In 2 cup liquid measure or small bowl, combine milk, espresso powder, and vanilla. Stir thoroughly. Add chocolate syrup and stir again until most espresso powder is dissolved.
To soften ice cream, remove lid and liner (if any) of pint carton. Microwave at 50% (medium) power for 10-15 seconds, only until ice cream is slightly softened. Working quickly, scoop about half of the pint of softened ice cream into blender container. Pour on milk-espresso mixture. Cover and blend at high speed only until smooth. Serve immediately.
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