Recently the attacks on information systems began to occur more frequently and there are serious costs
and the attacks require more time to investigate such crimes. At the same time the share of social engineering attacks
among successful incidents related to the information security violation is growing. For this the general objective of the
research direction is seen as the automated construction of assessments of the user security of information systems against
socio-engineering attacks. One of the tasks within the movement towards this aim is to develop approaches for identifying
the most critical trajectories of complex socio-engineering attacks proliferation performed through the chain of
information system users. To search for such trajectories, the oriented social graphs of employees are used.