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A plate of pineapple upside down sugar cookies topped with maraschino cherries and pineapple chunks.

Pineapple Upside Down Sugar Cookies


  • Author: Chef Clara
  • Total Time: 35 minutes
  • Yield: 12 cookies
  • Diet: Vegetarian

Description

Sweet and buttery pineapple upside down sugar cookies with caramelized fruit topping—perfect for tropical dessert lovers and party treats.


Ingredients

Scale
  • 1/2 cup unsalted butter, softened
  • 1 cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 2 cups all-purpose flour
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon salt
  • 1/4 cup unsalted butter, melted
  • 1/2 cup brown sugar
  • 12 maraschino cherries
  • 1 cup pineapple tidbits, well-drained


Instructions

  1. Preheat oven to 350°F (175°C). Grease a 12-cup muffin tin.
  2. In a small bowl, mix melted butter and brown sugar. Spoon about 1 teaspoon of the mixture into each muffin cup.
  3. Place one maraschino cherry in the center of each cup, then add a few pineapple tidbits around the cherry.
  4. In a large bowl, cream together softened butter and granulated sugar until light and fluffy.
  5. Beat in the egg and vanilla extract until combined.
  6. In a separate bowl, whisk together flour, baking powder, and salt. Gradually add the dry ingredients to the wet mixture and mix until a dough forms.
  7. Roll dough into 12 equal balls and flatten slightly. Place each piece of dough on top of the fruit mixture in the muffin cups.
  8. Bake for 18–22 minutes, or until the edges are golden.
  9. Let cool in the pan for 5–10 minutes. Run a knife around the edges and carefully invert onto a wire rack or tray while still warm.
  10. Serve warm or cooled.

Notes

  • Ensure pineapple is well-drained to avoid soggy bottoms.
  • Use silicone muffin pans for easier release.
  • Serve with a scoop of vanilla ice cream for an indulgent treat.
  • Prep Time: 15 minutes
  • Cook Time: 20 minutes
  • Category: Dessert
  • Method: Baking
  • Cuisine: American

Nutrition

  • Serving Size: 1 cookie
  • Calories: 210
  • Sugar: 18g
  • Sodium: 70mg
  • Fat: 10g
  • Saturated Fat: 6g
  • Unsaturated Fat: 3g
  • Trans Fat: 0g
  • Carbohydrates: 28g
  • Fiber: 0g
  • Protein: 2g
  • Cholesterol: 30mg