Pineapple Upside-Down Sugar Cookies

Pineapple Upside-Down Sugar Cookies are a delightful twist on the classic dessert. These cookies combine the buttery richness of sugar cookies with the tropical sweetness of pineapple and cherries, creating a bite-sized treat that’s as beautiful as it is delicious. Whether you’re planning a summer picnic, a festive holiday gathering, or just craving something sweet, these cookies are bound to impress!

Why You’ll Love Pineapple Upside-Down Sugar Cookies

1. Tropical Bliss in Every Bite: The tangy pineapple and sweet maraschino cherries pair perfectly with the buttery cookie base.

2. Stunning Presentation: These cookies bring a burst of color and charm to any dessert table, thanks to the caramelized topping and vibrant fruit.

3. Easy to Make: This recipe requires no fancy techniques, and you’ll have a batch of these beauties ready in just 30 minutes.

4. Crowd-Pleaser: From kids to adults, these cookies are a hit every time.

Ingredients for Pineapple Upside-Down Sugar Cookies

For the Cookies:

1 cup unsalted butter, softened
1 cup granulated sugar
1 large egg
1 teaspoon vanilla extract
2 ½ cups all-purpose flour
1 teaspoon baking powder
½ teaspoon baking soda
½ teaspoon salt

For the Topping:

1 can (8 oz) pineapple slices, drained (reserve juice)
¼ cup unsalted butter
½ cup brown sugar, packed
Maraschino cherries (one for each cookie)

Tools You’ll Need

Mixing bowls
Hand or stand mixer
Small saucepan
Measuring cups and spoons
Parchment paper
Baking sheets
Cookie scoop or spoon
Wire rack

How to Make Pineapple Upside-Down Sugar Cookies

Step 1: Preheat the Oven

Preheat your oven to 350°F (175°C). Line two baking sheets with parchment paper to prevent sticking and ensure easy cleanup.

Step 2: Make the Cookie Dough

In a large mixing bowl, cream together the softened butter and granulated sugar until light and fluffy, about 3-4 minutes.
Add the egg and vanilla extract, mixing until fully combined.
In a separate bowl, whisk together the flour, baking powder, baking soda, and salt.
Gradually add the dry ingredients to the wet mixture, stirring gently until just combined.

Step 3: Prepare the Topping

In a small saucepan, melt the ¼ cup unsalted butter with the brown sugar over medium heat, stirring until bubbly and smooth.
Spoon about a tablespoon of the butter-sugar mixture onto each cookie spot on the prepared baking sheets.

Step 4: Assemble the Cookies

Place a pineapple slice on top of the butter-sugar mixture.
Add a maraschino cherry in the center of each pineapple slice.
Scoop about 1 tablespoon of cookie dough and gently spread it over each pineapple slice, leaving some of the fruit visible for a beautiful presentation.

Step 5: Bake to Perfection

Bake the cookies for 12-15 minutes, or until the edges turn light golden brown.
Let the cookies cool on the baking sheet for 5 minutes before transferring them to a wire rack to cool completely.

Tips for the Best Pineapple Upside-Down Sugar Cookies

Don’t Overmix: Overworking the dough can lead to tough cookies. Stir just until combined.
Drain Pineapples Well: To prevent soggy cookies, ensure the pineapple slices are thoroughly drained.
Custom Sizes: Use a pineapple tidbit or chunk if you prefer smaller cookies.

What to Serve with Pineapple Upside-Down Sugar Cookies

Pair these cookies with a scoop of vanilla ice cream or a dollop of whipped cream for an extra indulgent treat. For a refreshing drink, try serving them with iced tea or pineapple-infused water.

Storage Instructions

Room Temperature: Store cookies in an airtight container for up to 3 days.
Refrigeration: Keep them in the fridge for up to a week for a firmer texture.
Freezing: Freeze the cookies for up to 3 months. Thaw at room temperature before serving.

Frequently Asked Questions (FAQ)

Can I use fresh pineapple instead of canned?

Absolutely! Just slice the pineapple into thin rounds and ensure they’re well-drained before using.

Can I make these cookies gluten-free?

Yes, substitute the all-purpose flour with a 1:1 gluten-free baking flour.

What if I don’t have maraschino cherries?

You can use fresh cherries, raspberries, or even candied ginger for a unique twist.

Final Thoughts

These Pineapple Upside-Down Sugar Cookies are a tropical dream come true. With their caramelized topping and soft, buttery cookie base, they’re a dessert that’s as delightful to eat as they are to make. Perfect for any occasion, they’ll transport your taste buds to a sunny paradise with every bite.