Make the chocolate syrup (makes about 1 cup, keeps 2–3 weeks in fridge):
In a small saucepan, whisk together the cocoa powder, sugar, salt, and water until no lumps remain. It will look gritty at first – that's fine.
Place over medium heat and bring to a gentle simmer, whisking occasionally. You'll see it start to thicken and turn glossy. When it begins to bubble around the edges and coats the back of a spoon, it's ready (about 2–3 minutes). Do not let it boil hard.
Remove from heat and stir in the vanilla. Let cool for a few minutes, then pour into a clean jar. It will thicken more as it cools.
Assemble the mocha iced coffee:
Fill a tall glass with ice cubes. Pour the milk over the ice.
Add 1–2 tablespoons of the cooled chocolate syrup directly into the milk. Stir a little so some syrup swirls into the milk – this creates the pretty streaks.
Pour the strong coffee or cold brew concentrate over the back of a spoon to layer it on top. If you want it fully mixed, stir well. I like to leave the first inch mostly coffee for that dramatic gradient.
Taste and add more syrup if desired. Top with whipped cream and a sprinkle of cocoa if you like. Serve immediately.