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Irresistible Pineapple Upside Down Sugar Cookies

Prep Time 20 minutes
Chillling Time 12 minutes
Total Time 32 minutes
Servings 24 cookies

Ingredients
  

  • For the Cookie Dough
  • 1 cup unsalted butter softened
  • 1 cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 2 ½ cups all-purpose flour
  • 1 teaspoon baking powder
  • ½ teaspoon baking soda
  • ¼ teaspoon salt
  • For the Pineapple Topping
  • ½ cup finely diced fresh pineapple or canned, well-drained
  • 2 tablespoons brown sugar
  • 1 tablespoon unsalted butter melted
  • Optional: maraschino cherry halves for garnish

Instructions
 

  • Prepare the Pineapple Topping
  • Toss diced pineapple with brown sugar and melted butter. Set aside.
  • Make the Cookie Dough
  • Cream together butter and granulated sugar until light and fluffy.
  • Mix in the egg and vanilla extract until smooth.
  • Whisk together flour, baking powder, baking soda, and salt. Gradually add to wet ingredients until just combined.
  • Shape the Cookies
  • Preheat oven to 350°F (175°C) and line a baking sheet with parchment paper.
  • Scoop tablespoons of dough and gently flatten each into a disc.
  • Top each cookie with a spoonful of pineapple mixture and press gently. Add a cherry half if desired.
  • Bake
  • Bake 12–15 minutes until edges are lightly golden. Cool on the baking sheet for 5 minutes before transferring to a wire rack.

Notes

• Serve warm with vanilla ice cream for a mini dessert.
• Pair with pineapple juice or tropical cocktails.
• Perfect for summer picnics, brunches, or cookie trays.
• Garnish with extra cherries or toasted coconut for flair.