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Pineapple Upside Sugar Cookies

Pineapple Upside Sugar Cookies

Patricia Collins
These Pineapple Upside Sugar Cookies combine the nostalgic flavors of pineapple upside-down cake with a soft, chewy sugar cookie base. With crushed pineapple, coconut, and a brown sugar coating, they’re a tropical twist on a classic. A maraschino cherry in the center makes them as beautiful as they are delicious.
5 from 3 votes
Prep Time 15 minutes
Cook Time 15 minutes
Total Time 30 minutes
Servings 24 cookies
Calories 180 kcal

Ingredients
  

  • 1 cup unsalted butter softened
  • 1 cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract
  • cups all-purpose flour
  • ½ teaspoon baking powder
  • ¼ teaspoon salt
  • ½ cup crushed pineapple well-drained
  • ½ cup brown sugar for rolling
  • ¼ cup unsweetened shredded coconut
  • Maraschino cherries optional, for garnish

Instructions
 

  • Preheat oven to 350°F (175°C). Line baking sheets with parchment paper.
  • Cream butter and granulated sugar until light and fluffy.
  • Add egg and vanilla; beat until combined.
  • In a separate bowl, whisk flour, baking powder, and salt.
  • Gradually mix dry ingredients into wet ingredients until just combined.
  • Fold in crushed pineapple and shredded coconut.
  • Mix brown sugar with 1–2 teaspoon flour in a small bowl.
  • Scoop tablespoon-sized dough balls and roll in brown sugar mixture.
  • Place 2 inches apart on baking sheets and flatten slightly.
  • Optionally press a maraschino cherry into each center.
  • Bake 12–15 minutes until edges are golden.
  • Cool 5 minutes on the sheet, then transfer to a wire rack.

Notes

  • Drain pineapple well to prevent overly moist dough.
  • Add lime zest for extra tropical flavor.
  • Use parchment between cookie layers during storage.
  • Cookies freeze well; thaw at room temperature.
  • Optional glaze: mix powdered sugar with pineapple juice to drizzle.