Where the role of software-intensive systems has shifted from the traditional one of fulfilling isolated computational tasks, larger collaborative societies with interaction as primary resource, is gradually taking its place. This can be observed in anything from logistics to rescue operations and resource management, numerous services with key-roles in the modern infrastructure. In the light of this new collaborative order, it is imperative that the tools (compilers, debuggers, profilers) and methods (requirements, design, implementation, testing) that supported traditional software engineering values also adjust and extend towards those nurtured by the online instrumentation of software intensive systems. That is, to adjust and to help to avoid situations where limitations in technology and methodology would prevent us from ascertaining the well-being and security of systems that assists our very lives. Coupled with most perspectives on software development and maintenance is one well established member of, and complement to, the development process. Debugging; or the art of discovering, localising, and correcting undesirable behaviours in software-intensive systems, the need for which tend to far outlive development in itself. Debugging is currently performed based on a premise of the developer operating from a god-like perspective. A perspective that implies access and knowledge regarding source code, along with minute control over execution properties. However, the quality as well as accessibility of such information steadily decline with time as requirements, implementation, hardware components and their associated developers, all alike fall behind their continuously evolving surroundings. In this thesis, it is argued that the current practice of software debugging is insufficient, and as precursory action, introduce a technical platform suitable for experimenting with future methods regarding online debugging, maintenance and analysis. An initial implementation of this platform will then be used for experimenting with a simple method that is targeting online observation of software behaviour.