Information technology (IT) projects regularly fail. IT projects fail rapidly, spectacularly and with monotonous regularity. IT and related information systems (IS) projects seem more prone than other technology-based interventions to prove to be enormously risky ventures for companies and government agencies to invest in. If this phenomenon is pronounced in so-called industrialised economies - the issues and problems around failure multiply when such projects are undertaken in transitional and developing economies. In all this failure the role of the IS practitioner appears invidious. On the one hand there are rapidly developing technologies and opportunities for change while on the other there are organisations often unable to express what change they desire or to articulate the difference between what they would like and what they feel able to cope with. It is little wonder that the IS practitioner—given the responsibility to manage the change process by analysis and design and other mediating strategies, can end up as the victim of technology failure, organisational inability to make up its mind and half-developed applications. In all this muddle the role of the action researcher (AR)—deeply involved with the processes and relationships within the research context is oddly empowered to deal with change while appearing even more vulnerable than his or her more managerialist or technologist colleagues. This chapter, by means of a reflective discourse representing my own learning, attempts to develop the theme of the vulnerability and power of the action research IS practitioner. Using current case study material drawn from working in transitional economies, the chapter indicates lessons learned in the value of the AR approach to analysis and design and the real benefits and powers which can arise from vulnerability such as autonomy and viability.