Pineapple Upside Down Sugar Cookies (Printable)

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

# 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, packed

→ 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

# How to Make It:

01 - Preheat the oven to 350°F. Line two baking sheets with parchment paper.
02 - In a small saucepan, melt 4 tablespoons butter over medium heat. Add brown sugar and stir until dissolved and bubbling, about 2 minutes. Remove from heat.
03 - Spoon about 1 teaspoon of the 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 - In a medium bowl, whisk together flour, baking soda, cream of tartar, and salt.
05 - In a large bowl, beat softened butter with granulated sugar until light and fluffy, about 2 minutes. Beat in the egg and vanilla.
06 - Gradually add the 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 to 15 minutes, or until edges are just golden.
09 - Cool on the pan for 5 minutes, then carefully invert each cookie onto a wire rack so the pineapple topping is on top. Allow to cool completely before serving.

# Expert Suggestions:

01 -
  • The caramelized pineapple and cherry topping creates that nostalgic upside-down cake flavor in handheld form
  • Soft, buttery sugar cookie base perfectly balances the sweet fruit topping
  • Surprisingly simple despite their impressive appearance
02 -
  • The caramel hardens quickly, so work fast when spooning it onto the baking sheet
  • Inverting the cookies while still warm is crucial, otherwise the fruit sticks to the parchment
  • Room temperature ingredients prevent the caramel from seizing and ensure proper texture
03 -
  • If using fresh pineapple, cut it into smaller pieces than canned rings and pat thoroughly dry
  • The cookies are done when the edges are barely golden, they continue cooking on the hot pan

Return