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Pineapple Upside Down Sugar Cookies

Buttery sugar cookies topped with caramelized pineapple and cherries inspired by classic pineapple upside-down cake.
Print Recipe
Prep Time 15 minutes
Cook Time 15 minutes
Total Time 30 minutes
Servings: 12 cookies
Course: Dessert, Snack
Cuisine: American, Autumn
Calories: 230
Ingredients Equipment Method Notes

Ingredients
  

Pineapple Topping
  • 0.5 cup unsalted butter melted
  • 0.75 cup brown sugar
  • 12 pineapple rings drained
  • 12 maraschino cherries
Sugar Cookie Dough
  • 2 cups all-purpose flour
  • 1 tsp baking powder
  • 0.5 tsp salt
  • 0.5 cup unsalted butter softened
  • 0.75 cup granulated sugar
  • 1 egg large
  • 1 tsp vanilla extract
  • 2 tbsp pineapple juice

Equipment

  • Mixing bowls
  • Baking sheet
  • Wire rack
  • Hand mixer or stand mixer

Method
 

  1. Preheat oven to 350°F (175°C) and line baking sheet with parchment paper.
  2. Mix melted butter and brown sugar and place small spoonfuls on parchment for each cookie.
  3. Place pineapple pieces and cherries on top of the sugar mixture.
  4. Whisk flour, baking powder, and salt together.
  5. Cream butter and sugar, then mix in egg and vanilla.
  6. Add dry ingredients and pineapple juice to form dough.
  7. Place cookie dough over pineapple pieces.
  8. Bake 13–15 minutes until golden.
  9. Flip cookies while warm so pineapple topping faces up.

Notes

Pat pineapple dry before baking to prevent soggy cookies.