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Pineapple Upside Down Sugar Cookies

These Pineapple Upside Down Sugar Cookies combine the nostalgic flavors of a classic pineapple upside down cake with a soft, buttery sugar cookie base. With a caramelized topping, juicy pineapple halves, and a sweet maraschino cherry center, these bite-sized treats are both eye-catching and delicious. Perfect for gatherings or a personal treat, they’re sure to delight anyone who loves a creative twist on traditional desserts.
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Prep Time 15 minutes
Cook Time 18 minutes
Total Time 38 minutes
Servings: 12 cookies
Course: Dessert
Cuisine: American
Ingredients Equipment Method Notes

Ingredients
  

Topping
  • 1/4 cup unsalted butter melted
  • 1/2 cup packed light brown sugar
  • 12 pineapple rings each cut into halves (canned or fresh)
  • 24 maraschino cherries drained
Sugar Cookie Base
  • 1 cup unsalted butter softened
  • 1 cup granulated sugar
  • 1 large egg
  • 1 teaspoon pure vanilla bean paste
  • 2 1/4 cups all-purpose flour
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon baking soda
  • 1/4 teaspoon salt
  • 2 tablespoons pineapple juice from the canned pineapple or fresh

Equipment

  • Two 12-cup muffin tins
  • Large mixing bowl
  • Small bowl
  • Wire rack

Method
 

  1. Preheat your oven to 350°F. Grease or line two 12-cup muffin tins to ensure the cookies release easily once baked.
  2. For the topping, combine 1/4 cup melted unsalted butter with 1/2 cup packed light brown sugar in a small bowl until well mixed. Spoon about 1 teaspoon of this caramel mixture into the bottom of each muffin cup, then arrange a halved pineapple ring in each cup and place a maraschino cherry in the center.
  3. In a large bowl, cream together 1 cup softened unsalted butter and 1 cup granulated sugar until light and fluffy (about 2 minutes). Beat in the egg, 1 teaspoon vanilla bean paste, and 2 tablespoons pineapple juice until well combined.
  4. In a separate bowl, whisk together 2¼ cups all-purpose flour, ½ teaspoon baking powder, ¼ teaspoon baking soda, and ¼ teaspoon salt. Gradually add the dry ingredients to the wet mixture, mixing just until incorporated to keep the cookies tender.
  5. Scoop the cookie dough evenly over the prepared topping in each muffin cup, filling each about 2/3 full. The dough will spread as it bakes, so avoid overfilling.
  6. Bake for approximately 15-18 minutes, or until the edges are golden brown and the centers are set. The transformation of the caramelized topping is part of the magic!
  7. Allow the cookies to cool in the pan for about 5 minutes, then carefully invert them onto a wire rack to cool completely.

Notes

These Pineapple Upside Down Sugar Cookies are a playful twist on a classic dessert. The bite-sized cookies offer the captivating flavors of caramelized pineapple and cherries atop a soft sugar cookie, making them perfect for parties and casual gatherings. You can easily swap ingredients like using peach slices or a splash of rum for a boozy version, and they store well in an airtight container for a couple of days.