In this work, we consider the adoption and maintenance of information technologies into communities that we call 'hybrid workspaces' and the various temporal events that underpin moments of significant change. These events or 'points of vulnerability' can be identified and their impacts upon the community can be understood if due planning is undertaken. The paper describes the theoretical basis, the problems and the design of processes or instruments that are being developed to explore a particular workplace. In effect this work is research about and through technologies which are firmly located in social contexts. The organisation targeted by this research is an hierarchical and distributed community which features workers who are either permanent employees or volunteers, and whose communication technology needs are widely varied. The organisation can be regarded as a construction of several workspaces, some of which involve mobile work and others based in traditional office settings. Communication technologies involving print, telephony, two-way radio and a variety of computer mediated methods seek to "sew together" the organisation's operational and administrative functions. We recognize the interdependence of communication methods in hybrid workspaces such as these, and regard that this somewhat architectural view needs to be considered alongside a comprehensive analysis of the discursive practices that develop within. The study of this or any similar hybrid workspace is undertaken with the evaluation methods we are developing. These pay attention to an analysis of the technologies themselves within the social context and the inevitable changing social structures. In particular, we attend to the temporal location of work, and to the capacities of groups working with specific technologies. In the process of establishing these evaluation methods, is the selection and development of data collection methods which are either automated or otherwise mediated by communications technologies. The presents an opportunity to investigate the quality and secondary impacts of electronic and automated data collection and the ethical and technical considerations which arise. We are particularly interested in the responses of workers in the organisation to the impacts of the technologies which surround them. This includes the both the data collection which is routine within their work, and that which is introduced for the purposes of this study. Points of vulnerability are those significant instances and sequences of events in the implementation of technologies for workers. It is appropriate to identify and examine these moments. As we identify the impacts of the technologies in our own data collection and analysis, we create an overlapping hybrid community with its own events. An ability to recognize, or even predict these temporal events and their likely impacts leads us to better methods of understanding hybrid communities.