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Pineapple Upside Down Sugar Cookies

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These delightful cookies combine the classic flavors of pineapple upside down cake with soft sugar cookies. Each bite-sized treat features a caramelized pineapple and cherry topping on a buttery cookie base, creating the perfect portable version of the beloved dessert.
Prep Time 20 minutes
Cook Time 18 minutes
Total Time 38 minutes
Servings: 24 cookies
Course: Dessert
Cuisine: American

Ingredients
  

For the Topping
  • 1/4 cup unsalted butter melted
  • 1/2 cup light brown sugar packed
  • 12 pineapple rings cut into halves (canned or fresh)
  • 24 maraschino cherries drained
For the Sugar Cookie Base
  • 1 cup unsalted butter softened
  • 1 cup granulated sugar
  • 1 large egg
  • 1 teaspoon 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 canned pineapple or fresh

Equipment

  • 2 12-cup muffin tins
  • Mixing bowls
  • Electric mixer
  • Wire cooling rack

Method
 

  1. Preheat oven to 350°F and lightly grease or line two 12-cup muffin tins.
  2. Combine melted butter with brown sugar in a small bowl until well mixed. Spoon about 1 teaspoon of this caramel mixture into the bottom of each muffin cup.
  3. Arrange a halved pineapple ring over the sugar mixture in each cup, then place a maraschino cherry in the center.
  4. In a large bowl, cream together softened butter and granulated sugar until light and fluffy (about 2 minutes).
  5. Beat in the egg, vanilla bean paste, and pineapple juice until completely combined.
  6. In a separate bowl, whisk together flour, baking powder, baking soda, and salt.
  7. Gradually add dry ingredients to wet ingredients, mixing just until incorporated.
  8. Scoop cookie dough over each prepared pineapple and cherry arrangement, filling muffin cups about ⅔ full.
  9. Bake for 15-18 minutes, or until edges are golden brown and centers are set.
  10. Cool in the pan for 5 minutes before carefully inverting onto a wire rack to cool completely.

Notes

You can substitute vanilla extract for vanilla bean paste if needed. While canned pineapple works perfectly, fresh pineapple can be used for brighter flavor. If using fresh pineapple, make sure to purchase separate pineapple juice for the cookie dough. Store cookies in an airtight container for up to 3 days. For a variation, try using peach slices or mango chunks instead of pineapple, or add a splash of rum to the brown sugar mixture for an adult version.

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