Not if he's upgrading to Digital from Analogue. The work order defaults to only 1 digital box, and the drop menu for equipment will allow a purchased terminal instead of a rental. Unless an agent actually adds on another outlet, adds the terminal, and adds the digital services fee all by accident, you'll only be charged one box.. and if the latter is the case, it wouldn't bill the account until the imaginary box is picked up, which would be never.
Also, for any purchased box being placed on an acount for the first time, please call 8772367208 for Cable Retail Fulfillment (Option 2 "To activate a Rogers product or service" after the language prompt). If you call regular Customer Care, you'll be transferred.