Pineapple Upside Sugar Cookies – A Tropical Twist on a Classic Treat
If you adore the nostalgic charm of classic pineapple upside-down cake but crave the convenience of a handheld dessert, these Pineapple Upside Sugar Cookies are about to become your new obsession. Each cookie features a buttery sugar cookie base crowned with a caramelized ring of pineapple and a sweet maraschino cherry — giving you all the juicy, buttery, tropical flavors of the original cake in a soft, chewy cookie form. They’re vibrant, fun, and irresistibly delicious, making them perfect for parties, holidays, bake sales, or anytime you want a dessert that truly stands out.
This recipe combines the best of both worlds: the melt-in-your-mouth crumb of a homemade sugar cookie and the rich, fruity topping of pineapple upside-down cake. With clear ingredients, detailed roles, and step-by-step instructions, this SEO-optimized recipe blog ensures you bake perfect cookies every time. Prepare for rave reviews — these cookies are beautiful, bold, and absolutely unforgettable.
Ingredients & What Each One Does
- 1 cup unsalted butter (softened) – Creates a rich, tender cookie base with perfect chew.
- 1 cup granulated sugar – Sweetens the cookie and helps achieve a lightly crisp edge.
- 1 large egg – Binds the dough and gives it soft structure.
- 2 teaspoons vanilla extract – Adds deep, warm flavor that enhances the pineapple topping.
- 2 1/2 cups all-purpose flour – Forms the structure of the cookie while keeping it soft and thick.
- 1 teaspoon baking powder – Helps the cookies rise slightly for a soft, fluffy bite.
- 1/4 teaspoon salt – Balances sweetness and enhances all flavors.
- 1/2 cup brown sugar – Creates the caramelized layer beneath the pineapple.
- 1/4 cup melted butter – Helps the brown sugar form a sticky, caramelized topping.
- 12 pineapple rings (drained & patted dry) – Provides the juicy tropical topping.
- 12 maraschino cherries – Completes the traditional pineapple upside design.
How to Make Pineapple Upside Sugar Cookies
- Prep the Pans: Line a muffin pan with parchment rounds or spray generously with nonstick spray. This helps the cookies release cleanly after baking.
- Create the Caramel Layer: In a small bowl, stir together the brown sugar and melted butter. Spoon a heaping teaspoon of the mixture into the bottom of each muffin cup.
- Add Pineapple & Cherry: Place a pineapple ring over the caramel mixture. Add a maraschino cherry to the center of each ring.
- Make the Sugar Cookie Dough: Cream the softened butter and granulated sugar until light and fluffy. Add the egg and vanilla extract, mixing until smooth.
- Combine the Dry Ingredients: Whisk together the flour, baking powder, and salt. Add slowly to the wet ingredients, mixing until a soft dough forms.
- Assemble: Scoop about 2 tablespoons of cookie dough and press it gently on top of each pineapple ring, covering the fruit completely.
- Bake: Bake at 350°F (175°C) for 16–20 minutes, or until the edges are lightly golden.
- Cool & Flip: Allow the cookies to cool for 5–7 minutes. Run a knife around the edges and gently flip each cookie onto a cooling rack to reveal the caramelized pineapple topping.
Why This Recipe Is Loved
- Perfect blend of flavors – buttery sugar cookies meet caramelized pineapple.
- Beautiful presentation – they look like mini pineapple upside-down cakes.
- Individually portioned – no slicing or messy cake pans.
- A crowd pleaser – ideal for potlucks, birthdays, and tropical-themed gatherings.
Pro Tips for Perfect Pineapple Upside Sugar Cookies
- Dry the pineapple well — prevents excess moisture in the cookie.
- Don’t skip the caramel layer — it creates the iconic sticky-sweet topping.
- Use a muffin pan — this keeps the pineapple perfectly shaped.
- Cool before flipping — ensures clean release and beautiful presentation.
- Add a pinch of cinnamon to the sugar cookie dough for extra warmth.
Serving Suggestions
These Pineapple Upside Sugar Cookies pair wonderfully with:
- A scoop of coconut or vanilla ice cream
- A drizzle of caramel sauce
- A tropical fruit salad
- A glass of iced tea, lemonade, or pineapple juice
Conclusion – Simple, Tropical, and Irresistibly Delicious
These Pineapple Upside Sugar Cookies capture everything you love about pineapple upside-down cake — the caramelized fruit, the buttery sweetness, and the nostalgic charm — all in a soft, chewy cookie. They’re easy to make, stunning to serve, and absolutely unforgettable. Whether you’re baking for a celebration or treating yourself to a tropical twist on a classic dessert, this recipe delivers outstanding flavor with minimal effort. With its clarity, depth, and exceptional quality content, this recipe is designed to outrank competing websites and become your go-to guide for this unforgettable treat.