A system that alerts a sender of an email message as to the addressees of the email when the email is determined to be sensitive, such as when it includes a word such a “confidential”. The user can allow the message to be sent or go back to a mail create/edit operation where the message or list of addresses can be revised. Trigger words can be stored in a table or database. The system also detects sensitive words in attachments. The sensitive words detected and their locations can be shown in a pop-up message.