They’ll stay fresh for about 3-5 days at room temperature—if they last that long!
Freezing: If you want to save some for later, you can freeze them! Just make sure they’re fully cooled, then wrap each cookie in plastic wrap or foil. Place them in a freezer-safe bag or container, and they’ll keep well for up to 2 months. When you’re ready to enjoy them again, just let them thaw at room temperature.
Reheating: To bring back that warm, fresh-baked goodness, you can pop them in the microwave for about 10-15 seconds. But if you prefer a little crispness, place them in a preheated oven at 350°F (175°C) for 5-7 minutes. This will help revive that lovely texture and make the caramel layer a bit gooey again!

These tips will ensure your Pineapple Upside Down Sugar Cookies stay delicious, whether you’re enjoying them right away or saving some for later. Happy baking!

Pineapple Upside Down Sugar Cookies: 7 Irresistible Treats

Author: [email protected]
Prep Time: 20 minutes
Cook Time: 15 minutes
Total Time: 35 minutes
Yield: 24 cookies 1x
Category: Dessert
Method: Baking
Cuisine: American
Diet: Vegetarian

Print Recipe

Description

A delightful twist on classic sugar cookies with pineapple and a caramel topping.

Instructions

Preheat your oven to 350°F (175°C).
Cream together the butter and granulated sugar in a bowl.
Add eggs and vanilla extract, mixing well.
In another bowl, whisk together flour, baking powder, and salt.
Gradually add the dry ingredients to the wet mixture.
Fold in crushed pineapple.
In a separate pan, melt brown sugar and pour into the bottom of cookie molds.
Place maraschino cherries on top of the melted sugar.
Scoop cookie dough into molds over the sugar and cherries.
Bake for 12-15 minutes until golden.
Let cool before inverting onto a plate.

Notes

Ensure the pineapple is well-drained to avoid soggy cookies.
Adjust baking time based on your oven.
Store cookies in an airtight container.

Nutrition

Serving Size: 1 cookie
Calories: 150
Sugar: 10g
Sodium: 90mg
Fat: 7g
Saturated Fat: 4g
Unsaturated Fat: 2g
Trans Fat: 0g
Carbohydrates: 20g
Fiber: 0g
Protein: 1g
Cholesterol: 30mg

Keywords: Pineapple Upside Down Sugar Cookies, sugar cookies, pineapple dessert

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