Pineapple Upside Down Sugar Cookies (Print Version)

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

# What You Need:

→ For the Topping

01 - 1 cup (200 g) canned pineapple rings, drained and cut into small pieces
02 - 8 maraschino cherries, halved
03 - 4 tablespoons (55 g) unsalted butter
04 - 1/3 cup (65 g) light brown sugar

→ For the Sugar Cookies

05 - 2 1/4 cups (280 g) 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 (170 g) unsalted butter, softened
10 - 1 cup (200 g) granulated sugar
11 - 1 large egg
12 - 2 teaspoons vanilla extract

# How to Prepare:

01 - Preheat the oven to 350°F (175°C). 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 irresistible gooey texture everyone fights over
  • They come together in under an hour but taste like you spent all day in the kitchen
  • Perfect for sharing at picnics, barbecues, or whenever you need a taste of summer nostalgia
02 -
  • Cooling the cookies on the pan for exactly 5 minutes before flipping is crucial, otherwise the fruit will slide right off
  • The caramel mixture hardens quickly, so work efficiently when spooning it onto the baking sheet
  • Room temperature ingredients are non-negotiable here, cold butter won't cream properly and you'll end up with tough cookies
03 -
  • If using fresh pineapple, pat it thoroughly with paper towels to prevent excess moisture from making the cookies soggy
  • Don't overbake, these cookies continue cooking on the hot pan and you want them to stay soft

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