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Pineapple Upside Down Sugar Cookies
A Classic Dessert Reimagined in Cookie Form
Pineapple Upside Down Sugar Cookies take everything we love about the nostalgic pineapple upside-down cake—the caramelized fruit, buttery sweetness, and eye-catching presentation—and transform it into a soft, handheld treat. These cookies are tender, golden, and topped with a glossy pineapple slice and cherry, making them perfect for parties, holidays, or anytime you want a dessert that looks as good as it tastes.
Unlike traditional cookies, these are baked “upside down” so the pineapple and caramel topping become the star once flipped. The result is a bakery-style cookie with a tropical twist and irresistible flavor.
Ingredients You’ll Need
For the Topping:
- Pineapple slices (canned rings, well-drained)
- Maraschino cherries, halved
- Unsalted butter
- Brown sugar
For the Sugar Cookie Dough:
- Unsalted butter, softened
- Granulated sugar
- Egg
- Vanilla extract
- All-purpose flour
- Baking powder
- Salt
Step-by-Step Method
Step 1: Prepare the Baking Pan
Preheat your oven to 350°F (175°C). Lightly grease a muffin tin or line it with parchment circles to prevent sticking. Using a muffin tin helps hold the pineapple slices in place and gives each cookie a neat shape.
Step 2: Create the Caramel Base
In a small bowl, mix melted butter with brown sugar until smooth. Spoon a small amount of this mixture into the bottom of each muffin cup, spreading it evenly. This layer will melt during baking, creating a rich caramel topping.
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