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Pineapple Upside Down Sugar Cookies

Soft buttery sugar cookies topped with caramelized pineapple and cherries inspired by classic pineapple upside-down cake.
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Prep Time 20 minutes
Cook Time 15 minutes
Total Time 35 minutes
Servings: 16 cookies
Course: Dessert
Cuisine: American, Tropical
Calories: 210
Ingredients Equipment Method Notes

Ingredients
  

Cookie Dough
  • 2.25 cups all-purpose flour
  • 1 tsp baking powder
  • 0.5 tsp salt
  • 0.75 cup unsalted butter softened
  • 0.75 cup granulated sugar
  • 1 egg large
  • 2 tsp vanilla extract
  • 2 tbsp milk
Topping
  • 0.25 cup unsalted butter melted
  • 0.5 cup brown sugar
  • 8 pineapple rings drained and chopped
  • 16 maraschino cherries halved

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. Whisk flour, baking powder, and salt together in a bowl.
  3. Cream butter and sugar until light and fluffy.
  4. Add egg and vanilla extract and mix well.
  5. Mix dry ingredients into the wet ingredients and add milk until dough forms.
  6. Mix melted butter and brown sugar to create topping mixture.
  7. Place small spoonfuls of topping mixture on baking sheet, add pineapple pieces and cherries.
  8. Scoop cookie dough over toppings and bake for 12–15 minutes.
  9. Cool slightly then flip cookies so pineapple topping faces up.

Notes

Drain pineapple well to prevent soggy cookies.