A method, a computer program product, and a computer system cognitively distribute email attachments to recipients. The method includes receiving an email composition for an email to be transmitted to a plurality of recipients, the email composition including at least one attachment. The method includes determining recipient information indicative of respective characteristics of the recipients. The method includes determining a context of a select one of the at least one attachment. The method includes, for each recipient, determining a score indicative of an appropriateness of the selected attachment being distributed to the recipient based on the recipient information of the recipient and the context of the selected attachment. The method includes, as a result of the score for a select one of the recipients satisfying a scoring threshold, distributing the attachment to the selected recipient via the email.