Brew 2 ounces of espresso or strong coffee. Rest it so it completely cools before mixing.
In a 12-ounce glass, mix the Jack Daniel’s Bonded and maple syrup with the cooled coffee. Add ice and a straw and give it a swirl.
In a separate glass, combine the Vespertino and heavy whipping cream and froth for 15-20 seconds, until the mixture thickens but doesn’t firm up. Pour the cold foam over the coffee mixture.
Garnish with a sprinkle of cinnamon.