Methods and systems enable evaluating a message prior to transmission to one or more addressees. In an embodiment, a message element evaluator applies rules to message field elements which may include message addressee and content elements before the message is transmitted. When a message evaluation rule is violated, an alert may be presented to the user. A message evaluation rule may allow the sender to confirm sending of the message, initiate editing of the message, or cancel the message. A message evaluation rule may also prohibit the message from being sent until the message is modified to conform to the message evaluation rule. The methods and systems may be applied to a variety of message types including electronic mail, simple message system, multimedia message system, and instant message system messages.