1 cup unsalted butter, softened
1 cup granulated sugar
1 large egg
1 teaspoon vanilla extract
2 cups all-purpose flour
1 teaspoon baking powder
1/4 teaspoon salt
For the Topping:
1 fresh pineapple, peeled, cored, and sliced into thin rounds (or use pre-sliced canned pineapple rings, drained)
1/2 cup packed brown sugar
1/4 cup unsalted butter, melted
Optional: Maraschino cherries for garnish
Step-by-Step Instructions
1. Preheat and Prep
Preheat your oven to 350°F (175°C).
Line a baking sheet with parchment paper or silicone baking mats.
2. Prepare the Cookie Dough
In a large mixing bowl, cream together the softened butter and granulated sugar until light and fluffy.
Beat in the egg and vanilla extract until fully combined.
In a separate bowl, whisk together the flour, baking powder, and salt.
Gradually add the dry ingredients to the wet ingredients, mixing until a soft dough forms.
3. Assemble the Cookies
Place about 1 tablespoon of brown sugar in the center of each cookie spot on the prepared baking sheet.
Drizzle a small amount of melted butter over the brown sugar.
Place a pineapple ring on top of each brown sugar mound.
Scoop about 1–2 tablespoons of cookie dough and flatten it slightly with your hands. Place the dough on top of the pineapple ring, gently pressing it to cover the pineapple completely.
4. Bake to Perfection
Bake the cookies for 10–12 minutes, or until the edges are golden brown and the cookies are set.
Remove the cookies from the oven and let them cool on the baking sheet for 5 minutes.
5. Flip and Serve
Carefully flip each cookie upside-down onto a plate or cooling rack to reveal the caramelized pineapple topping.
If desired, place a maraschino cherry in the center of each pineapple ring for a pop of color.
Serve warm or at room temperature and enjoy the tropical goodness!
Tips for Success
Use Fresh Pineapple: Fresh pineapple adds a juicier, more vibrant flavor, but canned rings work well in a pinch—just pat them dry to remove excess moisture.
Don’t Skip the Brown Sugar: The brown sugar melts into a caramel-like layer that pairs beautifully with the pineapple.
Chill the Dough (Optional): If the dough feels too soft, chill it for 15–20 minutes before assembling the cookies for easier handling.
Experiment with Shapes: Use mini pineapple rings or cut larger rings into smaller pieces for bite-sized cookies.
Make Ahead: Assemble the cookies ahead of time and freeze them unbaked. Add a couple of extra minutes to the baking time if cooking from frozen.
Why This Recipe Works
These Pineapple Upside Sugar Cookies take the beloved flavors of Pineapple Upside-Down Cake and transform them into a portable, bite-sized treat. The buttery sugar cookie base provides a soft, melt-in-your-mouth texture, while the caramelized brown sugar and juicy pineapple create a sweet, sticky topping that’s impossible to resist. It’s a creative twist on a classic dessert that’s both nostalgic and refreshingly new.
Conclusion: A Tropical Treat Everyone Will Love
Whether you’re hosting a summer party, craving a tropical-inspired snack, or simply looking to try something different, these Pineapple Upside Sugar Cookies are sure to impress. Their unique presentation, vibrant flavors, and easy preparation make them a standout dessert that’s perfect for any occasion. Plus, their playful design is sure to bring smiles to everyone who tries them.
We’d love to see your creations! Tag us in your photos or share your favorite variations—your twist on these tropical cookies might just inspire others to try them too! 🍍🍪✨
