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Pineapple Upside Sugar Cookies Recipe

Pineapple Upside Sugar Cookies Recipe

5 Stars 4 Stars 3 Stars 2 Stars 1 Star 4.7 from 29 reviews
  • Author: Kimberly
  • Prep Time: 20 minutes
  • Cook Time: 14 minutes
  • Total Time: 34 minutes
  • Yield: 12 cookies
  • Category: Dessert
  • Method: Baking
  • Cuisine: American
  • Diet: Vegetarian

Description

Indulge in a delightful twist on traditional pineapple upside-down cake with these Pineapple Upside Sugar Cookies. These sweet treats feature a buttery cookie base topped with a pineapple ring, a maraschino cherry, and a brown sugar glaze.


Ingredients

For the Cookie Dough:

  • 1 cup unsalted butter (softened)
  • 1 cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 2¼ cups all-purpose flour
  • ½ teaspoon baking soda
  • ½ teaspoon baking powder
  • ¼ teaspoon salt

For Topping:

  • ½ cup crushed pineapple (well drained)
  • 12 maraschino cherries (halved)
  • ¼ cup brown sugar
  • 2 tablespoons melted butter

Instructions

  1. Prepare the Topping: Preheat oven to 350°F (175°C). Grease a muffin tin and combine brown sugar with melted butter. Spoon mixture into 12 cups, add a cherry half and pineapple.
  2. Make the Cookie Dough: Cream butter and sugar, then mix in egg and vanilla. Combine dry ingredients separately and gradually add to wet mixture.
  3. Assemble and Bake: Form dough into balls, flatten, and place over toppings. Bake for 12–14 minutes until golden. Cool, then invert onto a rack.

Notes

  • Thoroughly drain pineapple to prevent sogginess.
  • Best served fresh but can be stored for up to 2 days in an airtight container.