The present invention provides a method for automatically determining, and accordingly prompting an email user as to whether an attachment is to accompany an email message prior to transmission of the message. In one embodiment, the present invention provides a method, which can prompt an email user as to whether an attachment is to accompany an email addressed to certain individuals, groups, or organizations, prior to transmission of the message. In one embodiment, a database of certain addressees to whom attachments are frequently transmitted is consulted. In one embodiment, the present invention provides a method, which automatically prompts users based on the content of an email message as to whether an attachment is desired prior to transmission. In one embodiment, a database of certain keywords appearing in message text frequently correlated with attachment inclusion is consulted. In one embodiment, the databases are automatically updated by a self-learning modality.