Sugar Cookies with Pineapple Upside-Down Flavor

These Pineapple Upside-Down Sugar Cookies transform the classic tropical cake into a soft, chewy cookie that’s easy to enjoy by hand. A buttery sugar cookie base pairs perfectly with tangy pineapple rings that caramelize as they bake. Thoroughly drying the pineapple and lightly coating it with sugar helps create a glossy, golden topping without adding extra 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

Instructions

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

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

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

Step 4: Shape and Top
Scoop about 2 tablespoons of dough for each cookie and place on the prepared baking sheets, spacing them about 2 inches apart. Gently press a dried pineapple ring onto the top of each dough mound, slightly flattening it.

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

Step 5: Sprinkle with Sugar
Lightly dust the pineapple with additional granulated sugar to encourage caramelization and a shiny finish.

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