Deep-Dish Pineapple Upside Down Cookies
There is something special about desserts that carry both nostalgia and creativity, and pineapple upside-down treats have always had a place in my kitchen. I have made a classic pineapple upside-down cake for years, and it even found its way into my Easy BBQ cookbook. Later, that same inspiration led me to create a pineapple upside-down bread pudding that quickly became a family and Internet favorite. With flavors that bright and familiar, it only seemed natural to take the next step and turn the idea into a cookie.
These deep-dish pineapple upside-down cookies capture the same golden caramel glow you get when pineapple melts into brown sugar and butter. The aroma takes me right back to those early recipe tests, when the kitchen filled with warm pineapple syrup and the cake released perfectly from the pan with its glossy top shining. Now that same moment of magic appears in a smaller, more playful form.
The combination of soft cookie dough, caramelized fruit, and a bright cherry center gives these cookies the charm of the original with the ease of a handheld dessert. They bring together familiarity, comfort, and pure fun in every bite.
