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Pineapple Upside-Down Sugar Cookies

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  • Author: KimEasy

Description

Pineapple Upside-Down Sugar Cookies combine the classic flavors of pineapple upside-down cake with the simplicity of sugar cookies. These delightful treats feature a soft, buttery cookie base topped with caramelized pineapple slices and maraschino cherries, making them perfect for any occasion.


Ingredients

Units Scale

For the Topping:

  • 6 tablespoons unsalted butter, melted
  • 1 cup brown sugar
  • 12 canned pineapple rings, drained
  • 12 maraschino cherries, drained

For the Cookie Dough:

  • 1/2 cup unsalted butter, softened
  • 1/2 cup granulated sugar (100g)
  • 1/2 cup powdered sugar (65g)
  • 1/4 cup vegetable oil
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 2 cups all-purpose flour (240g)
  • 1/2 teaspoon baking soda
  • 1/2 teaspoon cream of tartar
  • 1/2 teaspoon salt

Instructions

  1. Prepare the Topping:
    • Preheat your oven to 350ยฐF (175ยฐC).
    • In a bowl, combine the melted butter and brown sugar.
    • Evenly distribute about 1 tablespoon of this mixture into each well of a non-stick muffin top pan or a standard muffin tin.
    • Place a drained pineapple ring on top of the brown sugar mixture in each well.
    • Center a maraschino cherry in the middle of each pineapple ring.
  2. Make the Cookie Dough:
    • In a large mixing bowl, cream together the softened butter and granulated sugar until light and fluffy.
    • Add the powdered sugar and mix until well combined.
    • Pour in the vegetable oil, egg, and vanilla extract; mix until smooth.
    • In a separate bowl, whisk together the flour, baking soda, cream of tartar, and salt.
    • Gradually add the dry ingredients to the wet mixture, mixing until a soft dough forms.
  3. Assemble the Cookies:
    • Scoop about 3 tablespoons of cookie dough and flatten it slightly.
    • Place the flattened dough over the pineapple and cherry in each muffin well, gently pressing to cover the fruit and sealing the edges.
  4. Bake:
    • Bake in the preheated oven for 8-10 minutes, or until the edges are lightly golden and the centers are set.
    • Remove from the oven and allow the cookies to cool in the pan for about 10 minutes.
  5. Invert and Serve:
    • Carefully invert the pan onto a parchment-lined baking sheet or cooling rack. The cookies should release easily, showcasing the caramelized pineapple and cherry topping.
    • Allow the cookies to cool completely before serving.

Notes

  • Using a non-stick muffin top pan is recommended for best results.
  • Ensure the pineapple rings and cherries are well-drained to prevent excess moisture.
  • These cookies are best enjoyed fresh but can be stored in an airtight container at room temperature for up to 2 days.