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Pineapple Upside-Down Cookies Recipe

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★★★★★

4.6 from 126 reviews

These Pineapple Upside-Down Cookies combine the tropical sweetness of pineapple and maraschino cherries with a rich, buttery cookie base. Featuring a caramelized brown sugar topping that gives the cookies a delightful upside-down effect, this recipe is perfect for a tropical twist on classic cookies that are tender, flavorful, and visually appealing.

Ingredients

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Cookie Dough

  • ½ cup unsalted butter, softened
  • ¾ cup granulated sugar
  • 1 large egg
  • 1 tsp vanilla extract
  • 1 ¼ cups all-purpose flour
  • ½ tsp baking powder
  • ¼ tsp salt

Caramelized Topping

  • ½ cup brown sugar
  • 2 tbsp melted butter
  • 1 small can pineapple rings, cut into smaller pieces
  • Maraschino cherries, halved

Instructions

  1. Prepare the caramelized base: In a small bowl, combine the brown sugar and melted butter until well blended. Press this mixture evenly into the bottom of your cookie baking pan or muffin tins to form the caramelized base.
  2. Arrange the fruit: Place cut pineapple pieces evenly over the brown sugar mixture. Add halved maraschino cherries atop the pineapple to add color and a burst of sweetness.
  3. Make the cookie dough: In a mixing bowl, cream the softened unsalted butter and granulated sugar until light and fluffy. Beat in the egg and vanilla extract until fully incorporated.
  4. Combine dry ingredients: In a separate bowl, whisk together the all-purpose flour, baking powder, and salt to evenly distribute the leavening agents and salt.
  5. Mix dry into wet: Gradually add the dry ingredients to the wet batter, mixing until just combined to avoid overworking the dough, which can make the cookies tough.
  6. Assemble and bake: Gently drop or spoon the cookie dough over the fruit and caramel base, spreading lightly to cover. Bake the cookies in a preheated oven at 350°F (175°C) for 18-22 minutes or until the cookies are golden and set.
  7. Cool and invert: Allow the cookies to cool for about 10 minutes. Carefully invert the pan onto a cooling rack so the caramelized pineapple and cherry topping are exposed on top, revealing the classic upside-down look.
  8. Serve and enjoy: Let the cookies cool completely before serving. These cookies pair beautifully with a cup of tea or as a sweet treat any time of the day.

Notes

  • For a gluten-free version, substitute the all-purpose flour with a 1:1 gluten-free baking flour.
  • If allergic to eggs, replace the egg with a flax egg (1 tbsp ground flaxseed mixed with 3 tbsp water, let sit for 5 minutes to thicken).
  • Fresh pineapple can be used instead of canned, but cut it into small pieces to ensure even baking.
  • Brown sugar in the topping creates the signature caramelized effect; do not substitute with white sugar.
  • Use salted butter but reduce added salt in the dough to ⅛ tsp to avoid over-salting.
  • Handle the inversion step gently to prevent the cookies from breaking apart.

Keywords: pineapple cookies, upside-down cookies, tropical cookies, caramelized cookies, pineapple dessert

Find it online: https://spatulaqueen.com/pineapple-upside-down-cookies-recipe/