Pineapple Upside Sugar Cookies

 

Pineapple Upside Sugar Cookies: A Tropical Twist on a Classic Favorite

If you love pineapple upside-down cake and sugar cookies, get ready—this recipe is about to blow your mind in the most delicious way possible. Introducing the sweet, chewy, tropical treat you didn’t know you needed: Pineapple Upside Sugar Cookies.

These cookies take all the nostalgic charm of a pineapple upside-down cake—juicy pineapple, caramelized brown sugar, and a cherry on top—and shrink it down into the perfect handheld dessert. Add in the buttery base of a soft sugar cookie, and you’ve got a flavor-packed bite that’s as cute as it is craveable.

I first tried these at a summer potluck where someone brought them on a whim, and they instantly became the talk of the table. “Wait... what are these?!” one person asked after the first bite. Within minutes, the plate was empty and everyone was asking for the recipe.

Here’s why Pineapple Upside Sugar Cookies are a must-bake:

• They’re easy to make with simple ingredients.

• They bring a fun, tropical twist to your cookie rotation.

• They look impressive, but require zero fancy decorating skills.

• They’re a hit at everything from bake sales and brunches to baby showers and backyard BBQs.

Each cookie is topped with a ring of pineapple and a maraschino cherry, then baked until the edges are golden and the sugar caramelizes into a gooey, buttery glaze. One bite and you’ll get soft cookie, tangy fruit, and that irresistible hint of brown sugar magic.

Whether you’re serving them warm with a scoop of vanilla ice cream or packing them up for a picnic, Pineapple Upside Sugar Cookies are sure to bring smiles and second helpings.

So go ahead—make a batch. And don’t be surprised if they disappear faster than the cake version ever did!