One of the primary concerns of data security specialists is to mitigate insider threats and prevent data leaks. Often, unfortunately, insider threats go unnoticed. In most cases, the longer such activity goes unnoticed, the greater the resulting damages are likely to be. This paper provides an overview of the basic data exfiltration techniques that deal with file structures and were utilized in multiple scenarios in an attempt to bypass a Data Loss Prevention system. Details show which of the scenarios have been detected and which have not been by the Data Loss Prevention system. The paper also proposed solutions for the undetected scenarios.