<i>Information and Communications Technology (ICT) has made major advances in linking physical dimension through information to cognitive dimension as described by John Perry et al. (2004) in their model for Information Superiority. The information technology linkage between the physical and cognitive dimensions has created new ways of effect both for the red and blue force.</i><br><br> <i>The paper focuses on the information dimension and searches for better models to describe the structure of blue force information, especially from the Enterprise Architecture (EA) approach. Enterprise Architecture has been developed to better communicate the complex structures of military capabilities. Major EA frameworks (TOGAF, DODAF) recognise the layer of information between business and technology, but in practice, the focus turns more to the technology as has happened in several Command, Control, Communications, Computing, Information, Surveillance, and Reconnaissance (C4ISR) and Enterprise Resource Management (ERM) programmes. The paper develops a tool for architects to use in measuring the maturity of information management in the current military organisation and in defining the possible paths of evolution in information management available for the military.</i><br><br> <i>The outcome of this paper is a roadmap picturing the evolution of military information management. Enterprise Architects may use the roadmap in analysing and developing both C4ISR and ERM capabilities in military organisations. The primary research question for this paper is: What may cause so many failures in defining Enterprise Architecture at information management level and then in implementing C4ISR and ERM tools?</i><br><br> <i>The paper first defines six stages for management of unstructured information from various former studies and information architecture models (Cook, 1996). The basic stages of evolution of unstructured information are defined as print, file, page, social media content, semantic content, and intelligent content.<i><br><br> <i>These six stages and a generic military structure are processed through an evolutionary model derived from evolutionary theory for technical development described by Joel Mokyr (1998). The Mokyr model helps to recognise the paths of evolution, the forces that may influence the development and the ways that have been taken in achieving goals.</i><br><br> <i>The outcome is a roadmap that describes the evolution of past and possible future for military information management and explains different drivers and constraints on roads. The roadmap is aligned with other similar roadmap tools Enterprise Architects are using. The roadmap is further tested against experiences gained from several C4ISR and ERM focused military transformations. The overall research approach follows the hypothetico- deductive model (Brody, 1993) and the roadmap part applies the theory of evolution in sociotechnical systems (Bertalanffy, 1969).<i><br><br> <i>Military organisations have followed the general evolutionary path (print – file – page – social media content – semantic – intelligent content) in developing their management of unstructured information. The general path includes two definite leaps that require more effort: 1) from files to pages, and 2) from unstructured content to more structured content. There have also been more discrete shortcuts together with downgrades defined by cultural and doctrinal powers of the force.<i><br><br> <i>Meanwhile, it is possible to accelerate evolution by taking shortcuts. A consistent effort to change technology, processes, and people at the same time is needed when, for example, taking force from publish-pull pages to semantic information management. It might be easier to start with structured information and then, gradually, include unstructured information.</i><br><br> <i>Strong forces may also pull back already achieved development if the change has not been made to stick properly. Losing the thin trust for shared information management early in implementation may prevent individuals from sharing for a long time. Not providing the expected level of availability of the service for the knowledge base may lose the confidence of process owners.</i><br><br> <i>Since information is essential for cognitive level sense making, decision making, and learning, Enterprise Architects should include information maturity in their roadmaps of technical and business process development. The roadmap for military information management is to help analysis of the current situation and provide possible paths towards future stages aligned through business, information, and technical layers.<i><br><br> <i>The research in this paper only covers the approach of evolution. The systems and business strategy approached are studied in other papers. This article does not illustrate the integrated roadmap of business, information, and technology, which can be found in further papers by the writers. The research is based mainly on qualitative data in proving the roadmap. There is room for further assurance when the information sharing cultures of the military are enabling it.</i>