Pineapple Upside Down Sugar Cookies (Printable version)
Soft sugar cookies with caramelized pineapple and maraschino cherry topping. A nostalgic twist on a classic cake.
# List of ingredients:
→ 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 Cookie Dough
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, room temperature
12 - 2 teaspoons vanilla extract
# Directions:
01 - Preheat oven to 350°F. Line two baking sheets with parchment paper.
02 - Melt 4 tablespoons butter in a small saucepan over medium heat. Add brown sugar and stir constantly until dissolved and bubbling, about 2 minutes. Remove from heat.
03 - Spoon approximately 1 teaspoon caramel mixture onto each baking spot, spacing 2 inches apart. Top each with a few pineapple pieces and half a maraschino cherry.
04 - In a medium bowl, whisk together flour, baking soda, cream of tartar, and salt until well blended.
05 - In a large bowl, beat softened butter and granulated sugar with an electric mixer on medium-high speed until light and fluffy, approximately 2 minutes. Add egg and vanilla, beating until incorporated.
06 - Gradually add dry ingredients to the butter mixture, mixing on low speed just until combined. Do not overmix.
07 - Using a 2-tablespoon cookie scoop, portion dough and roll into balls. Flatten each ball slightly into a disc and place directly over prepared pineapple topping, pressing gently to adhere.
08 - Bake for 13-15 minutes until edges are lightly golden. Allow cookies to cool on the baking sheet for 5 minutes to set.
09 - Carefully flip each cookie onto a wire rack so the fruit topping faces upward. Cool completely before serving to allow the caramel to set.
# Expert Advice:
01 -
- These cookies deliver all the nostalgic comfort of pineapple upside-down cake in just two bites
- The caramelized fruit topping creates this incredible buttery sauce that seeps down into the soft cookie beneath
02 -
- Letting the cookies cool on the pan for those 5 minutes is non-negotiable—otherwise the caramel sticks to the parchment
- If you're using fresh pineapple, pat it really dry with paper towels or the extra moisture will make the cookies soggy
03 -
- If your caramel starts to seize up when you add the brown sugar, keep stirring—it'll smooth out again
- Position your cherries cut-side down for the prettiest presentation after flipping