Information security of critical infrastructure is important task for every country, organizations, cities, governments. This problem is complex, have many aspects; information about the problem is distributed among many sources, fragmentary, have various degree of reliability, possible discrepancy, varying in time, possible bias, etc. The paper considers the possibilities of applying the technology of assessment and monitoring of complex processes of ensuring information security in the task of sustainable development of the critical infrastructure. The structure of stability model of the critical infrastructure is proposed. Possible scenarios for the system of information security assessment and monitoring and the analytical possibilities of the technology that uses two poles: the human intellect (experts) and artificial intelligence are discussed.