Home-based work, also referred to as distance work, virtual work or Telework, is enabled by information and communication technologies, and has been in existence for over 35 years. Even with significant technological improvements, telework has not achieved widespread adoption. Of the many aspects of telework investigated, few studies have examined the effect of organisational features which can affect telework success. This research study examined the role of the organisation in telework adoption and explored the organisational factors that may positively or negatively influence telework diffusion. Telework success was approached as a multidimensional concept and the research draws from previous telework-related research to define a model based on a set of organisational factors, which were potentially able to affect telework adoption and diffusion. The model was tested by means of a dual case study of Information Systems (IS) personnel in two organisations. The comparative case study examined telework adoption in the organisations which were chosen as opposite polar types in order to examine the effect of the organisational factors in extreme opposites of telework maturity. An analysis of the case studies revealed that organisational factors are affected by the adoption process and values will change as telework practices mature. Additionally the relative contribution of each organisational factor was not equal and this changes over time so that the contribution of different factors will vary depending upon the maturity of telework practices in the organisation. Organisational factors that were not included in the original model but that should form part of future studies include national culture and the effect of industry type of the organization.