This report presents a detailed ethical hacking case study, focusing on the process of system compromise and the retrieval of five flags within a simulated environment. The project involves a defined methodology for network penetration, including vulnerability assessment and exploitation techniques. The report outlines each attack run, detailing the results and providing recommendations for system defense. Key aspects of the study include the utilization of a TCP port scanner and a password cracker, both of which are implemented and documented within the report. The methodology follows a systematic approach, beginning with reconnaissance and progressing to the exploitation of identified vulnerabilities. The report also includes the source code for the developed tools, ensuring repeatability and providing insights into their functionality. The analysis covers web server exploitation, web shell detection, password cracking methods, TCP port scanning, and privilege escalation techniques. The findings emphasize the importance of robust security measures and offer actionable insights into mitigating network security risks. The ethical hacking case study aims to simulate real-world scenarios to enhance understanding of system vulnerabilities and the corresponding defensive strategies.