Pineapple Upside Down Sugar Cookies (Printable)
Soft sugar cookies topped with caramelized pineapple and maraschino cherries for a tropical spin on a classic favorite.
# 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:
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 spot (18 total), spacing evenly 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 thoroughly combined.
06 - In a large bowl, beat softened butter and granulated sugar until light and fluffy. Add egg and vanilla; beat until fully incorporated.
07 - Gradually add 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 to 15 minutes, until edges are lightly golden.
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 - Allow cookies to cool completely on the wire rack before serving.
# Expert Tips:
01 -
- You get all the nostalgic flavors of pineapple upside down cake in just two bites
- The caramelized fruit topping creates a gooey, buttery layer that seeps into the soft cookie beneath
02 -
- Work quickly when inverting the cookies because the caramel sets fast as it cools
- Really drain that pineapple well, otherwise the extra moisture makes the cookie soggy underneath
03 -
- Add a pinch of cinnamon to the brown sugar mixture for warm spice notes
- Serve with vanilla ice cream while still warm for the ultimate dessert experience