I use affiliate links in some of my blog posts. This means that I could make a commission if you click on a link and purchase something. Read my full disclosure here.
I am not a big fan of regular sugar cookies. In fact, they’re probably my least favorite type of cookie. Shocking, I know.
Unless they happen to be chocolate. I love chocolate sugar cookies. There is just something about the crunch of sugar with the light hint of cocoa that makes these so delightful and irresistible to me.
So when I worked on this recipe initially, I was going for a fluffy, sugar-crusted chocolate cookie. And it really seemed like the perfect recipe. Until I pulled them out of the oven. They came out completely flat (kind of like my first batch of chocolate cupcakes in this Coffee-Frosted Chocolate Cupcake recipe). They were not at all the sugar-crusted beauties I envisioned.
It was disappointing, to say the least.
I was majorly bummed. I contemplated trashing them. It really seemed like a failure and a lost cause.
And then I tasted one. Mmm mmmm! The flavor was fantastic and the crispness was simply delightful! So I figured I’d salvage them into some chocolate sandwich cookies (or copycat Oreos). The Hubs is an Oreo addict. So mush so that I usually have to hide them from him or he’ll eat the entire package in less than a day! And when I had him taste test these, he gave two thumbs up to the new twist.
So the question became, what do I do for a filling? I have an excellent, ooey gooey marshmallow filling for my family favorite Whoopie Pies. But that would be much too soft for a chocolate sandwich cookie filling. But I considered adapting it to be a little stiffer so that it would hold up to the crisp chocolate sugar cookies.
So I mixed together this filling with a little trial and error. It turned out great. And let me tell you, these cookies are to die for. I don’t love Oreos, but I could demolish a plate of these without a problem! The Hubs could not stop eating them. I think I may be able to replace the store bought ones for good!! In fact, this filling would be delish between a couple of my Brown Butter Pecan Cookies.
Dip one of these chocolate sandwich cookies in a glass of milk and taste the chocolaty goodness! You might want to find a good hiding place for these because chances are, everyone is going to eat up these chocolate morsels! I know I’ll be finding a place to hide these from the Hubs. If you want more chocolate, head on over to my Chocolate Stout Bundt Cake recipe. It’s a chocolate lovers dream!
My only note of caution is when filling the cookies. Make sure you place the cookie on a flat surface when spreading on the filling. Otherwise you’ll end up breaking some of them because the filling is thick and needs a little pressure to spread it out. The cookies are fairly firm, but will break if you just hold them. I learned this by experience!
What’s your favorite way to eat a sandwich cookie? With a glass of milk or a cup of coffee? Do you like it best with a traditional filling or with ice cream?
Chocolate Sandwich Cookies
For the Cookies
- 14 Tbsp unsalted butter room temp
- 1 ¾ cup light brown sugar lightly packed
- 1 Tbsp vanilla extract
- ½ tsp salt
- 1 large whole egg and egg yolk
- 1 ½ ounces dark melting chocolate wafers (roughly 1/3 cup)
- 1 ½ cup flour
- ⅔ cup cocoa powder
- ½ tsp baking soda
- ¼ tsp baking powder
- ½ cup granulated sugar for rolling the dough balls in
For the Filling
- 2 Tbsp marshmallow fluff
- ½ cup shortening
- 1 tsp vanilla extract
- pinch of salt
- 2 ½ cups powdered sugar sifted
- 2 Tbsp cold water (ice cold!)
To Make the Cookies
- In a small microwavable bowl, heat chocolate wafers for 30 seconds. Stir until completely melted and smooth. You can reheat for 10 second intervals until melted.
- In a stand mixer, cream together butter, brown sugar, salt, vanilla, egg and egg yolk until just combined.
- Beat in melted chocolate to butter mixture.
- In a separate bowl sift flour, cocoa, baking soda, and baking powder. Gradually beat this mix into the wet ingredients, scraping down sides until combined.
- Cover and chill dough in the refrigerator for at least 30 minutes.
- After at least 30 minutes, take cookie dough out and use immediately. Using a small cookie scoop or teaspoon, roll small dough balls and roll each one in granulated sugar.
- Place dough balls on a cookie sheet lightly greased or lined with parchment paper. Use the bottom of a flat, floured glass to lightly flatten each cookie.
- Bake for 10-12 minutes. Bake until flat and spread out. Edges should be slightly firm to the touch.
- Let cool for 5 minutes before transferring to cooling rack.
To Make the Filling
- Beat together the marshmallow, shortening, vanilla, and salt. Add in powdered sugar until incorporated into a dry crumble.
- Add in 1 tablespoon of water at a time, looking for a smooth, creamy mixture.
To Sandwich Cookies
- Once cookies are completely cooled they should be somewhat firm to the touch. Place a cookie on a flat surface. Gently spread about a tablespoon (or more!) of filling and top with another cookie.
- Store at room temperature in an airtight container for about a week.