Pineapple Upside Down Sugar Cookies (Printable)
Soft sugar cookies with caramelized pineapple and maraschino cherry topping, inspired by classic upside-down cake flavors.
# What You'll Need:
→ For the 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
→ For the 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 Steps:
01 - Preheat oven to 350°F. Line two baking sheets with parchment paper.
02 - Melt 4 tablespoons butter in small saucepan over medium heat. Add brown sugar, stirring until dissolved and bubbling, about 2 minutes. Remove from heat.
03 - Spoon 1 teaspoon caramel mixture onto each baking spot, spacing 2 inches apart. Top each with pineapple pieces and half a cherry.
04 - Whisk together flour, baking soda, cream of tartar, and salt in medium bowl.
05 - Beat softened butter with granulated sugar in large bowl until light and fluffy, about 2 minutes. Beat in egg and vanilla.
06 - Gradually add dry ingredients to wet mixture, mixing just until combined. Using 2-tablespoon cookie scoop, portion dough and roll into balls.
07 - Flatten dough balls slightly and place each atop prepared pineapple-cherry spots, pressing gently.
08 - Bake for 13-15 minutes until edges are just golden. Cool on pan for 5 minutes.
09 - Carefully invert each cookie onto wire rack so pineapple topping faces up. Cool completely before serving.
# Expert Suggestions:
01 -
- The caramelized pineapple creates a gooey, buttery topping that stays tender even after baking
- These cookies transport beautifully, making them ideal for picnics, bake sales, or sending care packages
02 -
- Invert cookies while still warm or the caramel will harden and stick to the parchment paper
- Space caramel spots generously since these cookies spread more than typical sugar cookies
03 -
- Use fresh pineapple if desired but pat it thoroughly dry to prevent soggy cookies
- For extra caramel flavor, sprinkle a pinch of sea salt over the warm cookies after inverting