Pineapple Upside Down Sugar Cookies (Printable Version)

Soft sugar cookies with caramelized pineapple and cherries for a nostalgic, summery dessert.

# What You'll Need:

→ Topping

01 - 1 cup canned pineapple rings, drained and cut into small pieces
02 - 8 maraschino cherries, halved
03 - 4 tablespoons unsalted butter
04 - 1/3 cup light brown sugar

→ Sugar Cookies

05 - 2 1/4 cups all-purpose flour
06 - 1/2 teaspoon baking soda
07 - 1/2 teaspoon cream of tartar
08 - 1/4 teaspoon salt
09 - 3/4 cup unsalted butter, softened
10 - 1 cup granulated sugar
11 - 1 large egg
12 - 2 teaspoons vanilla extract

# Directions:

01 - Preheat the oven to 350°F. Line two baking sheets with parchment paper.
02 - Melt 4 tablespoons butter in a small saucepan over medium heat. Add brown sugar and stir until dissolved and bubbling, about 2 minutes. Remove from heat.
03 - Spoon about 1 teaspoon caramel mixture onto each spot where a cookie will bake, spacing 2 inches apart. Top each with a few pieces of pineapple and half a cherry.
04 - Whisk together flour, baking soda, cream of tartar, and salt in a medium bowl.
05 - Beat softened butter with granulated sugar in a large bowl until light and fluffy, about 2 minutes. Beat in egg and vanilla.
06 - Gradually add dry ingredients to the wet mixture, mixing just until combined.
07 - Using a 2-tablespoon cookie scoop, portion dough and roll into balls. Flatten slightly, then place each dough disc atop a prepared pineapple-cherry spot, pressing gently.
08 - Bake for 13-15 minutes, or until edges are just golden. Cool on the pan for 5 minutes, then carefully invert each cookie onto a wire rack so the pineapple topping is on top.
09 - Allow cookies to cool completely before serving.

# Expert Advice:

01 -
  • You get all the gooey pineapple cherry goodness without spending an hour on a full cake
  • The caramelized topping creates a chewy gooey layer that keeps the cookie soft for days
02 -
  • Work quickly once the caramel is ready because it thickens fast and becomes hard to spoon
  • Invert cookies while still slightly warm or the caramel will glue them to the parchment paper forever
03 -
  • Use a cookie scoop for uniform sizing so all cookies bake at the same rate
  • Let the caramel cool for about 30 seconds before spooning so it does not spread too thin

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