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In a small saucepan, add unsweetened chocolate and butter-melt over medium heat, stirring constantly. Remove from the stove and let cool slightly. In a large mixing bowl, add eggs, vanilla and granulated sugar-beat on medium speed with the paddle attachment until very pale -about 5 minutes. Add in chocolate mixture, salt, cinnamon, 1/2 cup cocoa and the flour. Preheat a waffle iron until hot. Lightly coat grids with cooking spray. using a tablespoon cookie scoop, portion out the batter between the center of each waffle-iron square. Pull down the cover and cook until set, about 1 1/2 minutes. Use a fork to help you coax the cookie off and move them to a wire rack to cool completely. Repeat with remaining batter.
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To make the glaze, In a small saucepan, melt 2 tablespoons butter. Stir in powder sugar and 2 tablespoons cocoa powder. Sitr in milk until smooth-remove from the heat. Gently dip 1 side of each cookie in the glze so that just the waffle lines are coated. Transfer to wire racks and let sit until the glaze has set-at least 10 minutes. Dust cookies with extra powder sugar before serving.
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