Pineapple Upside Down Sugar Cookies (Printable)
Soft sugar cookies with caramelized pineapple and maraschino cherry topping, a twist on the classic upside-down cake flavor.
# 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
# Steps:
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 topping creates this incredible gooey layer that people can't quite identify but instantly love.
- These cookies strike the perfect balance between nostalgia and something new enough to feel exciting.
02 -
- Flipping the cookies while they're still warm is essential, or the caramel will harden and stick to the parchment paper.
- Don't skip the cream of tartar or you'll lose that distinctive sugar cookie flavor and texture.
03 -
- Room temperature ingredients are non-negotiable here—if your butter is too cold, the cookies won't spread properly.
- Don't overbake these cookies; they should still look slightly underdone in the center when you pull them out.