This paper considers the problem of violation of information security components such as confidentiality and availability in the event of a computer user's residual information. Analyze the requirements of regulators and mechanisms to be applied in the organization to monitor the residual information or its destruction.Approach to monitoring and auditing residual information on the user's computer, which allows monitoring the residual information in certain areas proposed. Approach allows us to identify the detected information and rank it according to the degree of criticality, as well as calculate the risk of leakage and its potential to develop recommendations aimed at its reduction. The proposed approach is formally described and automated in a software system.