A method and system for preventing sending of messages to incorrect email recipients are provided. The method includes determining (120) the intended recipients of an email message prior to sending and comparing the intended recipients to defined recipient groups (126, 122). Potential errors in the intended recipients are identified and a prompt (125) is provided to amend the intended recipients. The prompt (125) provides a suggestion to replace, add or remove an intended recipient. The defined recipient groups include one or more of groups of recipients formed from an organization data structure (122), groups of recipients defined by a user, and groups of recipients (126) mined from one or more user's previous email correspondence.