Pineapple Upside-Down Sugar Cookies

If you’re looking for a delightful treat that brings a smile to anyone’s face, then these Pineapple Upside-Down Sugar Cookies are just the answer! Imagine soft, chewy cookies topped with luscious caramelized pineapple and a pop of cherry goodness. This recipe has been a favorite in my home for years, perfect for everything from busy weeknights to special family gatherings. The combination of flavors is simply irresistible, and the warm aroma that fills your kitchen while they bake is an experience all on its own!

These cookies not only taste amazing but also look stunning when served. They are sure to impress your friends and family, making them a fantastic addition to any dessert table. Let’s dive in and create some sweet memories together!

Why You’ll Love This Recipe

• Easy to make: With simple steps and common ingredients, you’ll have these cookies ready in no time!
• Family-friendly: Everyone loves the sweet pineapple and cherry topping—kids and adults alike will ask for seconds.
• Versatile serving options: Enjoy them warm straight out of the oven or let them cool for later snacking.
• Make-ahead convenience: These cookies store well, making them great for prepping ahead of time for parties or events.

Ingredients You’ll Need

Gathering the right ingredients is half the fun! You’ll find that these are simple, wholesome items you probably already have in your pantry. Let’s take a look at what we need to bring these Pineapple Upside-Down Sugar Cookies to life.

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

Variations

This recipe is wonderfully flexible! Feel free to get creative based on your preferences or what you have on hand. Here are some fun ideas to switch things up:

• Use different fruits: Try swapping out pineapple for peaches or mangoes for a tropical twist.
• Mix in nuts: Add chopped walnuts or pecans into the cookie dough for an extra crunch.
• Add spices: A sprinkle of cinnamon or nutmeg can add warmth and depth to your cookies.
• Try different extracts: Experiment with almond extract instead of vanilla for a unique flavor profile.

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. This ensures that your cookies come out easily without sticking! In a small bowl, mix together the melted butter and brown sugar until combined. Spoon about 1 tablespoon of this mixture into each muffin cup. This creates that delicious caramel base that will soak into the cookie as it bakes.

Step 2: Add Pineapple and Cherries

Next, place a few small pieces of pineapple on top of the brown sugar mixture in each muffin cup. These juicy bits will become beautifully caramelized while baking. Then press half of a maraschino cherry right in the center of each one—this adds both color and flavor!

Step 3: Make the Sugar Cookie Dough

In a large bowl, cream together the softened butter and granulated sugar until light and fluffy. This step is crucial because it helps incorporate air into your dough, giving your cookies that perfect soft texture. Beat in the egg and vanilla extract until well combined.

Step 4: Combine Dry Ingredients

In another bowl, whisk together the flour, baking powder, and salt. Mixing these dry ingredients separately ensures they are evenly distributed throughout the dough.

Step 5: Mix Wet and Dry Ingredients

Gradually add the dry mixture into your wet ingredients while mixing until you form a soft dough. Don’t overmix—just combine until everything is nicely incorporated!

Step 6: Assemble the Cookies

Take about 1 1/2 tablespoons of cookie dough and press it over the topping in each muffin cup. Gently flatten it so it covers all those lovely toppings evenly. This helps create that signature upside-down cookie shape!

Step 7: Bake Your Cookies

Pop them in the oven for about 12-15 minutes or until the edges are lightly golden brown. The smell will be heavenly as they bake!

Step 8: Cool Before Serving

Once baked, let them cool in the muffin tin for about 5 minutes before carefully flipping it over onto a parchment-lined surface or cooling rack. This allows all that delicious caramelized goodness to settle nicely on top.

Step 9: Enjoy!

Serve these warm or at room temperature. The combination of soft sugar cookie with caramelized pineapple topping is pure bliss! Enjoy every bite with family and friends.

Now you have everything you need to whip up these delightful Pineapple Upside-Down Sugar Cookies! Happy baking!

Pro Tips for Making Pineapple Upside-Down Sugar Cookies

Making these delightful cookies is a breeze, and with a few handy tips, you can ensure they turn out perfectly every time!

• Use Fresh Pineapple: Fresh pineapple will give you a brighter flavor and a better texture than canned. If using canned, make sure to drain it well to prevent excess moisture in the cookies.

• Room Temperature Ingredients: Ensure your butter and egg are at room temperature before starting. This helps the sugar cookie dough blend smoothly, resulting in a softer cookie.

• Don’t Overmix the Dough: Once you combine the wet and dry ingredients, mix just until they come together. Overmixing can lead to tough cookies, so keep it gentle!

• Cool Before Serving: Allow the cookies to cool in the muffin tin for a few minutes before flipping them over. This step helps them hold their shape and prevents any topping from sticking.

• Experiment with Flavors: Feel free to add spices like cinnamon or nutmeg into the cookie dough for an extra layer of flavor. Just a pinch can elevate your cookies to new heights!

How to Serve Pineapple Upside-Down Sugar Cookies

These Pineapple Upside-Down Sugar Cookies are not only delicious but also visually appealing! Here are some fun ways to present them for any occasion.

Garnishes

• Whipped Coconut Cream: A dollop of whipped coconut cream adds a light and fluffy texture that complements the sweetness of the cookies beautifully.
• Toasted Coconut Flakes: Sprinkling some toasted coconut flakes on top provides a crunchy contrast and enhances the tropical vibe of the dessert.

Side Dishes

• Fresh Fruit Salad: A refreshing mix of seasonal fruits balances the sweetness of the cookies while adding vibrant colors to your plate.
• Vanilla Ice Cream: Serving these warm cookies with a scoop of vanilla ice cream creates a delightful contrast between warm and cold, making each bite irresistible.
• Coconut Milk Beverage: A chilled glass of coconut milk adds a creamy texture that pairs wonderfully with the flavors in the cookies, making it a perfect drink option.
• Herbal Tea: A soothing cup of herbal tea, such as chamomile or mint, complements the sweet notes of your cookies without overpowering their flavor.

Enjoy serving these delightful treats at your next gathering or as an everyday indulgence!

Make Ahead and Storage

These Pineapple Upside-Down Sugar Cookies are perfect for meal prep, allowing you to enjoy delicious treats throughout the week without the hassle of making them from scratch each time. Whether you’re planning for a gathering or just want some sweet snacks on hand, follow these storage tips!

Storing Leftovers

• Store cooled cookies in an airtight container at room temperature for up to 3 days.
• For longer freshness, keep them in the fridge for up to a week.

Freezing

• Place fully cooled cookies in a single layer on a baking sheet and freeze until solid.
• Transfer cookies to a freezer-safe bag or container, separating layers with parchment paper, and freeze for up to 2 months.

Reheating

• To reheat frozen cookies, let them thaw at room temperature for about 30 minutes.
• Warm them in the oven at 350°F (175°C) for 5-7 minutes for that fresh-baked taste.

FAQs

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

Can I use fresh pineapple instead of canned?

Absolutely! Fresh pineapple can add a vibrant flavor. Just ensure it’s cut into small pieces similar to the canned variety.

How do I store Pineapple Upside-Down Sugar Cookies?

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

What if I don’t have maraschino cherries?

You can substitute with any other cherry variety or even omit them entirely. The cookies will still be delicious with just the caramelized pineapple topping!

How do I ensure my sugar cookies are soft?

Make sure not to overbake them! The edges should just be golden while the centers remain soft as they cool.

Final Thoughts

I’m so excited for you to try these Pineapple Upside-Down Sugar Cookies! With their delightful combination of flavors and textures, they’re sure to become a favorite treat in your home. Whether you’re sharing them with friends or enjoying them solo, I hope each bite brings you joy. Happy baking!