Annotation: The issue of increasing the confidentiality and stealth of users on the Internet is the most pressing issue of the day. One way to increase the secrecy of using Internet services is to install the Tor software, which protects itself from the "data flow analysis" is a type of network surveillance that threatens the privacy of users, the confidentiality of business contacts and communications implemented through routing network traffic over a distributed network of servers running volunteers from around the world that does not allow the external observer to monitor the user's Internet connection, find out which sites were visited, and also does not allow the site to know the physical location of the user. However, the software in question has vulnerabilities that result in the loss of personal user freedom. The author, through the application of general scientific methods such as analysis and synthesis, identified a list of vulnerabilities and their importance for the confidentiality of the Tor software. The author carried out the simulation of the Tor software by devices of the experimental environment and the construction of experimental procedures based on the used mathematical apparatus of the Markov chains. The results of the experiment indicate the necessity to determine the validity of the model for analysis of the anonymity protocol. In the course of this research, an algorithm for testing the anonymity of Tor software users was developed, which allows to identify possible sources of personal information of users. The effectiveness of the proposed modeling trust algorithm was demonstrated by calculating the value of a training set of data necessary for outputting a wireless access protocol, a proxy through Tor.
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