Pineapple cookies topped with pineapple frosting and maraschino cherries

Upside Down Pineapple Cookies

  • Author: Melissa Belanger
  • Prep Time: 20 minutes
  • Cook Time: 20 minutes
  • Total Time: 40 minutes
  • Yield: 30 cookies 1x


For the frosting:

  • 1/2 cup shortening
  • 2 1/2 cups confectioners’ or glazing sugar
  • Pinch of coarse salt
  • 4 tablespoons pineapple juice

For the cookies:

  • 2 1/2 cups all-purpose flour
  • 1 1/2 teaspoons baking powder
  • 1/4 teaspoon baking soda
  • 1/4 teaspoon coarse salt
  • 1/2 cup shortening
  • 1 cup packed brown sugar
  • 1 egg
  • 1 teaspoon vanilla extract
  • 2/3 cup crushed pineapple (juices drained, but reserved)

    For garnish:

Maraschino cherries


For the cookies:

  1. Preheat oven to 350˚F and line a baking sheet with parchment paper.
  2. In a large bowl, whisk together flour, baking powder, baking soda and salt. Set aside.
  3. In a large bowl with an electric mixer, cream shortening and brown sugar at medium speed until light and fluffy, about 2 minutes.
  4. Add egg, vanilla and pineapple. Continue to beat until incorporated.
  5. Add flour mixture, about 1/2 cup at at time, until incorporated, scraping sides as needed.
  6. Scoop dough with a medium cooking scoop onto parchment paper (with about 1 1/2 inches between cookies). Bake 15 – 18 minutes or until cookies are golden and tops are set.
  7. Remove from oven and allow cookies to rest for about 5 minutes before transferring to cooling rack.

For the frosting:

  1. In a large bowl with an electric mixture, beat together shortening, sugar, salt and 2 tablespoons pineapple juice until smooth. Add extra pineapple juice, as needed until desired consistency has been reached.
  2. Frost each cookie with a generous portion of frosting and top with a maraschino cherry.

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