This thesis focuses on security of web applications, which can be measured by the results of penetration testing. In the theoretical section of this study individual methods of how the testing can be performed are outlined. This study then outlines the advantages and disadvantages of automated testing compared to manual testing, and the tools which incorporate automated scanning for security of web applications are scrutinized. Statistics of security risk occurrences found on the Czech Internet are also included. The practical part depicts the creation of a tool for automated testing, written in the most frequently used programming language in web development, that will be able to detect the most common weaknesses. The tool is developed to ...