As the criticality of e-mail for electronic business activity increases, adhoc e-mail implementation, prolonged management neglect and user abuse of e-mail systems have generated negative effects. However, management’s ability to rectify problems with e-mail systems is hindered by our understanding of its organisational use. Research on e-mail systems is often dated and based on quantitative methodologies that cannot explain the interaction between various controls in organisational settings. Updating our understanding of the organisational aspects of e-mail systems utilizing qualitative methods is necessary. This chapter presents a multiple case study investigation of e-mail system monitoring and control. The study examines the interaction between key elements of e-mail control identified by previous researchers and considers the role of such controls at various implementation phases. The findings reveal eight major elements to be particularly important in monitoring and controlling e-mail systems within the organisations studied. These are: (1) form a cross-functional e-mail system management team; (2) implement and regularly update e-mail management software; (3) formulate a detailed and legally sound e-mail policy; (4) engage in structured e-mail system training; (5) create and maintain ongoing awareness of e-mail policy; (6) engage in a process of hybrid feedback and control-based e-mail monitoring; (7) firmly enforce discipline in accordance with the e-mail policy; and (8) conduct regular reviews and updates of the e-mail management programme.