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Pineapple Upside Down Cookie: A Delicious Twist on a Classic Dessert

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Soft, chewy cookies with caramelized pineapple and cherry topping, like pineapple upside-down cake.

Ingredients

Scale
  • 1/2 cup (1 stick) unsalted butter
  • 1 cup packed light brown sugar
  • 1 (20 ounce) can pineapple slices, drained well, juice reserved
  • Maraschino cherries, halved (optional, but highly recommended!)
  • 2 1/4 cups all-purpose flour
  • 1 teaspoon baking soda
  • 1 teaspoon ground cinnamon
  • 1/2 teaspoon salt
  • 1 cup (2 sticks) unsalted butter, softened
  • 3/4 cup granulated sugar
  • 3/4 cup packed light brown sugar
  • 2 large eggs
  • 1 teaspoon vanilla extract
  • 1/4 cup reserved pineapple juice (from the canned pineapple)

Instructions

  1. Prepare the Caramel Base: In a medium saucepan, melt the butter over medium heat. Stir in the brown sugar until completely dissolved and smooth (2-3 minutes). Simmer on low for 2-3 minutes, stirring occasionally.
  2. Line a large baking sheet with parchment paper. Spoon 1 tablespoon of caramel mixture onto the parchment paper for each cookie.
  3. Place a pineapple slice on top of each caramel dollop. Place a halved maraschino cherry in the center of each pineapple slice.
  4. Make the Cookie Dough: In a medium bowl, whisk together the flour, baking soda, cinnamon, and salt.
  5. In a large bowl (or stand mixer), cream together the softened butter, granulated sugar, and brown sugar until light and fluffy (3-5 minutes).
  6. Beat in the eggs one at a time, then stir in the vanilla extract.
  7. Stir in the reserved pineapple juice.
  8. Gradually add the dry ingredients to the wet ingredients, mixing until just combined. Do not overmix.
  9. Assemble and Bake: Drop rounded tablespoons of cookie dough onto each pineapple slice, spreading gently to cover.
  10. Bake in a preheated oven at 350°F (175°C) for 12-15 minutes, or until the edges are golden brown and the centers are set.
  11. Cool on the baking sheet for 5 minutes.
  12. Carefully invert the cookies onto a wire rack to cool completely.

Notes

  • Don’t overbake the cookies.
  • Use softened butter for the cookie dough.
  • Drain the pineapple slices well.
  • The caramel base and cookie dough can be made ahead of time.
  • Variations: Add shredded coconut, chopped nuts, or chocolate chips to the cookie dough. Add a pinch of ground ginger or nutmeg for a warm, spicy flavor.

Find it online: https://anasrecipes.com/pineapple-upside-down-cookie/