Pineapple Upside Down Sugar Cookies (Printable)

Soft sugar cookies with caramelized pineapple and cherry topping for a tropical spin on the classic upside-down favorite.

# 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), spacing them evenly 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 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 Tips:

01 -
  • The caramelized fruit topping creates a stunning presentation that looks like you spent hours in the kitchen
  • These cookies are perfectly portable unlike traditional upside-down cake
  • The soft chewy texture combined with sweet fruit is absolutely addictive
02 -
  • Drain pineapple really well or the cookies will be soggy underneath
  • Work quickly when flipping the cookies because the caramel sets fast
  • The fruit topping goes on the baking sheet first before adding the dough on top
03 -
  • Use a small ice cream scoop to portion the dough evenly
  • Chill the dough for 15 minutes if it gets too soft to work with

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