Go Back

Pineapple Upside Down Sugar Cookies

Soft sugar cookies topped with caramelized pineapple and cherries.
Prep Time 25 minutes
Cook Time 15 minutes
Total Time 40 minutes
Servings: 18 cookies
Course: Dessert, Snack
Cuisine: American, Autumn
Calories: 210

Ingredients
  

Cookie Dough
  • 2 cups all-purpose flour
  • 1 tsp baking powder
  • 0.25 tsp salt
  • 0.75 cup unsalted butter softened
  • 1 cup granulated sugar
  • 1 egg large
  • 1.5 tsp vanilla extract
  • 2 tbsp milk
Pineapple Topping
  • 0.5 cup brown sugar packed
  • 0.25 cup unsalted butter melted
  • 18 pineapple rounds small
  • 18 maraschino cherries drained

Equipment

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

Method
 

  1. Preheat oven to 350°F (175°C). Line baking sheets with parchment paper.
  2. Whisk flour, baking powder, and salt together in a bowl.
  3. Cream butter and sugar until light and fluffy. Add egg and vanilla and mix well.
  4. Gradually add dry ingredients and milk, mixing until a soft dough forms.
  5. Mix melted butter and brown sugar. Spoon small circles onto parchment.
  6. Place pineapple pieces and cherries on caramel circles.
  7. Scoop dough over fruit and flatten slightly.
  8. Bake 13–15 minutes until lightly golden. Cool 5 minutes then invert onto rack.

Notes

Drain pineapple well and flip cookies while warm for best release.