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Pineapple Upside‑Down Sugar Cookies

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These Pineapple Upside-Down Sugar Cookies combine the charm of classic pineapple upside-down cake with buttery sugar cookies. Each cookie features caramelized pineapple and a cherry topping baked beneath a soft, tender cookie base for a tropical treat that’s as beautiful as it is delicious.

  • Total Time: 40 minutes
  • Yield: 12–14 cookies

Ingredients

  • ½ cup unsalted butter, melted
  • 1 cup light brown sugar, packed
  • Pineapple slices (canned or fresh, well-drained)
  • Maraschino cherries
  • 1 cup unsalted butter, softened
  • 1½ cups granulated sugar
  • 2 large eggs
  • ½ cup sour cream
  • 3 cups all-purpose flour
  • 1 teaspoon baking powder
  • 1 teaspoon cornstarch
  • ½ teaspoon salt
  • 2 teaspoons vanilla extract

Instructions

  1. Preheat oven to 350°F (175°C). Grease a muffin tin or line it with parchment rounds.
  2. In a small bowl, combine melted butter and brown sugar. Spoon about 1 tablespoon into each muffin cup.
  3. Place a pineapple slice on top of the brown sugar mixture, and add a maraschino cherry in the center.
  4. In a large bowl, cream softened butter and granulated sugar until light and fluffy.
  5. Add eggs one at a time, mixing well after each addition. Stir in sour cream and vanilla extract.
  6. In a separate bowl, whisk together flour, baking powder, cornstarch, and salt.
  7. Gradually add dry ingredients to the wet mixture, mixing just until combined.
  8. Scoop about 2 tablespoons of dough, flatten slightly, and press it over the fruit layer in each muffin cup.
  9. Bake for 12–15 minutes, or until edges are lightly golden.
  10. Cool in the pan for 10 minutes, then carefully invert the tin onto a cooling rack or parchment paper to release the cookies fruit-side up.
  11. Let cool completely before serving.

Notes

  • Use fresh pineapple for a bolder flavor and less sweetness.
  • Substitute sour cream with plain yogurt or buttermilk if needed.
  • Add cinnamon or ginger to the dough for extra warmth.
  • Try chopped pineapple for a different look and texture.
  • Drizzle with melted white chocolate once cooled for a sweet finish.
  • Cool for 10 minutes before flipping to prevent breakage.
  • Author: Amelia
  • Prep Time: 20 minutes
  • Cook Time: 15 minutes
  • Category: Dessert
  • Method: Baking
  • Cuisine: American
  • Diet: Vegetarian

Nutrition

  • Serving Size: 1 cookie
  • Calories: 220
  • Sugar: 22 g
  • Sodium: 95 mg
  • Fat: 10 g
  • Saturated Fat: 6 g
  • Unsaturated Fat: 4 g
  • Trans Fat: 0 g
  • Carbohydrates: 30 g
  • Fiber: 0 g
  • Protein: 2 g
  • Cholesterol: 45 mg