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Whisk heavy cream and vanilla syrup using a handheld milk frother. Whisk until you get stiffer peaks, which should take about a minute. Make sure to move the handheld milk frother up and down to get air into the heavy cream. Set aside.
Pour chocolate syrup and espresso into a cup. Stir together.
Add milk, then ice.
Top with whipped cream.Use a spoon to dollop the whipped cream on top of the drink.