These Pineapple Upside-Down Sugar Cookies reimagine the beloved tropical cake as a soft, chewy cookie you can enjoy by hand. A rich sugar cookie dough provides a buttery base, while tangy pineapple rings add a caramelized, fruity topping. Thoroughly drying the pineapple and dusting it with sugar allows it to glaze perfectly in the oven without adding excess moisture to the dough.

How to Make Pineapple Upside-Down Sugar Cookies

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

Step 2: Add Wet Ingredients
Mix in the egg and vanilla extract, beating until the mixture is smooth and fully blended.

Step 3: Mix Dry Ingredients
In a separate bowl, whisk together the flour, baking soda, and salt. Slowly incorporate the dry ingredients into the wet mixture, mixing just until a soft dough comes together. Do not overmix.

Step 4: Portion and Top
Scoop roughly 2 tablespoons of dough per cookie and place them on the prepared baking sheets, leaving about 2 inches between each. Press a dried pineapple ring gently into the top of each dough portion, flattening slightly.

Tip: If the pineapple rings are too large, cut them in half or trim as needed.

Step 5: Add Sugar Topping
Lightly sprinkle additional granulated sugar over the pineapple. This enhances caramelization and adds a glossy finish.

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