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Pineapple Upside Sugar Cookies

Emily Parker
Prep Time 15 minutes
Cook Time 15 minutes
Total Time 30 minutes
Servings 12 cookies
Calories 170 kcal

Ingredients
  

For the Pineapple Topping:

  • 1 cup crushed pineapple drained (reserve the juice)
  • 1/4 cup packed brown sugar
  • 1 tablespoon unsalted butter melted

For the Cookie Dough:

  • 1 cup unsalted butter softened
  • 1 cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 2 cups all-purpose flour
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon salt
  • 2 –3 tablespoons reserved pineapple juice

Substitution Tips:

  • Use canned pineapple tidbits finely chopped if crushed isn’t available.
  • Margarine can replace butter in a pinch but flavor may vary.

Instructions
 

Preheat and Prep

  • Preheat oven to 350°F (175°C). Grease a mini muffin tin or line a baking sheet with parchment paper. Tip: Use nonstick spray even in nonstick pans to ensure easy release.

Make the Pineapple Topping

  • In a small bowl, mix the drained pineapple, brown sugar, and melted butter. Tip: Drain pineapple thoroughly to avoid soggy cookies.

Make the Dough

  • In a large bowl, cream the softened butter and granulated sugar until light and fluffy. Beat in the egg and vanilla extract until smooth. In a separate bowl, whisk together flour, baking powder, and salt. Gradually add the dry ingredients to the butter mixture. Stir in 2–3 tablespoons of reserved pineapple juice to soften the dough. Tip: Chill the dough for 20 minutes if it feels too soft to scoop.

Assemble

  • For mini muffin tin version: Spoon about 1 teaspoon of the pineapple topping into each cup. Add a tablespoon of cookie dough on top and press gently.
  • For cookie sheet version: Drop dough by tablespoon, make a thumbprint in each, and fill the well with a bit of pineapple topping.

Bake

  • Bake for 12–14 minutes, or until edges are golden. Let cool in the pan for 5 minutes, then transfer to a wire rack. Tip: If using a muffin tin, run a knife around each cookie to release.

Notes

  • Drain Pineapple Well: Extra liquid will make cookies soggy.
  • Chill Dough If Needed: Helps hold shape during baking.
  • Creative Shapes: Use silicone molds for fun party-ready shapes.
  • Flavor Twist: Add a pinch of cinnamon or a dash of coconut extract for extra depth.