Cookies and Cream Cupcakes

When I found a recipe on Pinterest for homemade Oreo cookies I was very excited. I love cookies and cream ice cream and always wanted to do a cupcake inspired by cookies and cream and mint. When I tried the recipe as seen here, I thought they were very good, but not very Oreo like and probably wouldn't work the way I needed them to work, so I modified it. The recipe in the link is a little cakey, the cookie is crisp on the outside but a little chewy. I didn't try the cream filling as I have an aversion to cooking with shortening. I have modified the cookie so it is crispy and not cakey at all, and the filling doesn't use shortening. So this recipe will be in two parts, the cookie and the cupcake. In the end I nixed the idea of the mint but I'm still very happy with how it all turned out. Before you freak out, know that these cookies are super easy to make, take no time to bake and can be made the day before if you want.

Cookies
1 1/4 cup of flour
2 cups of sugar
1/4 teaspoon salt
1/2 teaspoon baking soda
1/4 teaspoon baking powder
1/2 cup unsweetened cocoa powder
1 stick+ 2 tablespoons of butter at room temp
1 egg at room temp
Preheat oven to 375. Roll out small amounts of dough in your hand and flattened them with your thumb. Make 64 the size of a Nickel and place them on a parchment paper lined cookie sheet. Bake these in the middle of the oven for 7 minutes.
Make regular sized (Oreo size) cookies with remaining dough and bake in the center of your oven for 12 minutes.
Set aside to cool When your cookies are done set oven to 400



Chocolate Cupcakes
1 1/2 sticks room temp butter
3 eggs room temp
2 cups of sugar
2 cups flour
1 teaspoon baking soda
1/2 teaspoons salt
3/4 cup of high quality unsweetened cocoa
2 teaspoons of vanilla
1/2 cup of brewed coffee
1 cup of milk
Combine milk, coffee, and vanilla in a bowl or measuring cup. In a medium sized bowl, whisk together flour, salt, baking soda, and cocoa. Set aside.
Cream butter and sugar for 3 minutes. Add eggs one at a time mixing well between each. Add 1/3 of the dry mix and mix until combined. Add 1/3 of the wet and mix again. Continue to do this until everything is incorporated.
Fill muffin cups 3/4 of the way full. Drop your oven to 350 and immediately place cupcakes in the oven. Bake for 20 minutes, turning them for even baking after 12.
Set aside to cool.

Frosting and filling
2 sticks of butter softened
6 teaspoons of vanilla
6 teaspoons of milk
5 cups powdered sugar
1 cups smashed cookies

Whip butter until smooth, add 2 cups of sugar and mix well. Add vanilla and milk, and mix again. Add remaining sugar and mix until smooth.
Take out a few spatulas full and transfer it to a pastry bag with a writing tip on it. Put a little on half of the small cookies and use another one to sandwich them together. Set these aside. Take a small Ziploc bag and fill it with cookies. Push the air out and seal it. Now beat the tar out of it. You want these cookies to be dust so they don't clog your frosting tip. You may still get a clog here and there so have a tooth pick ready, but for the most part you want smooth sailing so pound the daylights out of those cookies. Once they are pulverized you can measure out a cup (or so) and put them in to you bowl of frosting, also add any left overs you have in the pastry bag from filling your cookies.
Now turn the mixer on high and blend well, scraping the sides at least once.




Now this frosting is sweet, and most of you know how I feel about super sweet. I need balance! I recommend you don't pile this frosting high, and I didn't give you a recipe that makes enough for that anyway. So fill a large pastry bag with the new cookie incorporated frosting and use a writing tip to make a small pile of frosting in the center of each cupcake. Top the cupcake with one of your homemade Oreos and press it down a bit.
Now if you would like to fill your remaining Oreo style cookies, I wrote the filling out in a way that makes it very easy to make just half the recipe.  ENJOY!