Name: Pineapple Upside-Down Sugar Cookies
Prep time: 15 min
Cook time: 12 min
Total time: 27 min
Cuisine: Tropical
Ingredients: 1/2 cup unsalted butter, softened; 1 cup granulated sugar; 1 large egg; 1 teaspoon vanilla extract; 1 1/2 cups all-purpose flour; 1/2 teaspoon baking soda; 1/4 teaspoon salt; 1/4 cup maraschino cherries, chopped; 1/2 cup crushed pineapple, drained; 1 tablespoon brown sugar; 2 tablespoons unsalted butter (for topping)

These Pineapple Upside-Down Sugar Cookies are a fun twist on the classic pineapple upside-down cake. A soft sugar cookie base, topped with a caramelized pineapple and a maraschino cherry, creates a tropical treat that’s perfect for any occasion. The unique combination of sweet and fruity flavors makes these cookies irresistible.

Why You’ll Love This Recipe

I love this recipe because it’s a creative spin on a beloved classic. It brings the tropical flavors of pineapple upside-down cake into bite-sized cookies, which makes them the perfect treat for any summer gathering or sweet craving. The pineapple caramel adds a rich, sweet flavor, and the maraschino cherry on top gives it that iconic touch. Plus, they’re incredibly easy to make and bake quickly, so you can enjoy them in no time. These cookies are sure to be a hit!

Ingredients

(Tip: You’ll find the full list of ingredients and measurements in the recipe card below.)

1/2 cup unsalted butter, softened

1 cup granulated sugar

1 large egg

1/2 teaspoon baking soda

1 teaspoon vanilla extract

1 1/2 cups all-purpose flour

1/4 teaspoon salt

1/4 cup maraschino cherries, chopped

1/2 cup crushed pineapple, drained

1 tablespoon brown sugar

2 tablespoons unsalted butter (for topping)

Directions

Preheat oven to 350°F (175°C) and line a baking sheet with parchment paper.

In a large bowl, cream together the softened butter and granulated sugar until light and fluffy. Add the egg and vanilla extract, beating until well combined.

In a separate bowl, whisk together the flour, baking soda, and salt. Gradually add the dry ingredients to the wet ingredients, mixing until just combined.

In a small saucepan over medium heat, melt the 2 tablespoons of butter for the topping. Add the brown sugar and cook, stirring frequently, until the mixture becomes a smooth caramel.

Remove the caramel from the heat and fold in the drained crushed pineapple. Let it cool slightly.

Scoop tablespoon-sized portions of the cookie dough onto the prepared baking sheet, spacing them about 2 inches apart.

Press a small indentation in the center of each dough ball. Spoon a small amount of the pineapple caramel mixture into the indentation, then top each cookie with a chopped maraschino cherry.

Bake the cookies for 10-12 minutes, or until the edges are golden brown. Remove from the oven and let them cool on the baking sheet for a few minutes before transferring to a wire rack to cool completely.

Servings and Timing

Prep time: 15 minutes

Cooking time: 12 minutes

Total time: 27 minutes

Servings: 12 cookies

Variations

Tropical Twist: Add a bit of shredded coconut to the pineapple caramel for an extra tropical flavor.

Chocolate Drizzle: After baking, drizzle some melted chocolate over the top for a chocolate-pineapple fusion.

Nutty Delight: Add chopped nuts, like macadamia nuts or walnuts, into the cookie dough or sprinkle on top for a bit of crunch.

Storage/Reheating

These cookies can be stored in an airtight container at room temperature for up to 3-4 days. For longer storage, keep them in the fridge for up to a week. If you’d like to enjoy them warm again, simply reheat them in the oven at 300°F (150°C) for about 5-7 minutes.

Related Recipes:

Pineapple Upside-Down Cheesecake

FAQs

How do I prevent the pineapple topping from making the cookies soggy?

I recommend draining the crushed pineapple well and even patting it dry with a paper towel before adding it to the caramel. This will help reduce the moisture and keep the cookies from becoming soggy.

Can I make these cookies ahead of time?

Yes! You can prepare the dough and store it in the fridge for up to 2 days before baking. You can also freeze the dough for up to 3 months. Just scoop the dough onto a baking sheet, freeze it, and then store it in a freezer-safe bag.

Can I substitute the maraschino cherries with another fruit?

Yes, you can use other fruits like diced mango or even a few slices of banana. However, keep in mind that maraschino cherries give it that signature pineapple upside-down cake flavor, so it’s worth trying at least once.

What can I use if I don’t have unsalted butter?

If you don’t have unsalted butter, you can use salted butter but reduce the amount of added salt in the recipe to balance out the flavors.

Can I make the caramel topping in advance?

The caramel topping is best made just before assembling the cookies so it stays warm and easy to spoon onto the dough. However, you can make it a few hours ahead, but be sure to let it cool and reheat it gently before using.

Conclusion

These Pineapple Upside-Down Sugar Cookies offer a delightful combination of sweetness and tropical flavors, making them the perfect treat for any time of year. They’re simple to make, fun to assemble, and perfect for sharing with friends and family. Whether for a summer party or just a snack with a tropical flair, these cookies are sure to become a new favorite!

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