The complexity of the Information systems is increasing day by day. This leads to more security vulnerabilities in IT Systems. Attackers use these vulnerabilities to penetrate for the target's system. It is better to find these vulnerabilities in advance before the attacker does. The power of vulnerability assessment is often overlooked. Penetration testing is a set of activities undertaken to identify and exploit vulnerabilities. It helps to verify the effectiveness of the security measures implemented. When the existing penetration test approaches and methods are examined, another issue that is overlooked is that not all steps are performed adequately in the penetration test process. In the environments where penetration tests will be performed, the number of attack vectors may be limited only if progress is made depending on the capabilities of the Penetration Test Specialist and / or some important parts may be missing due to forgetting or lack of ability. In this work, my studies on how to use the comprehensive infiltration test software in cyber defense technology, how to apply more attack vectors and more results can be obtained during the tests with a new perspective and how to automate the detection of social engineering weaknesses with an automated application tool. is located together. Automated test results were compared with the results of the manual tests performed in 7 different environments and the superior parts are indicated in the results section. I also talked about which tools will be used for which purposes and at what stages, and I have automated several steps of penetration testing.

Keywords : Vulnerability Assessment, Adaptive Penetration Test, Automated Application Security, Computer Security And Computer Ethics.