A system for identifying attributes associated with content of an e-mail message and alerting a user includes a client device programmed to allow a user to create an e-mail message including at least one recipient and a message content, a server programmed to check an attribute of the e-mail message, and to send the e-mail message, and one or more information stores in communication with the server, the information stores including information about the e-mail message. The server is programmed to query the information stores to obtain information about the e-mail message as the message is being composed by the user, and the server sends a mail tip to the client regarding the e-mail message. The client is programmed to provide the mail tip to the user, the mail tip being formatted and positioned by the client so that it is integrated within a header section of the e-mail message.