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Web applications are needed as a solution to the use of internet technology that is easy to use and capable of displaying information that is rich in content, cost-effective, and accessible. In the second quarter of 2020, Wearesocial released information that around 4.54 billion people in the world used the internet with 59% penetration. People become very dependent on the internet and technology. This condition was also triggered by the Covid-19 pandemic. One thing that becomes an issue on website application security is internet attacks on website platforms and the vulnerability. One type of attack or security threat that often arises and occurs is Cross-Site Scripting (XSS). XSS is one of the Top 10 Open Web Application Security Projects (OWASP) list. Several alternatives can be used to prevent cyberattack like OWASP Security Shepherd. The OWASP Security Shepherd project allows users to learn or develop their manual penetration testing skills. In this research, there are several case examples of challenges that we can use as a simulation of the role of OWASP Security Shepherd to detect this XSS. The purpose of this paper is to conduct a brief and clear review Indonesian Journal of Information Systems (IJIS) Vol. 3, No. 2, February 2021 150 Wibowo, Sulaksono (Web Vulnerability Through Cross Site Scripting (XSS) Detection with OWASP Security Shepherd) of technology on OWASP Security Shepherd. This technology was chosen as an appropriate and inexpensive alternative for users to ward XSS attacks.