Pineapple Upside Down Sugar Cookies (Print View)
Soft sugar cookies with caramelized pineapple and cherry topping, inspired by the classic upside-down cake.
# Ingredient List:
→ 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 mixed.
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, 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. Do not 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.
10 - Let cool on the sheet for 3 minutes, then carefully invert each cookie onto a wire rack while still warm to reveal the caramelized fruit topping. Cool completely before serving.
# Expert Advice:
01 -
- They look like tiny upside-down cakes but eat like soft, buttery cookies
- The caramelized fruit topping creates this gooey, sweet surprise in every bite
02 -
- Invert the cookies while they're still warm or the caramel will harden and stick to the parchment
- Well-drained pineapple is crucial. Too much liquid makes the cookies soggy underneath
03 -
- Chill the dough for 15 minutes if it feels too sticky to work with
- Space the caramel mounds carefully so the cookies don't bake into each other