Pineapple Upside Sugar Cookies are a delightful twist on the classic pineapple upside-down cake. Instead of making one large cake, this recipe transforms the tropical, caramelized flavors into individual cookie-sized treats. They’re soft, buttery, slightly chewy, and topped with caramelized pineapple and cherries that look as beautiful as they taste. Perfect for parties, bake sales, or just a fun weekend baking project, these cookies give you all the nostalgia of the cake but in a grab-and-go size. If you love cookies with a bit of flair and tropical sweetness, these are bound to become a favorite.

Full Recipe

Ingredients

1 cup unsalted butter, softened
1 cup granulated sugar
1/2 cup brown sugar, packed
2 large eggs
2 teaspoons vanilla extract
2 1/2 cups all-purpose flour
1 teaspoon baking soda
1/2 teaspoon baking powder
1/2 teaspoon salt
1/2 cup crushed pineapple, drained well
1/4 cup pineapple juice (from the can)
1/2 cup maraschino cherries, halved
1/4 cup brown sugar (for topping)
2 tablespoons unsalted butter, melted (for topping)

Cooking Directions

Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper.
In a large mixing bowl, cream together the softened butter, granulated sugar, and 1/2 cup brown sugar until light and fluffy.
Beat in the eggs one at a time, then add vanilla extract. Mix until well combined.
In another bowl, whisk together flour, baking soda, baking powder, and salt. Gradually mix the dry ingredients into the wet mixture.
Fold in the drained crushed pineapple and pineapple juice until evenly combined.
In a small bowl, mix 1/4 cup brown sugar with 2 tablespoons melted butter. Place about 1 teaspoon of this mixture on the baking sheet where each cookie will go.
Add half of a maraschino cherry in the center of each sugar-butter circle, then place about 1 tablespoon of cookie dough over the top.
Gently flatten the cookie dough with the back of a spoon. Repeat with remaining dough.
Bake for 12–14 minutes, or until golden brown around the edges.
Allow cookies to cool for 5 minutes before carefully flipping them upside down to reveal the caramelized pineapple-cherry topping.
Serve warm or at room temperature.

Nutrients (per cookie, approx. 24 cookies)

Calories: ~160
Protein: 2g
Carbohydrates: 23g
Fat: 7g
Saturated Fat: 4g
Fiber: <1g
Sugar: 15g
Sodium: 95mg

Why You’ll Love This Recipe

These cookies combine the fun of a sugar cookie with the charm of a pineapple upside-down cake. They’re soft and chewy with a gooey, caramelized top that makes them look bakery-worthy. Plus, they’re portioned into individual servings, which makes them easy to share. They’re festive enough for holidays but simple enough for a weekday treat, making them a recipe you’ll keep coming back to.

The Origins and Inspiration Behind the Dish

The classic pineapple upside-down cake became popular in the U.S. in the 1920s when canned pineapple became widely available. Its iconic caramelized pineapple rings and cherries made it a retro dessert staple. These cookies are inspired by that tradition but made modern by shrinking the concept into cookies. It’s a creative way to pay homage to a vintage dessert while making it more portable and fun for today’s gatherings.

Ingredient Spotlight

Pineapple is the star here—bringing tropical sweetness and moisture to the cookies. Using canned pineapple keeps the recipe simple and accessible year-round. The brown sugar topping is what creates that caramelized effect, melting into the pineapple and cherry as the cookies bake. The maraschino cherry not only adds a pop of color but also a sweet contrast to the tangy pineapple. All of this sits atop a buttery sugar cookie base that holds everything together.

Storage and Reheating Tips

These cookies can be stored in an airtight container at room temperature for up to 3 days. Because of the pineapple topping, they may get a little sticky, so layering them with parchment paper helps. For longer storage, refrigerate for up to a week. They can also be frozen for up to 2 months—just thaw at room temperature before serving. To enjoy them warm again, pop them in the microwave for about 10 seconds.

Common Variations to Try

You can have fun with these cookies by making little changes. Try swapping the cherries for candied ginger for a spicier tropical note. Add shredded coconut to the cookie dough for extra texture and flavor. You can also make mini muffin tin versions where the topping caramelizes perfectly and creates little “pineapple upside cupcakes.” If you like a stronger tropical vibe, replace some of the vanilla extract with coconut or rum extract.

Pairing Recommendations

These cookies pair beautifully with light beverages like iced tea, lemonade, or a tropical punch. For a cozy evening, try them with hot tea or coffee. If you’re serving them as part of a dessert spread, they go well with vanilla ice cream or a dollop of whipped cream. Their sweet and tangy flavor also makes them a wonderful companion to a sparkling wine or champagne for a celebratory touch.

Health Benefits

While these cookies are definitely a treat, they bring a few perks thanks to the pineapple. Pineapple is rich in vitamin C, manganese, and antioxidants that support the immune system and overall health. Even though sugar and butter make these indulgent, the fruit component adds natural sweetness and moisture. Enjoying them in moderation can satisfy your sweet tooth while giving you a little boost of tropical fruit goodness.

Conclusion

Pineapple Upside Sugar Cookies are a fun and creative dessert that blends classic inspiration with modern convenience. They’re eye-catching, delicious, and versatile enough for everything from casual snacks to party platters. If you love pineapple upside-down cake but want a quicker, more shareable version, this recipe is the perfect solution. Sweet, chewy, fruity, and slightly caramelized—these cookies prove that sometimes the best recipes are the ones that take a beloved favorite and give it a playful new twist.

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