Abstract: An outgoing email server inserts electronic advertisements in outgoing email messages. The server creates enhanced email messages in which the original plain email message text is framed with one or more electronic advertisements, as well as banners or footers related to the company or organization where the email author is employed. The system allows the assignment of one or more keywords to each electronic advertisement to facilitate the placing of electronic advertisements on a contextual basis. The preferred system searches the text of the outgoing email message for the one or more keywords assigned to the electronic advertisement. In another aspect, the system uses a database including email addresses for prospective recipients and assigns targeting words to those email addresses. If these targeting words match the keywords assigned to the advertisement, the advertisement will be placed. The system also allows electronic advertisements to be placed on a static or rotating basis.

Abstract: An outgoing email server inserts electronic advertisements into outgoing order confirmations and order cancellation notices generated by an online retail system. The server creates an enhanced email order notification in which the text of the email is framed with one or more electronic advertisements, as well as banners or footers related to the company or organization hosting the online retail system. The system searches for product identification codes, such as SKU numbers, for each product purchased by the customer at the online store in the case of an order confirmation notice, or for each product for which an order has been canceled in the case of an email order cancellation notice. In the case of order confirmations, the system statistically correlates the frequency that various products have been sold contemporaneously in the same shopping cart by past customers, and places advertisements in the outgoing order confirmation based on that statistical analysis.