How to Make It
In a medium saucepan, combine the milk with 1 cup of the sugar and stir over moderate heat until the sugar dissolves. Pour the milk into a large bowl and let cool to room temperature. Add the vanilla and refrigerate until chilled. Freeze the ice milk in an ice cream maker according to the manufacturer's instructions.
In a medium saucepan, boil the espresso with the remaining 1 cup of sugar over moderately high heat until reduced to about 1 1/2 cups, about 10 minutes. Pour the syrup into a bowl and let cool to room temperature.
Scoop the ice milk into Champagne flutes and drizzle with espresso syrup. Garnish each serving with a dollop of whipped cream and a pinch of cinnamon