This paper reports on research-driven design of social technologies. It describes an exploratory field study evaluating and re-conceiving blogging technologies – a mobile phone, a mobile blog, a Weblog and synchronization software – to support personal change, in this case quitting smoking. We briefly describe the design of the blogging technologies and summarise the outcomes of their extended use by four people trying to quit smoking in terms of technology usage, domestication and acceptance and, smoking cessation. We then document some notable features of failure, both of the technology and the quit attempts, describing how understanding the nuances and subtleties of failure highlights important design considerations. Finally, we present some methodological and design recommendations emerging from: a design workshop involving the participants in the field study; and a desktop design exercise.