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–+ servings
Delicious pineapple upside-down cookies on a baking sheet ready to enjoy

Pineapple Upside-Down Sugar Cookies

These cookies capture the classic flavors of pineapple upside-down cake in a handheld cookie format with a buttery finish and caramelized topping.
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Prep Time 25 minutes
Cook Time 15 minutes
Total Time 45 minutes
Servings: 12 cookies
Course: Dessert, Snack
Cuisine: American
Calories: 180
Ingredients Method Nutrition Notes

Ingredients
  

Cookie Base
  • 1/2 cup unsalted butter, melted
  • 1/2 cup packed brown sugar Can use light or dark brown sugar.
  • 1 can (20 oz) pineapple slices, drained and cut into small pieces Crushed canned pineapple pieces can also be used.
  • 1 Maraschino cherries, halved
Cookie Dough
  • 1 cup unsalted butter, softened
  • 1 cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 2 1/2 cups all-purpose flour
  • 1 teaspoon baking powder
  • 1/4 teaspoon salt

Method
 

Preparation
  1. Preheat the oven to 350°F (175°C) and grease or line a muffin tin with parchment rounds.
  2. In a small bowl, stir together melted butter and brown sugar until combined, then spoon about 1 tablespoon into each muffin cup.
  3. Place pineapple pieces on top of the brown sugar mixture, arranging them fully to cover, then press a halved maraschino cherry into the center of each.
  4. In a large bowl, cream softened butter and granulated sugar until lighter in color and slightly increased in volume.
  5. Beat in the egg and vanilla extract until smooth.
  6. In a separate bowl, whisk together flour, baking powder, and salt. Gradually add to the wet ingredients and mix to form a soft dough.
  7. Take 1 1/2 tablespoons of dough and press it over the fruit in each muffin cup, smoothing to seal.
Baking
  1. Bake for 12 to 15 minutes, watching for cookie edges to turn lightly golden.

Nutrition

Serving: 1Calories: 180kcalCarbohydrates: 26gProtein: 2gFat: 8gSaturated Fat: 5gSodium: 100mgSugar: 12g

Notes

Chill dough for 10-15 minutes if too soft. Store cookies in the fridge layered with parchment for up to 4 days or freeze for up to 2 months. Reheat in a 325°F (163°C) oven or microwave briefly.

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