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Pineapple Upside Down Sugar Cookies


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  • Author: Amelia Sinclair
  • Total Time: 45 minutes
  • Yield: 13 cookies 1x
  • Diet: Vegetarian

Description

Delicious Pineapple Upside Down Sugar Cookies that combine the classic flavors of pineapple upside down cake with a chewy sugar cookie base.


Ingredients

Scale
  • 1 cup unsalted butter, at room temperature
  • 1 1/2 cups granulated sugar
  • 2 large eggs
  • 2 teaspoons vanilla extract
  • 1/2 cup sour cream
  • 3 cups all-purpose flour
  • 1 teaspoon baking powder
  • 1 teaspoon cornstarch
  • 1/2 teaspoon salt
  • 13 canned pineapple slices, drained
  • 13 maraschino cherries
  • 1/2 cup unsalted butter, melted
  • 1 cup light brown sugar, packed

Instructions

  1. Preheat the oven to 350°F (175°C) and grease a mini round cake pan or muffin tin.
  2. In a large mixing bowl, cream together room temperature butter and granulated sugar with an electric mixer until light and fluffy.
  3. Add eggs, vanilla extract, and sour cream to the creamed mixture. Mix until fully integrated.
  4. In a separate bowl, whisk together all-purpose flour, baking powder, cornstarch, and salt.
  5. Gradually add dry ingredients into the wet mixture, mixing until just combined. Set dough aside.
  6. In another bowl, blend melted butter and light brown sugar until smooth to create the brown sugar glaze.
  7. Spoon about 1 tablespoon of the brown sugar mixture into each cavity of the prepared pan, spreading evenly.
  8. Place a pineapple slice over the brown sugar glaze and position a maraschino cherry in the center of each pineapple ring.
  9. Using a 3-tablespoon scoop, portion cookie dough over each fruit-topped cavity and gently flatten the dough with an offset spatula.
  10. Bake for 25 minutes, or until the cookies are golden around the edges and the brown sugar is bubbling up the sides.
  11. Cool for 10 minutes, then carefully invert cookies onto wax paper to allow brown sugar glaze to run over the tops.
  12. Allow cookies to cool completely before serving and store in an airtight container.

Notes

  • For best results, use fresh pineapple if available.
  • Store cookies in an airtight container to maintain freshness.
  • These cookies can be served warm or at room temperature.
  • Prep Time: 20 minutes
  • Cook Time: 25 minutes
  • Category: Dessert
  • Method: Baking
  • Cuisine: American

Nutrition

  • Serving Size: 1 cookie
  • Calories: 200
  • Sugar: 15g
  • Sodium: 150mg
  • Fat: 8g
  • Saturated Fat: 5g
  • Unsaturated Fat: 3g
  • Trans Fat: 0g
  • Carbohydrates: 30g
  • Fiber: 1g
  • Protein: 2g
  • Cholesterol: 30mg