The relevance of the topic is due to the fact that penetration testing (tests to overcome protection, penetration testing, pentest) is a worldwide popular service in the field of information security. The essence of such work is an authorized attempt to circumvent the existing set of protection means of information system. During testing, the auditor performs the role of an attacker motivated to violate the information security of customer's network. In article, features of penetration testing are thoroughly studied, a detail analysis of existing foreign solutions in the field of penetration testing is performed, a proprietary technique is developed and recommendations for improving the existing techniques are proposed.