These pineapple upside-down sugar cookies bring a cheerful, tropical spin to a beloved classic. Soft, buttery, and gently sweet, each cookie is crowned with a caramelized pineapple ring that gives it the nostalgic charm of an upside-down cake—just in a handheld form. The combination feels both familiar and fun, making these cookies perfect for casual get-togethers, potlucks, or a simple weekend baking project.

To get started, cream softened unsalted butter with granulated sugar until the mixture becomes pale and fluffy. Beat in an egg and a splash of vanilla extract to create a smooth, cohesive base. In a separate bowl, whisk together the all-purpose flour, baking soda, and salt. Blend the dry ingredients into the butter mixture a little at a time until a soft dough forms. This straightforward cookie dough provides a tender texture that lets the pineapple flavor take center stage.

Portion the dough onto parchment-lined baking sheets, leaving space between each mound. Pat the pineapple rings dry—this step helps them caramelize rather than steam—then gently press a ring onto each scoop of dough. If the rings are too large, trim them slightly for a better fit. A light dusting of sugar over the fruit encourages a golden, lightly caramelized finish while baking.

Bake the cookies in a preheated 350°F (180°C) oven for 11 to 13 minutes, or until the edges are just turning golden and the centers look set. Allow them to cool on the baking sheet for a few minutes before transferring to a wire rack. Once cooled, they’re ready to enjoy: bright, sweet, and delicately tropical—like a bite-size vacation in cookie form.