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Pineapple Upside Down Cookies Recipe

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4 from 13 reviews

Delight in these charming Pineapple Upside Down Cookies featuring a sweet and buttery brown sugar and pineapple base topped with soft, fluffy cookie dough. Perfectly baked until golden with a maraschino cherry center, these bite-sized treats combine the nostalgic flavors of pineapple upside down cake with the convenience of cookies.

Ingredients

Brown Sugar Pineapple Base

  • 6 tablespoons Butter, melted
  • 1 cup Brown Sugar (214g)
  • Pineapple Rings, drained
  • Maraschino Cherries, drained

Cookie Dough

  • ½ cup Butter, softened
  • ½ cup Granulated Sugar (100g)
  • 1 large Egg
  • 1 teaspoon Vanilla Extract
  • ½ cup Powdered Sugar (65g)
  • ¼ cup Vegetable Oil
  • 2 cups All Purpose Flour (240g)
  • ½ teaspoon Baking Soda
  • ½ teaspoon Cream of Tartar

Instructions

  1. Pan Preparations: Preheat the oven to 350°F (175°C). In a small mixing bowl, combine the melted butter with brown sugar and mix until combined. Drain the pineapple rings and set aside. Spoon 1 tablespoon of the butter and brown sugar mixture into each well of a muffin tin, topping each with one pineapple ring and placing a maraschino cherry in the center of each ring. Arrange the muffin tin so cookies have space to spread without touching.
  2. Prepare Cookie Dough: In a large bowl, cream the softened butter and granulated sugar together until light and fluffy, scraping the sides of the bowl as needed. Add the egg and vanilla extract, continuing to cream for 2-3 minutes until well combined.
  3. Incorporate Remaining Ingredients: Gradually add the vegetable oil and powdered sugar to the butter mixture, beating until the mixture turns pale yellow and fully combined. Stir in the all-purpose flour, baking soda, and cream of tartar, mixing until just combined to form the cookie dough.
  4. Assemble Cookies: Using a #24 cookie scoop, portion the dough and press each ball flat in the palm of your hand to about 3 inches in diameter. Place each flattened dough piece on top of the pineapple ring and cherry in the muffin tin, carefully tucking the edges into the sides of the well to seal the cookie dough around the fruit base.
  5. Bake: Bake the cookies in the preheated oven for 8-10 minutes, or until the edges are lightly golden and the center is no longer glossy.
  6. Invert and Cool: Remove the muffin tin from the oven and immediately invert it onto a parchment-lined baking sheet. The cookies will pop out to reveal the classic upside down pineapple appearance. Allow the cookies to cool completely before serving.

Notes

  • Ensure the pineapple rings are well drained to prevent soggy cookies.
  • Stagger the cookies in the muffin tin to allow space for spreading.
  • Use a cookie scoop for uniform cookie size.
  • Be careful when inverting the pan after baking to avoid breaking the delicate cookies.
  • Cooling the cookies completely helps to firm up the butter and sugar topping.

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