Craving the tropical flavors of pineapple and caramelized sugar in a handheld dessert? Look no further than these Pineapple Upside-Down Sugar Cookies! With a buttery sugar cookie base, caramelized pineapple, and a cherry on top, this recipe is perfect for summer parties, potlucks, or simply indulging your sweet tooth.

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Why You’ll Love This Recipe

These cookies are:

• Tropical and Sweet: The perfect balance of caramelized pineapple and buttery sugar cookie.
• Beautifully Unique: Each cookie is topped with a pineapple slice and cherry for an eye-catching dessert.
• Easy to Make: No cake pans required—just a baking sheet and a few simple ingredients.

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Ingredients

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)

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Directions

Preheat the Oven

1. Preheat your oven to 350°F (175°C). Line two baking sheets with parchment paper.

Make the Cookie Dough

2. Cream Butter and Sugar: In a large bowl, beat the softened butter and granulated sugar until light and fluffy, about 3–4 minutes.
3. Add Egg and Vanilla: Mix in the egg and vanilla extract until fully combined.
4. Mix Dry Ingredients: In a separate bowl, whisk together the flour, baking powder, baking soda, and salt.
5. Combine: Gradually add the dry ingredients to the wet mixture, stirring until just combined. Be careful not to overmix.

Prepare the Topping

6. Melt Butter and Sugar: In a small saucepan over medium heat, melt the ¼ cup of butter and brown sugar until bubbly and well combined.
7. Arrange Pineapple and Cherries: Spoon 1 tablespoon of the melted butter-sugar mixture onto the prepared baking sheet for each cookie. Top with a pineapple slice and place a maraschino cherry in the center of each slice.

Form the Cookies

8. Scoop Dough: Take about 1 tablespoon of cookie dough and gently press it over the pineapple slice. Flatten slightly to ensure it covers the fruit.

Bake

9. Bake: Place the cookies in the oven and bake for 12–15 minutes, or until the edges are lightly golden.
10. Cool: Allow the cookies to cool on the baking sheet for 5 minutes before transferring them to a wire rack to cool completely.

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Tips for the Best Pineapple Upside-Down Sugar Cookies

• Add Coconut: For an extra tropical twist, mix shredded coconut into the cookie dough.
• Chill the Dough: If your dough is too soft, refrigerate it for 15 minutes before forming the cookies.
• Storage: These cookies taste best fresh but can be stored in an airtight container for up to 3 days.

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Why These Cookies Will Be a Hit

Pineapple Upside-Down Sugar Cookies are the perfect combination of tropical flavors, buttery goodness, and a hint of nostalgia. They’re an ideal dessert for summer gatherings or anytime you want to impress your guests with a unique and delicious treat. The caramelized topping pairs beautifully with the soft sugar cookie, making every bite a delight!

Did you try this recipe? Share your photos and feedback in the comments below. Follow me for more creative and fun dessert ideas!