Pineapple Upside Down Sugar Cookies (Printable)
Soft sugar cookies with caramelized pineapple and maraschino cherry topping.
# 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
# How-To Steps:
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 spot (18 total). Arrange pineapple pieces and half a cherry over each mound, pressing gently to adhere.
04 - In a medium bowl, whisk together flour, baking powder, and salt until evenly combined.
05 - 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 incorporated.
06 - Gradually add dry ingredients to the wet mixture, mixing just until a soft dough forms. Do not overmix.
07 - Scoop 2-tablespoon portions of dough and flatten into thick discs. Place each disc directly over the fruit topping, completely covering the pineapple and cherry arrangement.
08 - Bake for 13-15 minutes until edges are lightly golden and centers are set.
09 - Let cookies cool on the baking sheet for 3 minutes. Carefully invert each cookie onto a wire rack while still warm to reveal the caramelized fruit topping. Cool completely before serving.
# Expert Advice:
01 -
- The caramelized fruit creates this gooey, buttery topping that feels like a little surprise in every bite
- These cookies travel beautifully to potlucks and somehow taste even better the next day
02 -
- Wait the full 3 minutes before flipping or the fruit will slide right off the warm cookie
- Really drain that pineapple, even pat it dry with paper towels, or your cookies will turn out soggy
03 -
- Use a cookie scoop for uniform portions so they all bake at the same rate
- If your dough feels too sticky, chill it for 15 minutes before scooping