Disclosed is a computerized system and method for dynamically applying a rights management policy to a message by allowing an administrator to associate certain rights management policies with certain senders and recipients of messages, with groups of users possessing certain common criteria which define the users and groups of users, with certain attributes of the message, and with certain environmental attributes. In some embodiments, an administrator is allowed to automatically update a rights management protected message as it passes through a message transfer agent. The administrator may determine either on a regular interval or an ad-hoc basis that the message transfer agent scan the messages stored to determine whether or not the content has expired. If the content has indeed expired the administrator may take steps to have the expired content deleted entirely, refreshed with more current content, or replaced with a tombstone indicating that the original content has expired.