The purpose of this research is to critically inquire into the appropriateness of the current human computer interaction (HCI) practices in Information and Communication Technologies and Development (ICTD) system design given the contextual constraints and challenges found in developing country contexts. Despite user participation in system design being a buzzword of HCI the form of this participation varies with the different disciplinary perspectives and paradigms and their different methods for engaging users and identifying users' needs. Moreover, a majority of these dominant HCI perspectives are not only rooted in the developed countries context they also mainly focus on organisational management information systems (MIS) and less on information systems (IS) that place emphasis on the socio-economic context of developing countries. Literature review reveal that limited studies focus on the differences brought about by the western influenced methodologies and principles when applied in different contexts and how they affect the user participation process as well as the outcome. Building on past research, this research argues that HCI for ICTD needs to develop new contextualised participatory methods and strategies that consider the broader and complex contexts of the ICTD users. However, shifting the focus to localised forms of HCI in ICTD system design requires a better appreciation of the challenges and constraints encountered when applying the traditional HCI methods and strategies. Based on this argument the research conceptually explores and reflects on the underlying contextual factors and mechanisms present in participatory ICTD system design and the presumed relationships among them. Drawing on this conceptual framework, the research conducts semi-structured interviews, focus group discussions and participant observations with three mobile money system design projects in Kenya that engaged the users during the design process to highlight how current HCI practices respond to the multifaceted nature of ICTD system design which present challenges that include social, technical, cultural and infrastructural issues. Findings from this qualitative study provide significant new insights that support the call for contextualised participatory methods and strategies. The findings suggest that there is tension between the underlying assumptions inherent in western HCI methods and strategies and the local context thus justifying the call for the appropriation of the design process. Drawing on the conceptual framework it was found that bias formed from factors such as power relations, diversity in interests for participation and cross-cultural differences moderate the design process and ultimately the participatory outcome.From the knowledge perspective, this research provides an in-depth understanding of the developing country contextual factors that mediate user participation process in ICTD system design. Furthermore, the research extends the knowledge with regards to participatory interventions in the development of IS in Africa. The research also presents a theoretical framework that makes explicit the contextual assumptions and constraints embedded in participatory ICTD system design interventions and how they shape the design process and the participatory outcome. Finally, the recommendations formulated from this research provide HCI designers and practitioners actionable knowledge in regards to reflecting on their current traditional HCI tools and techniques to ensure better localised design processes.