Brew a concentrated batch of coffee: make 1 1/2 cups (12 fl oz) using your preferred method, using roughly twice the usual coffee grounds so the flavor stays bold after ice is added. Aim for a 5-minute brew time for drip or press methods.
While the coffee brews, stir together the simple syrup and vanilla in a small bowl so the vanilla can bloom; if you don’t have simple syrup ready, dissolve 2 tbsp sugar in 2 tbsp hot water and cool briefly.
Fill two tall glasses with the ice. As soon as the coffee is ready, pour it over the ice to rapidly chill and slightly dilute the concentrate — this prevents a cloudy drink and cools the coffee fast.
Divide the milk between the glasses, then add half of the simple syrup–vanilla mix to each. For a creamier texture, use whole milk or substitute half-and-half for up to half the milk amount.
Stir each glass vigorously with a long spoon, or transfer the contents to a tight-lidded jar and shake for 10–15 seconds to emulsify and create a light foam on top.
Taste and adjust sweetness by adding a little more simple syrup if needed. Finish with a tiny pinch of ground cinnamon over the foam, then serve immediately.