Gather your ingredients so that you have everything on the counter or table.
Prepare two tall glasses by drizzling caramel onto the sides of each. Add ice to each.
In a large container, stir together the cold (or room temperature) dark roast coffee, granulated sugar, and vanilla extract.
Add milk to the coffee mixture and stir to blend. Pour into prepared glasses. (Alternately, you may wait to add the milk until after filling glasses with the coffee. Add milk as desired and then stir to blend into the coffee for a "stained" macchiato appearance.)
Top with whipped cream and drizzle with more caramel.