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

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

Step 3: Prepare the Topping

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

Step 4: Assemble the Cookies

1. Place a pineapple slice on top of the butter-sugar mixture.
2. Add a maraschino cherry in the center of each pineapple slice.
3. 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

1. Bake the cookies for 12-15 minutes, or until the edges turn light golden brown.
2. 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.

Don’t Stop Here!

If you loved this recipe, check out these other fruity delights:

• Peach Cobbler Bars
• Coconut Pineapple Muffins
• Tropical Fruit Salad

Have you tried this recipe? Leave a review below, and don’t forget to share your creations on Pinterest. Let’s spread the cookie love!

Nutritional Information (Per Cookie)

• Calories: 150
• Fat: 7g
• Carbohydrates: 20g
• Protein: 2g
• Sugar: 10g