Pineapple Upside Down Sugar Cookies (Printable version)
Soft sugar cookies with caramelized pineapple and cherry topping for a tropical treat.
# What you need:
→ Fruit Topping
01 - 1 cup pineapple, diced (fresh or canned, well drained)
02 - 9 maraschino cherries, halved
03 - 3 tablespoons unsalted butter, melted
04 - 1/3 cup light brown sugar
→ Sugar Cookie Dough
05 - 2 1/4 cups all-purpose flour
06 - 1/2 teaspoon baking powder
07 - 1/4 teaspoon salt
08 - 3/4 cup unsalted butter, softened
09 - 1 cup granulated sugar
10 - 1 large egg
11 - 1 teaspoon vanilla extract
# How to make it:
01 - Preheat oven to 350°F. Line two large baking sheets with parchment paper.
02 - In a small bowl, combine melted butter and brown sugar until well blended.
03 - Place a teaspoon of the butter-sugar mixture in the center of each parchment-lined cookie spot (18 spots total, spaced apart).
04 - Arrange a few pineapple pieces and half a cherry over each butter-sugar mound, pressing gently to adhere.
05 - In a medium bowl, whisk together flour, baking powder, and salt until evenly combined.
06 - In a large bowl, cream softened butter and granulated sugar until light and fluffy, about 2-3 minutes. Add egg and vanilla; beat until fully incorporated.
07 - Gradually add the dry ingredients to the wet mixture, mixing just until a soft dough forms. Be careful not to overmix.
08 - Scoop 2-tablespoon portions of dough and flatten into thick discs. Place each disc over the pineapple-cherry topping, completely covering the fruit.
09 - Bake for 13–15 minutes until edges are lightly golden and centers are set.
10 - Let cool on the baking sheet for 3 minutes, then carefully invert each cookie onto a wire rack while still warm to reveal the caramelized fruit topping.
11 - Cool completely before serving to allow the caramel topping to set.
# Expert tips:
01 -
- The caramelized fruit topping creates pockets of gooey sweetness in every bite
- These cookies combine the nostalgia of vintage cake with the convenience of handheld treats
- You get all the tropical flavor without needing to flip an entire cake
02 -
- Working quickly to invert cookies while they're still warm makes the flipping process much easier
- Well-drained pineapple prevents soggy cookie bottoms, so pat it dry with paper towels
03 -
- Space your cookie mounds generously since these spread more than typical cookies
- Add a pinch of sea salt on top of the fruit before covering with dough for salted caramel flavor