Network management software began to evolve in the 70's when network operating systems and the ARPANET raised. Before the invention of graphical user interfaces by Xerox, command line interface (CLI) driven software ruled the world. In terms of usability, CLI were and are efficient and error tolerant. After graphical interfaces, a new generation of security tools emerged and were adopted by young system administrators but, despite technological efforts that have been implemented so that computing infrastructure managers can control security features (availability, integrity, authentication, non-repudiation, confidentiality), results are not always as expected. To take the CLI usability advantages to graphical versions is a constant challenge. This work presents a study about usability factors in legacy CLI, identifies which ones play a significant role and obtains statistical correlations between them, uses some basic concepts from the cognitive sciences to clarify and suggest strategies to do a better graphical interface design in terms of user experience and usability.