A user is writing an email or other message. The message is inspected for a predetermined word and for at least one of: a predetermined phrase or a template match. A score is generated if the predetermined phrase or the template match is detected. A suggestion is provided to a user that the message may need an attachment if the predetermined word is detected or if the score is greater than a predetermined score. The inspection may begin when the user begins creating the message, indicates that the message should be sent, or at some point in between. The user may provide feedback that the suggestion is accepted or that the suggestion is rejected.