The concept of Maritime Security Operations was finally agreed upon in NATO. The framework now provides a basis to be able to legitimately perform security operations by using current and future maritime capabilities. Modern maritime operations require a comprehensive situational awareness picture in order to perform tasks in a more efficient and stinting manner. Regrettably, the strongest limitation is due to the limited available number of necessary assets (either maritime and/or air) to collect those data that must be managed by Humans (operators) before being distributed. However, because of the quantity of data to be exploited, decision making value can be diminished by an overlying flow of information, which might create wrong understanding (i.e., managing the whole instead of thinking and drawing on their own experience and then applying discernment to achieve “an” understanding on what is happening in the physical domain). Besides this problem, Coalition staff are more and more populated by heterogeneous operators with different profiles, which might inject “characteristic” errors, eventually spoiling the value of the local situational assessment. In the C4I World, we are observing a conceptual social revolution due to an unstoppable increase in the use of network technology to facilitate cooperation and information sharing within and amongst different social organizations, including civilian and non-military agencies of different countries. In these complex multi-domain settings, the label Network Enabled Capability (NEC) is used to describe the “assumed” increased value of a well-networked organization in order to provide decision superiority over opponents. However, in a complex networking environment, information sharing must be absolutely trustable, clear and able to provide correct meaningful information to users. This challenge is affected by political/legal constraints, technical issues related to system interoperability and by Human System Integration (HSI) errors that might cause wrong assumptions and diminish final quality. How much human perception may affect the cognitive process and, therefore, decision making, is a field we still must fully explore. Apparently, the operators' “geographical” attitude, operational service background and education might offer too subjective an evaluation during sensitive operations. Human understanding might be considered conditional and require a more holistic approach and new models to reduce judgment subjectivity.