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Pineapple Upside Sugar Cookies

DeShawn Mitchell
These delightful cookies combine the buttery goodness of sugar cookies with sweet, caramelized pineapple and a pop of color from maraschino cherries. Perfect for any occasion!
Prep Time 45 minutes
Cook Time 20 minutes
Total Time 1 hour 5 minutes
Course Dessert
Cuisine American
Servings 12 cookies
Calories 250 kcal

Ingredients
  

Cookie Base

  • 1/2 cup unsalted butter softened
  • 3/4 cup granulated sugar
  • 1 egg
  • 1 tsp vanilla extract
  • 1 1/2 cups all-purpose flour
  • 1/2 tsp baking powder
  • 1/4 tsp salt

Toppings

  • 1/4 cup unsalted butter melted
  • 1/2 cup brown sugar packed
  • 12 slices canned pineapple drained well
  • 6 maraschino cherries halved

Instructions
 

Preparing the Cookie Dough

  • Cream together softened butter and granulated sugar until fluffy, about 2-3 minutes, scraping down the sides of the bowl as needed.
  • Add egg and vanilla extract, mixing until well combined.
  • In a separate bowl, whisk together flour, baking powder, and salt. Gradually add dry ingredients to wet ingredients, mixing until just combined.
  • Wrap dough in plastic wrap and chill in the refrigerator for at least 30 minutes.

Arranging the Toppings

  • Preheat oven to 350°F (175°C).
  • In a small bowl, mix melted butter and brown sugar. Spoon mixture into each well of a muffin tin.
  • Place a pineapple ring and a halved maraschino cherry in the center of each well.
  • Roll chilled dough into 1-2 tablespoon balls, flatten slightly, and place on top of pineapple and cherry in each muffin tin well.

Baking

  • Bake for 18-20 minutes, or until edges are golden brown.
  • Cool in the muffin tin for a few minutes, then invert onto a wire rack to cool completely.

Notes

  • 1- Use cold ingredients for flakier biscuits.
  • 2- Taste the apple filling and adjust spices as needed.
  • 3- Serve warm with ice cream or whipped cream for an extra treat.
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