In the bowl of a stand mixer, cream together the butter and sugar until smooth (about 4-5 minutes). Add the salt and cinnamon. Mix to combine.
Turn the mixer to medium and add the eggs one at a time until incorporated.
Set the mixer to low and slowly add the flour. The batter will be sticky.
Next, turn on your waffle iron 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 golden brown. Let the cookies cool and crisp up on a wire rack.
For the glaze, whisk together the powdered sugar, maple syrup, and salt until smooth. (If the mixture seems too thick, you can thin it with a little milk.) Dip the tops of each cookie into the glaze and return them to the cooling rack to set. Pack and store your waffle cookies in an air-tight container.