Worldwide, governments and representatives of the community sector believe that the adoption of ICT by community-sector organisations is important because it contributes to the achievement of mission, strategic and business objectives, and benefits the communities those organisations serve. However, despite the fact that many organisations have developed innovative ICT applications, most experience problems in taking up ICT (Burt & Taylor 1999, Surman 2001, DCITA 2005b). This thesis explores the conditions for success and barriers to the take-up and effective use of information and communications technology (ICT), specifically websites and online services, by community-based non-profit organisations, using a study of seventeen organisations based in rural and regional Victoria in Australia, and Tuscany in Italy. In particular, it examines the structural barriers and the inter-organisational relationships that act to facilitate the take-up, or otherwise, of technology by community sector non-profit organisations. The study adopts a grounded theory approach, based on a two-stage data analysis: using the LIAISE framework for the take-up of ICT (Schauder et al. 2005), to identify the factors or conditions that contribute to the development of effective, sustainable websites; and social network analysis to explore the extent to which organisational networks enable the achievement of those conditions. The broad aims of this approach are to enable the evaluation of the existing LIAISE framework and to develop it as a more dynamic systems model capable of serving as a guide to policy and action. The study finds that although the LIAISE framework provides a good taxonomy of the factors important to the take-up of ICT by community-based non-profit organisations, it has weaknesses in that it does not explicitly identify user literacy as a factor, nor does it sufficiently emphasise the importance of an organisation’s external relationships, which provide an essential means of accessing required information and resources such as technical skills, and of enhancing core internal skills such as the ability to develop strategic plans. A new model is proposed to address these weaknesses: ALLIANCE (Applications; Literacy; user Literacy; Infrastructure; Access; Networks; Computing support; and Evaluation).