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Pineapple Upside-Down Sugar Cookies Recipe

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  • Author: Lidia
  • Prep Time: 20 minutes
  • Cook Time: 16 minutes
  • Total Time: 36 minutes
  • Yield: 12 cookies
  • Category: Dessert
  • Method: Baking
  • Cuisine: American
  • Diet: Vegetarian

Description

Soft and buttery sugar cookies topped with caramelized pineapple and cherries, inspired by the classic pineapple upside-down cake. These tropical cookies are sweet, fruity, and perfect for parties or everyday treats.


Ingredients

  • 1/4 cup unsalted butter, melted
  • 1/2 cup brown sugar
  • 6 pineapple rings, cut into small pieces
  • 6 maraschino cherries, halved
  • 2 1/2 cups all-purpose flour
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon salt
  • 3/4 cup unsalted butter, softened
  • 1 cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 2 tablespoons pineapple juice

Instructions

  1. Preheat the oven to 350°F (175°C) and lightly grease a muffin-top pan or line a baking sheet with parchment paper.
  2. In a small bowl, mix the melted butter and brown sugar together. Spoon a small amount into each cookie space or onto small circles on the prepared baking sheet.
  3. Arrange pineapple pieces over the brown sugar mixture and place half a maraschino cherry in the center of each.
  4. In a medium bowl, whisk together the flour, baking powder, and salt.
  5. In a large bowl, beat the softened butter and granulated sugar until light and fluffy.
  6. Mix in the egg, vanilla extract, and pineapple juice until smooth.
  7. Gradually add the dry ingredients to the wet ingredients and stir until a soft dough forms.
  8. Scoop portions of dough over the pineapple topping and gently spread to cover the fruit.
  9. Bake for 14 to 16 minutes, or until the edges are lightly golden.
  10. Allow the cookies to cool for 5 minutes before carefully turning them upside down onto a cooling rack.

Notes

  • Drain canned pineapple well before using to avoid excess moisture.
  • Store cookies in an airtight container in the refrigerator for up to 4 days.
  • Place parchment paper between cookie layers to prevent sticking.
  • Microwave each cookie for about 10 seconds before serving for a warm caramelized topping.
  • For extra tropical flavor, add shredded coconut to the topping.
  • A light vanilla glaze can be drizzled over cooled cookies for added sweetness.
  • The cookie dough can be prepared a day ahead and refrigerated until ready to bake.

Nutrition

  • Serving Size: 1 cookie
  • Calories: 260
  • Sugar: 21g
  • Sodium: 95mg
  • Fat: 11g
  • Saturated Fat: 7g
  • Unsaturated Fat: 3g
  • Trans Fat: 0g
  • Carbohydrates: 38g
  • Fiber: 1g
  • Protein: 3g
  • Cholesterol: 38mg