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Pineapple Upside Down Sugar Cookies – Sweet, Buttery & Tropical-Inspired!

Pineapple Upside Down Sugar Cookies


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  • Author: Jennifer
  • Total Time: 40 minutes
  • Yield: 13 cookies 1x
  • Diet: Vegetarian

Description

A delightful twist on traditional sugar cookies, featuring a caramelized layer of pineapple and cherries on top.


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 oven to 350°F (175°C). 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 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. 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. 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. Store in an airtight container.

Notes

  • Ensure the butter is at room temperature for easier creaming with sugar.
  • Can substitute fresh pineapple for canned if desired.
  • Cookies can be stored in an airtight container for up to a week.
  • Prep Time: 15 minutes
  • Cook Time: 25 minutes
  • Category: Dessert
  • Method: Baking
  • Cuisine: American

Nutrition

  • Serving Size: 1 cookie
  • Calories: 180
  • Sugar: 15g
  • Sodium: 110mg
  • Fat: 7g
  • Saturated Fat: 4g
  • Unsaturated Fat: 2g
  • Trans Fat: 0g
  • Carbohydrates: 25g
  • Fiber: 1g
  • Protein: 2g
  • Cholesterol: 35mg