Pineapple Upside Down Sugar Cookies (Printable)

Soft sugar cookies with caramelized pineapple and cherries for a tropical twist 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 Cook:

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). Arrange a few pineapple pieces and half a cherry over each butter-sugar mound, pressing gently to adhere.
04 - In a medium bowl, whisk together flour, baking powder, and salt until well blended.
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 the dry ingredients to the wet mixture, mixing just until a soft dough forms. Be careful not to overmix.
07 - Scoop 2-tablespoon portions of dough and flatten into thick discs. Place each disc over the pineapple-cherry topping, completely covering the fruit arrangement.
08 - Bake for 13-15 minutes, until edges are lightly golden and centers are set.
09 - 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. Cool completely before serving.

# Expert Tips:

01 -
  • The moment you flip these warm cookies and see that glistening caramelized fruit, you will feel like a pastry wizard
  • Soft sugar cookie base meets sticky sweet pineapple topping in every bite
  • They are faster than cake but deliver all the nostalgic flavors you remember
02 -
  • Flip the cookies while they are still warm or the caramel will harden and stick to the parchment
  • Space the caramel mounds carefully because the cookies will spread during baking
  • Drain your pineapple thoroughly or the extra moisture will make the cookies soggy underneath
03 -
  • Use a cookie scoop for uniform portions which helps them bake evenly
  • Work quickly when arranging fruit because the butter sugar mixture starts to set
  • If the cookies stick invert the entire parchment onto a rack and peel it off slowly

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