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Pineapple Upside Down Cookies Recipe

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4.1 from 15 reviews

These Pineapple Upside Down Cookies combine the classic flavors of the traditional cake in a fun and easy cookie form. Featuring a moist pineapple ring and cherry topping beneath a buttery, soft cookie, they’re baked to golden perfection and flipped to reveal a glossy caramelized fruit topping. Perfect for a unique dessert or sweet snack.

Ingredients

For the Topping

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

For the Cookie Dough

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

Instructions

  1. Pan Preparations: Preheat your oven to 350°F (175°C). In a small mixing bowl, combine the melted butter with the brown sugar, stirring until well mixed.
  2. Arrange Toppings: Drain the pineapple rings and place 1 tablespoon of the brown sugar and butter mixture into each well of a muffin tin. Place one pineapple ring on top of the mixture, then set a maraschino cherry in the center of each pineapple ring.
  3. Prepare Cookie Dough: In a mixing bowl, cream together the softened butter and granulated sugar until light and fluffy, scraping down the sides as needed. Add the egg and vanilla extract and continue to mix for 2-3 minutes to combine fully.
  4. Add Remaining Ingredients: Gradually mix in the vegetable oil and powdered sugar until the mixture becomes pale yellow and creamy. Next, sift in the flour, baking soda, and cream of tartar, mixing until just combined to form the dough.
  5. Shape Cookies: Using a #24 cookie scoop, portion the dough and flatten each ball in your palm to about 3 inches in diameter.
  6. Assemble Cookies: Carefully place each flattened dough piece on top of the pineapple ring and cherry in the muffin tin well. Tuck the edges of the dough down the sides of the well to seal the topping inside.
  7. Bake: Bake the cookies at 350°F (175°C) for 8-10 minutes, or until the edges turn lightly golden and the centers lose their glossy appearance.
  8. Flip and Cool: Remove the pan from the oven and immediately invert it onto a parchment-lined cookie sheet to release the cookies, showcasing the upside-down pineapple topping. Allow the cookies to cool completely before serving.

Notes

  • Ensure the pineapple rings and cherries are well drained to avoid soggy cookie bottoms.
  • Stagger cookies in the muffin tin to prevent them from spreading and touching during baking.
  • Press cookie dough flat carefully to properly cover the fruit and seal edges to avoid leaking during baking.
  • Use room temperature butter and egg for better creaming and dough consistency.
  • For added flavor, sprinkle a pinch of cinnamon or nutmeg in the dough if desired.

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