This case study delves into the realm of ethical hacking, focusing on infiltrating a system to achieve root-level privileges. The project revolves around five flags, each representing a milestone in the system compromise. The report outlines the defined methodology and testing log, covering key areas such as web servers, web shells, password cracking, and the use of the TCP port scanning tool NMAP. The study includes practical steps, such as identifying IP addresses, exploiting web server vulnerabilities, utilizing web shells for remote access, cracking passwords using Hashcat, and employing NMAP for TCP port scanning. Furthermore, it discusses privilege escalation techniques within a Linux environment. The report concludes with results and recommendations, emphasizing the importance of ethical hacking in preventing illegal hacking threats and protecting organizations' networks and systems. The student document is available on Desklib, a platform providing study tools and resources for students.