Pineapple Upside Down Sugar Cookies (Print Version)

Soft sugar cookies with caramelized pineapple and cherry topping for a tropical treat.

# 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

# 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 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 distributed.
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 combined.
07 - Gradually add the 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, 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. Cool completely before serving.

# Expert Tips:

01 -
  • You get all the nostalgic flavors of upside-down cake in under an hour with zero cake leveling anxiety
  • The moment you flip that warm cookie and see the glistening pineapple is pure kitchen magic
02 -
  • If you wait too long to flip these cookies, the fruit will stick to the parchment and you will have to scrape it off with sad results
  • The dough must be completely covering the fruit or you will have little pineapple islands floating on top instead of being nestled underneath
03 -
  • Pat your pineapple completely dry with paper towels before arranging it, otherwise your cookies will have soggy bottoms that nobody wants
  • Use a thin metal spatula to flip the cookies quickly and confidently, hesitation is your enemy here

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