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1
Melt chocolate with 1 cup butter (2 sticks) in a saucepan over medium-high heat, stirring constantly.
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2
Let cool slightly.
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3
Put eggs, vanilla, and granulated sugar in the bowl of an electric mixer fitted with the paddle attachment.
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4
Mix on medium speed until pale, 4 to 5 minutes.
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5
Mix in chocolate mixture, salt, cinnamon, 1/2 cup cocoa powder, and the flour.
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6
Heat a waffle iron until hot.
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7
Lightly coat grids with cooking spray.
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8
Spoon about 1 tablespoon batter onto center of each waffle-iron square to make 1 1/2-inch rounds.
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9
Close cover; cook until set, about 1 1/2 minutes.
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10
Transfer to a wire rack, bottom sides up.
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11
Let cool completely.
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12
Repeat with remaining batter, coating grids with cooking spray after each batch.
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13
Melt remaining 2 tablespoons butter in a small saucepan over low heat.
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14
Add confectioners sugar and remaining 2 tablespoons cocoa powder; stir until smooth.
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15
Stir in milk.
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16
Gently dip one surface of each cookie in icing so that just the waffle lines (not gaps) are coated.
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17
Repeat with remaining cookies and icing.
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18
Transfer to wire racks; let stand until set, about 10 minutes.
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19
Dust iced surfaces of cookies with confectioners sugar.
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20
Cookies can be stored in single layers in airtight containers at room temperature up to 2 days.
