Systems and methods allowing an instant messaging user to exchange messages with an e-mail user. To the instant messaging user, the experience is a seamless exchange of instant messages; to the e-mail user, the experience is a seamless exchange of e-mail messages. Conversion of an instant message to an e-mail message includes insertion of a token into the e-mail message, and conversion of an e-mail message to an instant message includes validating a token extracted from the e-mail message.