Traditional Pineapple Upside-Down Sugar Cookies

A playful twist on the classic dessert, these soft sugar cookies are topped with a pineapple ring that caramelizes in the oven, giving each cookie the look and flavor of a miniature pineapple upside-down cake.

Pineapple Upside-Down Sugar Cookies

Ingredients
Unsalted butter, softened – 1 cup
Granulated sugar – 1 cup
Large egg – 1
Vanilla extract – 1 teaspoon
All-purpose flour – 2 cups
Baking soda – 1 teaspoon
Salt – 1/2 teaspoon
Canned pineapple rings, drained and patted dry – 10–12 rings
Additional granulated sugar – for sprinkling

Instructions

Step 1: Prepare the Oven and Baking Sheets
Preheat your oven to 350°F (180°C). Line baking sheets with parchment paper and set them aside.

Step 2: Cream the Butter and Sugar
In a large bowl, beat the softened butter and granulated sugar together until the mixture is light and fluffy, about 2 to 3 minutes using an electric mixer.

Step 3: Add the Wet Ingredients
Beat in the egg and vanilla extract, mixing until the batter is smooth and well combined.

Step 4: Combine the Dry Ingredients
In a separate bowl, whisk together the flour, baking soda, and salt. Slowly add the dry mixture to the wet ingredients, mixing just until a soft dough comes together.

Step 5: Form the Cookies and Add Pineapple
Scoop roughly 2 tablespoons of dough onto the prepared baking sheets, spacing them about 2 inches apart. Press a dried pineapple ring gently onto each dough mound, flattening slightly. Cut the rings if necessary so they fit neatly on the cookies.

Step 6: Sprinkle and Bake
Lightly sprinkle granulated sugar over the pineapple rings. Bake for 11 to 13 minutes, or until the cookie edges turn lightly golden and the centers are set.

Step 7: Cool and Enjoy
Allow the cookies to cool on the baking sheets for a few minutes before transferring them to a wire rack to cool completely. Serve and enjoy.