If sunshine could be baked into a cookie, it would taste exactly like these Pineapple Upside Sugar Cookies. 🍍🍪 Bright, buttery, and bursting with tropical sweetness, these cookies take the charm of an old-fashioned pineapple upside-down cake and shrink it into bite-sized perfection.
Every cookie features a golden sugar-butter base that caramelizes just enough to give you that deliciously chewy edge, topped with crushed pineapple for a juicy pop of flavor and—if you’re feeling fancy—a maraschino cherry right in the center for that classic retro look. ✨
They’re a breeze to make, bake up in just 15 minutes, and are perfect for sharing (though you might not want to). Whether you’re dreaming of island breezes or just need a cheerful pick-me-up, these cookies will instantly transport you to your happy place. 🌞
Why You’ll Fall in Love with These Cookies
Sunshine in Every Bite
These cookies are pure joy in dessert form—soft, chewy sugar cookies meet the tropical tang of pineapple. The brown sugar caramelizes as they bake, creating that irresistible sticky-sweet layer that perfectly contrasts the buttery dough.
They’re like mini pineapple upside-down cakes but easier, faster, and totally portable. The pineapple adds natural sweetness and keeps the cookies moist for days, while the vanilla brings everything together with a comforting warmth.
Perfect for Parties, Gifts, or Everyday Indulgence
These cookies don’t just taste good—they look gorgeous, too! With their glistening pineapple tops and cherry centers, they’re the kind of dessert that catches everyone’s eye at bake sales, potlucks, and parties.
They also make perfect edible gifts—stack a few in a pretty box or jar, and you’ve got a homemade treat that feels personal and tropical all at once. Whether it’s a rainy afternoon bake or a summer picnic dessert, Pineapple Upside Sugar Cookies fit every occasion.
Ingredients You’ll Need
The Cookie Dough Base
- ½ cup unsalted butter, softened – Adds richness and structure to the cookies.
- ¾ cup granulated sugar – For sweetness and that classic sugar cookie flavor.
- 1 large egg – Binds everything together and keeps the cookies soft.
- 1 teaspoon vanilla extract – Adds aroma and depth.
- 1½ cups all-purpose flour – The perfect balance for chewy and tender cookies.
- ½ teaspoon baking powder – Gives a subtle lift.
- ¼ teaspoon salt – Balances sweetness and enhances flavor.
The Pineapple Topping and Garnish
- ½ cup crushed pineapple, well-drained – The star of the show! Adds fruity brightness and moisture.
- ¼ cup packed brown sugar – Creates that signature upside-down caramel layer.
- 1 tablespoon unsalted butter, melted – Helps the brown sugar caramelize perfectly.
- Maraschino cherries, halved (optional) – A pop of color and classic finishing touch.
Simple pantry staples come together to make something extraordinary—proof that great baking doesn’t need fancy ingredients.