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Desserts

Upside Down Pineapple Cookies

Inspired by pineapple upside down cake, these upside down pineapple cookies aren’t really upside down. They are loaded with pineapple bits, laced with brown sugar and topped with a maraschino cherry. They taste just like everyone’s favorite retro dessert.

Pineapple cookies topped with pineapple frosting and maraschino cherries

Somethings really are happy accidents. I had literally no intention of making these cookies, and I certainly didn’t know they would turn out so well. But, these upside down pineapple cookies were the best surprise. when Ellie asked to make pineapple cookies because we had a fresh one sitting on our counter, I thought it would be a great way to use up that can of crushed pineapple that had been sitting in my pantry for ages.

For some reason, pineapple always reminds me of Easter – probably because of my favorite pineapple stuffing, and it’s perfect for this time of year when we’re starting to think about warmer weather. And these pineapple cookies would make a great addition to your Easter brunch or dessert for your Easter dinner.

Pineapple cookies topped with pineapple frosting and maraschino cherries

Why didn’t I use the fresh pineapple? For several reasons, but mostly because these pineapple cookies just didn’t need it. I didn’t want to waste my fresh pineapple, which I could enjoy as a snack on its own, when I would be baking the cookies and covering them with sugar. Plus, we always used canned pineapple to make my inspiration cake.

Normally, pineapple upside down cake is drenched in brown sugar and butter, but I made it dairy free by using butter-flavored shortening and I used brown sugar in the cookies and the frosting to make sure the flavors came through.

Pineapple cookies topped with pineapple frosting and maraschino cherries

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To make these dairy free upside down pineapple cookies you’ll need:

  • Baking basics, such as all-purpose flour, sugar, vanilla extract, egg, baking powder, etc.
  • Butter-flavored shortening (one of my favorite dairy free substitutes)
  • 1 can crushed pineapple
  • Maraschino cherries

You’ll also need parchment paper *affiliate link (or a silicone baking mat), an electric mixer *affiliate link and a pastry bag with a piping tip. I used this star one from this set.

Pineapple cookies topped with pineapple frosting and maraschino cherries

How to make upside down pineapple cookies:

To make these pineapple cookies, I added drained, crushed pineapple and brown sugar to a basic drop cookie.  Then I used the reserved pineapple juice from the can to my usual dairy free “buttercream” frosting, which I piped into the cookies and topped with a maraschino cherry.

You can obviously skip the cherries if you want, but I think they are a nice because they tie in the pineapple upside down cake idea, and they make them look pretty. Do what you want though.

Pineapple cookies topped with pineapple frosting and maraschino cherries

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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

Ingredients

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


Instructions

For the cookies:

  1. Preheat oven to 350˚F and line a baking sheet *affiliate link with parchment paper *affiliate link.
  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 *affiliate link, 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 *affiliate link (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.

If you like these pineapple cookies, you might also like these other pineapple recipes:

  • Reply
    Kristen Chidsey
    February 21, 2018 at 2:02 pm

    Such a fun cookie Melissa!! My son who adores pineapple updside down cake would love these. We will have to give them a try!

    • Reply
      Melissa Belanger
      February 21, 2018 at 6:30 pm

      Thanks! They were really fun to make (and eat :))

  • Reply
    Renee Fuentes
    February 26, 2018 at 10:59 am

    I’m so happy I found your blog! I recently had to go Dairy free due to my hormonal acne, and I was feeling so deprived, but now I see there’s lots of alternatives available!

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