Pineapple Upside Down Cookies

A fun, dairy free treat, these pineapple upside down cookies are perfect for Easter and all of your spring festivities.

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.

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.

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.

Top these cookies with a dairy free pineapple frosting, recipe here.

Pineapple Upside Down Cookies
Prep Time
Cook Time
Total Time
Recipe Type: Baking
Serves: 30 cookies
  • Click the link above for the recipe.
  • 2½ cups all-purpose flour
  • 1½ teaspoons baking powder
  • ¼ teaspoon baking soda
  • ¼ teaspoon coarse salt
  • ½ cup shortening
  • 1 cup packed brown sugar
  • 1 egg
  • 1 teaspoon vanilla extract
  • ⅔ cup crushed pineapple (juices drained, but reserved)
For garnish:
  • Maraschino cherries
  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 ½ cup at at time, until incorporated, scraping sides as needed.
  6. Scoop dough with a medium cooking scoop onto parchment paper (with about 1½ 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.
  1. Click the link above for the recipe.
  2. Frost each cookie with a generous portion of frosting and top with a maraschino cherry.


Melissa Belanger

Melissa is a traveling hockey wife, mom and full time blogger, currently living in France. She is the author of the food blog A Teaspoon of Happiness and personal blog Love in a Suitcase. When she’s not developing recipes in the kitchen, she spends her days searching for the best French cuisine her town has to offer, cheering on her husband’s hockey team and enjoying life as a new mom.

More Posts - Website - Twitter - Facebook - Pinterest - Google Plus

No Comments Yet

Leave a Reply

Your email address will not be published.

Rate Recipe: