Pre-heat the oven to 350. Line a standard sized muffin tin with paper liners.
In a large bowl whisk together the dry cupcake ingredients: sugar, flour, cocoa, baking powder, baking soda, and salt.
Add the eggs, milk, vegetable oil, and vanilla and beat on medium for about 2 minutes.
Set the mixer aside and slowly pour and stir in the boiling water until it's completely combined and smooth.
Fill the prepared muffin tin cups to about ¾ full (I use a ¼ cup dry measuring cup to dip the batter) and bake for about 22 minutes.
A pick inserted into the center will come out clean. Let the cupcakes cool completely.
Using a small paring knife cut little circles about the size of a quarter out of the top of each cupcake.
In a small saucepan, melt the !/4 cup butter. Whisk in the ½ cup brown sugar. Bring it just to a low boil so the sugar dissolves and remove it from the heat. Scrape the mixture into a large bowl and let it cool a little.
When the mixture has cooled to the touch, add the vanilla and salt. Mix.
Using an electric mixer, add the flour ½ cup at a time. Then add the milk a tablespoon at a time until you've reached the desired consistency (thick like cookie dough!). Stir in the chocolate chips.
Refrigerate the cookie dough for about 10 minutes, just so you can roll it into cookie dough balls.
Pinch out enough dough to make about 1" balls, roll them, and then drop them into each cut-out cupcake.
To make the frosting, beat together the butter and brown sugar until fluffy. Add the vanilla and salt. Sift in the powdered sugar a cup at a time, beating in between each addition. Add the heavy cream a tablespoon at a time until you've reached your desired consistency. Add more powdered sugar to thicken if necessary.
Frost the cupcakes and top with more chocolate chips.
Recipe by Sugar Dish Me at https://www.sugardishme.com/chocolate-chip-cookie-dough-cupcakes/