In a medium bowl, whisk together the flour and cocoa powder. Set aside.
In the bowl of a stand mixer, cream together the butter, sugar, and salt until smooth (about 4 or 5 minutes). Mix to combine.
Turn the mixer to medium and add the eggs one at a time until incorporated. Then mix in the vanilla and red food coloring. Finally, set the mixer on low speed and slowly add the flour. The batter will be sticky.
Next, turn on your waffle iron, lightly spray with PAM cooking spray, and set the temperature to medium-high (400 degrees F). Add about a tablespoon of dough to each section of the waffle iron. "Bake" for 2-4 minutes or until the cookies are golden brown. Let the cookies cool and crisp up on a wire rack.
For the glaze, beat together the cream cheese and powdered sugar and salt until smooth. Slowly begin to incorporate the milk until you achieve the desired consistency. You may not need all of the milk.
Dip the tops of each cookie into the glaze and return them to the cooling rack.
Decorate with sprinkles and serve with whipped cream.