Today, the automation of technological and business processes of an enterprise is one of the key trends in the development of information and communication technologies. As part of the development of management methodology and organization of services in this area, Helpdesk and Ser-viceDesk user support systems are becoming increasingly popular. However, most existing solutions do not consider the vulnerabilities of the TCP/IP protocol stack as well as the imperfection of software and operating systems, which often complicates the activities of information technology departments by loading them with routine work. This article presents the development of an automated system of network and system administration of Windows and Linux family operating systems, which includes the Helpdesk and ServiceDesk solutions functionality. The signature method of the system operation with the identification of the correlation of events is reviewed. An original approach to creating a knowledge base of the system is described. The solution was implemented using a platform for automated deployment and management of applications in a virtualization environment, which provides an additional level of reliability and fault tolerance. An algorithm for checking third-party software solutions for suspicious malicious activity is proposed, providing a qualitative analysis of the object being investigated: whether functions undeclared by the developer are present, whether any information is being sent to third parties, etc. A comprehensive approach to the management of the enterprise network infrastructure is presented. In order to ensure information security of network communications, encapsulated secure virtual communication channels were used. To ensure the confidentiality of data on the client side, the AES-256 encryption algorithm was used. The proposed approaches are recommended for corporate computer networks which include ten or more hosts operating on the basis of the TCP / IP protocol stack and Windows / Linux family operating systems.