The great majority of the Knowledge Management (KM) and search tools on the market are server-based enterprise systems. As such, they are often designed top-down, centralised, inflexible and slow to respond to change. There has been numerous articles published on the role of IT and KM systems in organisations but there is a lack of research into KM tools for individuals and server-less KM tools/systems. By adopting a bottom-up approach, this research focusses on tools that assist the Individual Knowledge Worker (IKW) who, in today’s competitive knowledge-based society, has a constant need to capture, categorise and locate/distribute knowledge on multiple devices and with multiple parties. Furthermore, knowledge sharing between IKWs often extend across organisational boundaries. As a result, personal KM tools have very different characteristics to the enterprise KM tools mentioned above. At the group level, the impact of Peer-to-Peer (P2P) computing on Knowledge Management has been specifically identified as file sharing, distributed content networks, collaboration, and search. Potential applications for P2PKM systems include, among others, E-Learning in higher and distance education, real time collaborations and battle simulations in defence, collaborative product development, business process automation, and E-business payment systems. By including key findings from earlier work recently completed by the author and others on the landscape of enterprise KM systems, this paper presents a holistic view of the (commercial) KM technologies at three key levels of focusses – individual, group and organisational. This paper concludes with critical issues and the impact of PKM and P2PKM technologies on enterprise computing.