Pineapple Upside Down Sugar Cookies (Print version)

Soft sugar cookies with caramelized pineapple and maraschino cherries. A nostalgic twist on the classic upside-down cake.

# What you 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

# Directions:

01 - Preheat the oven to 350°F. Line two baking sheets with parchment paper.
02 - In a small saucepan, melt 4 tablespoons of 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 13-15 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 to cool completely before serving.

# Expert advice:

01 -
  • The caramelized pineapple and cherry topping creates that nostalgic cake flavor in just two bites
  • Soft, buttery sugar cookie base that stays tender for days
  • Easier than a full cake but delivers all the same nostalgia
02 -
  • Cooling the cookies for exactly 5 minutes before inverting is crucial, or the caramel will slide right off
  • Work quickly once you start spooning the caramel onto the baking sheets, as it thickens fast
  • Don't skip the parchment paper, or the caramel will weld itself to your baking sheets forever
03 -
  • Use a cookie scoop for uniform size and even baking
  • Rotate the baking sheets halfway through baking for consistent browning

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