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+ servings

Pineapple Upside Down Cookies

These Pineapple Upside Down Cookies are a delightful twist on the classic cake, featuring a chewy cookie base topped with caramelized pineapple and a maraschino cherry.
Prep : 10 Total : 25 minutes

Ingredients
  

Cookie Dough

  • 1 cup unsalted butter softened
  • 1.5 cup granulated sugar
  • 2 large eggs
  • 1 teaspoon vanilla extract
  • 2.5 cup all-purpose flour
  • 1 teaspoon baking soda
  • 0.5 teaspoon salt

Pineapple Topping

  • 1 can crushed pineapple drained well
  • 0.5 cup packed brown sugar
  • 0.25 cup unsalted butter melted
  • 24 maraschino cherries stems removed

Instructions
 

Preparation Steps

  • Preheat oven to 375°F (190°C). Line baking sheets with parchment paper.
  • In a large bowl, cream together the softened butter and granulated sugar until light and fluffy.
    1 cup unsalted butter
  • Beat in the eggs one at a time, then stir in the vanilla extract.
    1 cup unsalted butter
  • In a separate medium bowl, whisk together the flour, baking soda, and salt.
    1 cup unsalted butter
  • Gradually add the dry ingredients to the wet ingredients, mixing until just combined. Do not overmix.
  • In a small bowl, combine the drained crushed pineapple, brown sugar, and melted butter. Stir until well mixed.
    1 cup unsalted butter
  • Drop rounded tablespoons of cookie dough onto the prepared baking sheets.
  • Place a spoonful of the pineapple mixture on top of each cookie dough ball.
  • Gently press a maraschino cherry into the center of the pineapple mixture on each cookie.
    1 cup unsalted butter
  • Bake for 10-13 minutes, or until the edges are golden brown and the center is set.
  • Let the cookies cool on the baking sheets for a few minutes before transferring them to a wire rack to cool completely.

Notes

Store cooled cookies in an airtight container at room temperature for up to 3 days.