Pineapple Upside Down Sugar Cookies (Printable Version)
Soft sugar cookies with caramelized pineapple and cherry topping. A bite-sized tropical delight ready in 40 minutes.
# What You'll 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
# Directions:
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 smooth.
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 blended.
06 - In a large bowl, beat softened butter and granulated sugar until light and fluffy, about 2-3 minutes. Add egg and vanilla; beat until fully combined.
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, fully covering the fruit.
09 - Bake for 13-15 minutes, until edges are lightly golden and centers are set.
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.
11 - Cool completely before serving to allow flavors to set.
# Expert Advice:
01 -
- These cookies deliver all the nostalgic flavors of retro upside-down cake in just two bites
- The caramelized fruit topping creates a gooey, sweet surprise in every cookie
02 -
- The 3-minute cooling window before flipping is critical—wait too long and the fruit bonds to the parchment, flip too soon and the topping slides off
- Draining your pineapple thoroughly is the difference between cookies and a soggy mess—press the diced pineapple between paper towels if using fresh
03 -
- Use a cookie scoop for uniform dough portions so all cookies bake at the same rate
- Adding 1/4 teaspoon almond extract to the dough creates a subtle bakery-style flavor that pairs beautifully with pineapple