Add ¼ cup of caramel syrup and 1 tablespoon of granulated sugar into the bottom of each glass.
Add about ¼ cup of coffee to the glass and then use a spoon to swirl the caramel, sugar, and coffee together to help the sugars dissolve.
Carefully add your ice to the cup. Some liquid may splash out of the cup.
Add ¼ cup of milk to each cup.
Use any remaining coffee to fill the glasses up to the top, stopping about ¼ of an inch from the rim so it doesn't overfill.
Stir to combine.
Top with whipped cream and drizzle some caramel syrup on top for garnish.