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Pineapple Upside Down Sugar Cookies

Tropical sugar cookies topped with caramelized pineapple and maraschino cherries for a fun and festive dessert.
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Prep Time 20 minutes
Cook Time 15 minutes
Total Time 35 minutes
Servings: 12 cookies
Course: Dessert, Snack
Cuisine: American, Tropical
Calories: 190

Ingredients
  

Cookie Dough
  • 2.5 cups all-purpose flour
  • 1 tsp baking powder
  • 0.5 tsp salt
  • 0.75 cup unsalted butter softened
  • 1 cup granulated sugar
  • 2 eggs large
  • 2 tsp vanilla extract
Topping
  • 0.5 cup brown sugar packed
  • 4 tbsp unsalted butter melted
  • 0.5 cup pineapple chunks fresh or canned
  • 12 maraschino cherries halved

Equipment

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

Method
 

  1. Preheat oven to 350°F (175°C). Line baking sheet with parchment paper.
  2. In medium bowl, whisk flour, baking powder, and salt.
  3. In large bowl, cream butter and sugar until fluffy. Add eggs one at a time, then vanilla.
  4. Gradually add dry ingredients to wet ingredients until dough forms.
  5. Mix brown sugar and melted butter for topping.
  6. Roll dough into 1.5-inch balls, flatten slightly, place on baking sheet. Press brown sugar mixture on top.
  7. Top each cookie with pineapple chunk and cherry half, pressing gently.
  8. Bake 12–15 minutes until edges are lightly golden. Cool on wire rack.

Notes

Drain pineapple well to avoid soggy cookies. Can sprinkle lightly with coconut for tropical twist.