This chapter investigates the possibilities of computer systems and technologies, currently being developed within the field of computer vision and image processing, to support operators in surveillance centres to monitor and remain aware of events and activities in the remote domain. Despite the long-standing interest in the social and cognitive sciences with awareness and monitoring, the design of these systems and technologies seems to present novel challenges for supporting monitoring tasks in complex and dynamic work settings. This may suggest why the deployment of advanced surveillance systems has remained somewhat limited and why it is unclear how to take advantage of advanced automation and processing functionality without making surveillance work expensive and difficult for the staff to manage. We wish to show how detailed understandings of everyday monitoring practice and organisational conduct may inform the design and development of image processing systems to enhance the awareness and monitoring of complex physical and behavioural environments. The setting in question is operations rooms of complex interconnecting stations on London Underground and other rapid urban transport systems in Europe. The chapter will begin by exploring the tacit knowledge and practices on which operators in these operations rooms rely in identifying and managing events and then reflect on the implications of these observations for the design of technical systems to support surveillance.