For the Cookies:

1. Spray and heat up your waffle iron to medium while you are making the cookie batter.  (The temperature settings run from 1-5 on my waffle maker.  I set it at 3.)
2. Melt the butter in a 3 quart sauce pan.  Only heat long enough to just melt it.  You don’t want it to become super hot.
3. Once the butter is melted, remove the pan from the heat and mix in the cocoa.
4. Add the sugar and vanilla.  Stir thoroughly to bring everything together.  This will also help cool the mixture in the pan.
5. Test the mixture in the pan by touching it.  It’s okay if it’s warm.  You just don’t want it to be so hot it cooks the eggs.
6. Beat the eggs into the chocolate mixture.   Continue stirring until everything is combined.
7. Finally, stir in the flour.  Continue stirring until all the ingredients come together evenly.  Your waffle cookies batter will be thick and similar to the consistency of fudge brownies.
8. Use a spoon ( I just use a spoon from the silverware drawer.)  to drop the waffle cookie batter onto your hot waffle iron.  I can do 4 at a time in mine.  Adjust according to your own waffle maker.
9. Bake the Chocolate Waffle Cookies in the waffle maker for 1 minute.  Remove to a cooling rack.
10. Repeat the process until all the chocolate waffle cookie batter has been baked.

For the Fudge Frosting:

1. Melt the butter in a 3 quart saucepan.
2. Remove from heat.
3. Add the cocoa powder to melted butter and stir to form a thick paste.
4. You can transfer the cocoa/butter mixture to the bowl of your stand mixer if you don’t own a hand mixer.  I actually use my hand mixer and do it all in the same 3 quart sauce pan.  You will want a mixer though as the powdered sugar can get pretty lumpy if you try and mix it by hand.
5. Add milk, vanilla and powdered sugar. (Start with only 2/3 cup milk. Mix it all together and then decide if you need more . If you think you do, add a Tablespoon at a time until you reach the desired consistency.)
6. Beat with your mixer until all ingredients are thoroughly combined.
7. The frosting will be thick.  But you do want it spreadable.  You can add more powdered sugar or extra milk to get your desired consistency, keeping in mind that this frosting will get firmer as it sits in the fridge.  Resist the urge to add more than you need.  Start with a teaspoon at a time of extra milk to thin it or a Tablespoon at a time of powdered sugar.  A little will go a long way.  The pictures above are a good gauge of the consistency we like.
8. Use the frosting to frost your Chocolate Waffle Cookies.