Pineapple Upside Down Cookies

Posted by L.J. York on

I love a good dessert. Not just any bag cookie or snack cake will do. For the Holidays I always bake treats for numerous family members and friends. Last year I wanted to break out of the normal cookie “routine” and find something new to bake. I’m extremely picky so it took a while, but I finally came upon some pineapple upside down cookies. Fell in dessert love and had to give it a try. I mean, who doesn’t love cake turned into cookie form?

Just imagine... warm sugar cookie with dripping brown sugar, pineapple, and a cherry to top it off. Oh baby! You want, no, you need this in your life. Plus, there is fruit on top, so it’s technically healthy, right? Well that’s what I’m telling myself!

So, I found the recipe here. You can check it out to find the  original recipe, how-to video, and a printable version. I’m not totally sure who the original creator is, but who ever they are I applaud them! Wipe the drool off and let's get baking!

There are some simple ingredients. While it is a bit labor intensive totally worth it! Keep in mind, the sugar cookie part is a bit more dense then your average sugar cookie to hold up under the toppings.

  • 1 cup butter room temperature
  • 1 1/2 cups granulated sugar
  • 2 eggs
  • 2 tsp. vanilla extract 
  • 1/2 cup sour cream
  • 3 cups all purpose flour
  • 1 tsp. baking powder
  • 1 tsp. corn starch 
  • 1/2 tsp. salt
  • canned pineapple slices
  • maraschino cherries
  • 1/2 cup butter melted
  • 1 cup light brown sugar packed

This took me about an hour to get in the oven. I ran into a huge problem when I realized I didn’t have a mini round cake pan. Which is a bit bigger than a cupcake pan. While one might just go buy the pans, I of course stuffed it in my cupcake pan! Here are the steps I used to cook them in a cupcake pan if you don’t have the other.

  • Preheat oven to 350 degrees. Set aside cupcake pan.
  • In a mixing bowl, add butter and sugar, mix until light and fluffy.
  • Add in the eggs, vanilla extract, sour cream. Mix until combined.
  • Add in the flour, baking powder, cornstarch, and salt. Mix until the cookie dough just comes together. Set aside.
  • In a separate bowl, stir together the melted butter and brown sugar until combined.

(here comes the fun part)

  • Add 1-2 teaspoons of the brown sugar mix into the bottom of each muffin hole (whatever, you know what I’m talking about). Spread it evenly. 
  • Trim pineapple slices so they fit in bottom of rounds. I cut a section out and trimmed the inside of each ring (equals tasties for you!).
  • Add the pineapple slice on top of the brown sugar and the cherry in the center of the pineapple.
  • Add 1-2 teaspoons of cookie dough to the top. I used a butter knife to smooth it out.
  • Place into the oven and bake for 25 minutes or until the edges are golden brown and the brown sugar is bubbling up the sides (or in my case, bubbles over sides). 
  • Let cool for 10 minutes and then turn over onto a parchment paper covered surface. Trust me, you don’t want to skip this step! If you do there will be consequences.
  • Lightly tap the bottom of the pan to make cookies release if necessary.

My suggestion would be to use a cookie sheet under your pan while cooking to catch any sugar that bubbles over. I made a mess lol! Personally I preferred them the next day, but who can resist! They only last a few days so eat up or share! 

If you try these I hope you enjoy! If you have a favorite recipe and want to share, I’d love it! Stay tuned for our next post about why we started AMUL.

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