A postage printing system, comprising a computer (150), a data center (200), a control system (152,202) and a redemption center (500). The computer (150) is in operative communication with a printer (120) for printing a postal indicium on an envelope (20). The data center (200) is in operative communication with the computer, which in turn is located remotely from the data center. The data center includes a plurality of user accounts (204) and a plurality of advertiser accounts (206) where each of the plurality of advertiser accounts includes respective ad data including coupon data and restriction data. The control system is in operative communication with the data center (200) and the computer (150) and is for: (i) establishing a transaction session between a user of the computer corresponding to one of the plurality of user accounts and the data center; (ii) obtaining recipient address information from the user; and (iii) using the recipient address information and the restriction data from the plurality of advertiser accounts to identify coupon data available for printing on the envelope in conjunction with the postal indicium. The redemption center (500) is in operative communication with the data center (200) and coupon redeemers for reconciling payments corresponding to redeemed coupons.