The paper focuses on information dimension in the structure of Information and Communication Technology architecture and searches for better models to describe the structure of blue force information, especially from Enterprise Architecture (EA) approach. Enterprise Architecture has been developed better to communicate the complex structures of military capabilities. Major EA frameworks (TOGAF, DODAF, NAF) recognize the layer of information between business and technology. Nevertheless, in practice, the focus tends to turn more to the technology as has happened in several Command, Control, Communications, Computing, Information, Surveillance, and Reconnaissance (C4ISR) or Enterprise Resource Management (ERM) programs. The paper develops a tool for architects to use in measuring the maturity of information management in the current military organization and in defining the possible paths of evolution in information management available for military. The outcome is a roadmap that describes the evolution of past and probable future for military information management and explains different drivers and constraints on roads. The roadmap is tested against experiences gained from several C4ISR, and ERM focused military transformations. The overall research approach is following the hypothetico-deductive model, and the roadmap part is applying the theory of evolution in sociotechnical systems. 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 the analysing of the current situation and provide possible paths towards future stages aligned through business, information, and technical layers.