Chocolate Chip Cinnamon Roll Cookies with Chocolate Icing

These cookies made me realize how awful I am at drizzling icing on things.  I should have realized this when I made those salted caramel brownies with a pretzel crust, and it looked like a three year old  decided to make an art project out of the topping.  But I thought that maybe I just hadn’t found the right method for drizzling.


Also, that one had its own difficulties with the chocolate and caramel drizzle being piping hot from just being melted.  And then the caramel kept hardening as I tried to spread it over the brownies.  I had other things on which to blame my awful drizzle job.

But I can’t hide from the truth anymore.  This icing was not piping hot.  It was the right consistency, and I followed the exact instructions in the recipe.  Still, I ended up with  more chocolate icing on my counter than the cookies.

At least it tasted good.  REALLY GOOD.  The icing tastes like chocolate milk, guys, and it took everything in me not to drag my finger through the leftovers and eat it all.  I’m not sure I’ll have that willpower the next time I make these!


  While these cookies have a lot of steps, they really are pretty easy to make.  I thought the rolling would be difficult, but using plastic wrap makes all the difference.  Definitely add these to your cookie rotation!

Chocolate Chip Cinnamon Roll Cookies with Chocolate Icing


For the cookies:

1 cup butter, softened

1/2 cup brown sugar

1/2 cup sugar

2 eggs

1 tsp vanilla

2 tsp cinnamon

3 cups flour

2 tsp baking powder

1 tsp salt

1/2 cup semi-sweet mini chocolate chips

For the filling:

1/4 cup butter, very soft

1/4 cup, plus two tbsp packed brown sugar

1 tbsp cocoa powder

2 tsp cinnamon

1 to 2 tbsp mini chocolate chips

For the icing:

2 cups confectioners’ sugar

2 tbsp melted butter

2 tbsp cocoa powder

2 tsp vanilla

2-4 tbsp milk


For the cookies:

Mix the flour, baking powder, cinnamon and salt in a medium bowl and set aside.

In  a large bowl cream together the butter and sugars.  Add the eggs one at a time, mixing.  Add the vanilla and mix until combined.  Mix in the dry ingredients in two batches, letting the batter form before adding the next batch.

Gather the dough into a ball in the center of the bowl and cover with plastic wrap.  Let chill for 30 minutes in the freezer, or at least an hour in the refrigerator.

For the filling:

Mix together the the dry ingredients, except the chocolate chips, in a small bowl.  Leave the softened butter – you’ll use that in a minute.

Take out your chilled dough and divide it into two equal halves.  Take the one half and put it on a large piece of plastic wrap.  With a rolling pin, roll the dough out into a large rectangle, about 1/2 an inch thick.

Take half the softened butter and spread it on the dough.  Sprinkle half of the cinnamon-cocoa-sugar mix over the butter and then sprinkle a few chocolate chips to finish.  Using the plastic wrap to help you, tightly roll the dough like a cinnamon roll.  Wrap in plastic wrap and place in the freezer for 30 minutes.

Repeat with the other half of the dough.

For the actual baking:

Preheat oven to 350 degrees.

Once it’s chilled slice the dough just like you’d do for slice-and-bae cookies from the grocery store.  You should get about 20-24 cookies from each roll.  Place the cookies on a prepared baking sheet, about one to two inches apart.

Bake for 10-12 minutes.

For the icing:

Make sure the cookies are fully cooled before icing.  In a bowl mix together all the ingredients.  Add more or less milk depending on your desired consistency.  You want this a little runny so that you can drizzle the cookies, but not too runny.

Using your whisk, drizzle the icing on the cookies.  I found the best way to do this was using a cooling rack with a sheet of plastic wrap set underneath to catch the dripping chocolate.

Let cookies set before stacking or storing.


Source:  Bakingdom


8 thoughts on “Chocolate Chip Cinnamon Roll Cookies with Chocolate Icing

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