In this research we present the hybrid model of finding the most critical distribution trajectories of multipath Social engineering attacks, passing through which by the malefactor on a global basis has the topmost degree of probability and will bring the greatest loss to the company. The solution of search problem concerning the most critical trajectories rests upon the assumption that the estimated probabilities of the direct Social engineering attack on user, degree evaluation of documents’ criticality, the estimated probabilities of Social engineering attack’s distribution from user to user are premised on linguistic indistinct variables are already calculated. The described model finds its application at creation when constructing the estimates of information systems users’ safety against Social engineering attacks and promotes well-timed informing of decision-makers on the vulnerabilities which being available in system.