If you’re using black sugar, rim a chilled martini glass by lightly moistening the rim and dipping it in the sugar to create a “widow’s web” effect.
Fill a cocktail shaker with ice. Add the vodka, coffee liqueur, cooled espresso, and vanilla syrup.
Shake vigorously for about 15 seconds, until well chilled and slightly frothy.
Strain into the prepared martini glass.
Garnish with a few espresso beans or a twisted piece of black licorice to complete the “widow” effect.