The continuous outspread and rising popularity of the internet nowadays has resulted in successive breakthroughs on multiple fields of human life. E-commerce, e-banking, social networking and message exchanging are only some of the unlimited services that modern web applications offer and consist an inextricable part of human everyday life in the 21st century.One of the most vital needs of the contemporary web is that of security. Web application development and continuous maintenance is a repetitive and sometimes painful process that demands constant validation of the offered functionality in the desired manner and with the desired result, e.g. with no bugs, and that no vulnerabilities are left to be exploited, as well. The present diploma thesis aims to contribute to the combination of the automated functional and security testing execution, for enhanced vulnerability detection. Towards this direction, a web application was developed, that applies functional and security testing on other web applications in order to reveal as many of their vulnerabilities as possible, by employing a state-of-the-art penetration tool. The developed application analyses the results and visualizes them into comparative lists and graphical charts, providing app security insights over time.