Pineapple Upside Sugar Cookies take all the fun of pineapple upside-down cake and pack it into a soft sugar cookie base topped with a juicy pineapple ring and bright maraschino cherry. The buttery cookie dough, coconut, and caramelized fruit flavors make them feel like a tropical, handheld dessert that looks impressive but is easy to assemble.
Why you’ll love these cookies
This recipe follows the same basic structure as many pineapple upside-down sugar cookies: a simple sugar cookie dough, well-drained pineapple slices, and cherries arranged on top before baking. The cookies bake at 350°F until lightly golden, giving you tender, chewy centers with a lightly crisp edge and a soft, juicy fruit topping.
Shredded coconut mixed into the dough adds extra chew and “piña colada” vibes, similar to pina colada and coconut–pineapple cookie recipes. Draining the pineapple and cherries well keeps the tops pretty and prevents soggy spots, a tip emphasized in nearly all pineapple upside cookie methods.
Continue to the next page to get the full ingredients and steps