The missing attachment problem: a missing attachment generates a wave of emails from the recipients notifying the sender of the error. We present an attachment prediction system to reduce the volume of missing attachment mail. Our classifier could prompt an alert when an outgoing email is missing an attachment. Additionally, the system could activate an attachment recommendation system, whereby suggested documents are offered once the system determines the user is likely to include an attachment, effectively reminding the user to include the attachment. We present promising initial results and discuss implications of our work.