Think of the warm, caramelized magic of a pineapple upside-down cake — that golden fruit topping glistening with sweet brown sugar glaze — now shrink that indulgence into a soft, buttery sugar cookie you can hold in one hand. That’s Pineapple Upside Sugar Cookies — the dessert that’s equal parts nostalgic, tropical, and utterly addictive.
These cookies combine the tender sweetness of sugar cookies with the bright, tangy juiciness of pineapple, all topped with a buttery brown sugar glaze that seeps into every bite. They’re not just cookies… they’re tiny edible vacations.
Why Pineapple Upside Sugar Cookies Are Irresistible
Classic sugar cookies are delicious on their own, but when you infuse them with caramelized pineapple goodness, they transform into something extraordinary. Each cookie delivers:
- A soft and chewy base — buttery, rich, and perfectly sweet.
- A juicy pineapple crown — sweet-tart and refreshing.
- A golden brown sugar glaze — the sticky, caramel-like finish that ties it all together.
It’s the perfect blend of comfort food and tropical sunshine.
What You’ll Need
For the topping:
- ¼ cup unsalted butter, melted
- ½ cup light brown sugar, packed
- Pineapple rings (canned or fresh), cut into smaller pieces to fit the cookies
- Maraschino cherries (optional, for the classic upside-down touch)
For the cookies:
- 1 cup unsalted butter, softened
- 1 cup granulated sugar
- 1 large egg
- 1 tsp vanilla extract
- 2 ½ cups all-purpose flour
- ½ tsp baking powder
- ¼ tsp salt