In today’s world, the volume of cyber attacks grows every year. These attacks can cause many people or companies high financial losses or loss of private data. One of the most common types of attack on the Internet is a DoS (denial-of-service) attack, which, despite its simplicity, can cause catastrophic consequences. A slow DoS attack attempts to make the Internet service unavailable to users. Due to the small data flows, these attacks are very similar to legitimate users with a slow Internet connection. Accurate detection of these attacks is one of the biggest challenges in cybersecurity. In this paper, we implemented our proposal of eleven major and most dangerous slow DoS attacks and introduced an advanced attack generator for testing vulnerabilities of protocols, servers, and services. The main motivation for this research was the absence of a similarly comprehensive generator for testing slow DoS vulnerabilities in network systems. We built an experimental environment for testing our generator, and then we performed a security analysis of the five most used web servers. Based on the discovered vulnerabilities, we also discuss preventive and detection techniques to mitigate the attacks. In future research, our generator can be used for testing slow DoS security vulnerabilities and increasing the level of cyber security of various network systems.