IS adoption and evaluation remains a problematic area in theory and practice, and this is particularly the case for SMEs. The prior literature on IT/ IS adoption and evaluation has largely considered this area in terms of the factors influencing the decision to adopt. This paper takes the point of view that IT/ IS adoption may be better understood as a process, frequently cyclical, rather than a decision-type event. The research thus set out to explore the linkage between IT/ IS adoption and evaluation from a process perspective. An in-depth case study was conducted with a Thai medium-sized tourism enterprise which adopts e-business technologies to reach and serve its customers as well as to facilitate its back-end processes. Based on the contextualism theory (Pettigrew, 1987) and the appreciative system (Vickers, 1965), an interpretive framework is developed to help capture the dynamic changes occurred throughout the adoption and evaluation cycle. The case reinforces the prior literature that adoption and evaluation are framed by certain contexts. Overall, the research attempts to probe into the on-going process of IT/ IS adoption and evaluation occurring in SMEs and adds into the literature on IS evaluation in SMEs particularly with respect to the process aspect.