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