Upside Down Pineapple Cookies
These upside down pineapple cookies are loaded with pineapple bits, laced with brown sugar and topped with a maraschino cherry.
Why you’ll love these pineapple upside down cookies
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.
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.
If you like this recipe, you have to try these banana bread cookies, and these lemon curd cookies and these soft pumpkin cookies.
Searching for more pineapple recipes? Pineapple Mint Mojito / Pineapple Salsa / Grilled Jerk Chicken Kebabs with Pineapple / Pineapple Coconut Dairy Free Baked Oatmeal
Ingredients & substitutions
- Butter-flavored shortening -This is one of my favorite dairy free butter substitutes. It mimics the taste and texture of butter, which is especially useful in recipes where you want that buttery flavor without using actual dairy. It helps give baked goods a rich, smooth texture similar to what butter would provide. Plus, it blends well with other ingredients, making it a handy option for all sorts of recipes.
- Crushed pineapple – 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.
- Maraschino cherries
Making changes to a recipe can result in recipe failure. Any substitutions listed below are simple changes that I believe will work in this recipe, but results are not guaranteed.
The following is a detailed overview of the recipe steps with added tips and tricks for recipe success. For a simplified and printable version, including ingredient amounts and more formal instructions, see the recipe card below.
How to make upside down pineapple cookies
Mix the dry ingredients. In a mixing bowl, combine the flour, baking powder, baking soda, and salt. Use a whisk to thoroughly mix them together, this helps to ensure that the baking powder and baking soda are evenly distributed throughout the flour. Once well combined, set the bowl aside for later.
Cream the shortening. In the bowl of an electric mixer, start by beating the shortening and brown sugar together until the mixture becomes light and fluffy. That should take about 2 minutes, then add in the egg, vanilla extract, and crushed pineapple. Continue mixing until everything is well combined and smooth.
Incorporate the flour mixture. Add the flour mixture in about 1/2 cup increments, mixing each addition until it’s fully incorporated. Make sure to scrape down the sides of the bowl as needed to ensure everything gets mixed in well.
Scoop and bake. Scoop the dough onto some parchment paper with a medium cookie scoop, making sure to leave about 1 1/2 inches between each cookie. Pop them in the oven and bake for 15 to 18 minutes, or until they’re golden and the tops look set.
Make the frosting. Mix the shortening, sugar, salt, and 2 tablespoons of pineapple juice with an electric mixer until smooth. If you need to, add more pineapple juice until you get the consistency you want.
Frost the cookies. Top each cookie with a generous amount of frosting and 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.
Ingredients
- 1/2 cup shortening
- 2 1/2 cups confectioners’ or glazing sugar
- Pinch of coarse salt
- 4 tablespoons pineapple juice
- 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
- Maraschino cherries
Instructions
For the cookies:
- Preheat oven to 350˚F and line a baking sheet with parchment paper.
- In a large bowl, whisk together flour, baking powder, baking soda and salt. Set aside.
- In a large bowl with an electric mixer, cream shortening and brown sugar at medium speed until light and fluffy, about 2 minutes.
- Add egg, vanilla and pineapple. Continue to beat until incorporated.
- Add flour mixture, about 1/2 cup at at time, until incorporated, scraping sides as needed.
- 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.
- Remove from oven and allow cookies to rest for about 5 minutes before transferring to cooling rack.
For the frosting:
- 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.
- Frost each cookie with a generous portion of frosting and top with a maraschino cherry.
