Pineapple Upside Down Sugar Cookies

A Tropical Twist on a Classic Favorite

If you love the nostalgic flavors of pineapple upside-down cake and the soft, buttery comfort of sugar cookies, these Pineapple Upside Down Sugar Cookies are the perfect dessert fusion. Each cookie delivers a golden caramelized pineapple topping, a pop of cherry sweetness, and a tender sugar cookie base that melts in your mouth. They’re eye-catching, easy to make, and guaranteed to impress at parties, potlucks, or family gatherings.

🌟 Why You’ll Love These Cookies

All the flavors of pineapple upside-down cake in cookie form
Soft, buttery centers with a caramelized fruit topping
Perfectly portioned and easy to serve
Great make-ahead dessert for events

🧾 Ingredients You’ll Need

For the Pineapple Topping:

Pineapple rings or chunks (drained well)
Maraschino cherries, halved
Brown sugar
Melted butter

For the Sugar Cookie Dough:

All-purpose flour
Baking powder
Salt
Unsalted butter, softened
Granulated sugar
Egg
Vanilla extract

🥣 Step-by-Step Method

Step 1: Prepare the Pan

Preheat your oven to 350°F (175°C). Lightly grease a standard muffin tin—this helps form perfectly shaped cookies and keeps the pineapple topping in place.

Step 2: Create the Pineapple Base

In a small bowl, mix the melted butter and brown sugar until smooth. Spoon a small amount of this mixture into the bottom of each muffin cup.
Place a piece of pineapple on top, then press a cherry half into the center. This layer will caramelize beautifully during baking.