Sugar Cookies with Pineapple Upside-Down Flavor

These Pineapple Upside-Down Sugar Cookies take inspiration from the classic tropical cake and turn it into a soft, chewy treat you can easily enjoy by hand. A rich, buttery sugar cookie dough forms the base, while tangy pineapple rings create a lightly caramelized, fruity topping. Properly drying the pineapple and coating it with sugar helps it glaze beautifully in the oven without adding too much moisture to the dough.

Pineapple Upside-Down Sugar Cookies

Ingredients
Ingredient Amount
Unsalted butter, softened 1 cup
Granulated sugar 1 cup (plus extra for topping)
Egg 1 large
Vanilla extract 1 teaspoon
All-purpose flour 2 cups
Baking soda 1 teaspoon
Salt ½ teaspoon
Canned pineapple rings, well drained 10–12 rings

How to Make Pineapple Upside-Down Sugar Cookies

Step 1: Prepare the Dough Base
Preheat the oven to 350°F and line baking sheets with parchment paper. In a large bowl, beat the softened butter and 1 cup of sugar using an electric mixer for 2–3 minutes, until light and fluffy.

Step 2: Add Wet Ingredients
Add the egg and vanilla extract, mixing until smooth and fully combined.

Step 3: Combine Dry Ingredients
In another bowl, whisk together the flour, baking soda, and salt. Gradually add the dry mixture to the wet ingredients, mixing just until a soft dough forms. Avoid overmixing.

Step 4: Shape and Add Topping
Scoop about 2 tablespoons of dough per cookie and place on the prepared baking sheets, spacing them about 2 inches apart. Gently press a dried pineapple ring onto each portion, flattening slightly.

Tip: If the rings are too large, slice them in half or trim to fit.

Step 5: Sprinkle Sugar
Lightly dust extra granulated sugar over the pineapple. This helps create a caramelized, glossy finish.

Step 6: Bake and Cool
Bake for 11–13 minutes, until the edges are lightly golden. Let the cookies rest on the baking sheet for a few minutes before transferring to a wire rack to cool completely.