An interactive personal surveillance and security (IPSS) system for users carrying wireless communication devices. The system utilizes portable communication devices that are also capable of capturing and/or sending surveillance information. The system allows users carrying these devices to automatically capture surveillance information, have the information sent to one or more automated and remotely located surveillance (RLS) systems, and establish interactivity for the verification of determining secure or dangerous environments, encounters, logging events, or other encounters or observations. The RLS systems receive information from user communication devices and can follow user-definable parameters that establish the level or type of interactivity and determining when alarms or messages to third parties are needed. An IPSS system is user-definable and may become tailored and may respond to one or more users differently, based on each user's set-up and changes to the system. The interactive personal surveillance system may also react differently based on users' location, the users' potential safety or risk, when the users react differently to an event, others around them, etc.