Sugar Cookies with Pineapple Upside-Down Flavor

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.


Pineapple Upside-Down Sugar Cookies

Ingredients

IngredientAmount
Unsalted butter, softened1 cup
Granulated sugar1 cup (plus more for topping)
Egg1 large
Vanilla extract1 teaspoon
All-purpose flour2 cups
Baking soda1 teaspoon
Salt½ teaspoon
Canned pineapple rings, drained well10–12 rings