Place two scoops of vanilla ice cream into each glass.
Top each glass with half of the hot espresso, or 1/4 cup each.
Next, make the cocoa whipped cream. In a heavy mixing bowl, combine whipping cream and vanilla extract and whip until soft peaks form.
In another small bowl, combine confectioners sugar and cocoa. Gently stir the cocoa / sugar mixture into the cream and whip until well blended. Top the Afogato with the cocoa whipped cream and serve immediately.