This report provides an evaluation of two password cracking tools, John the Ripper and Rainbow Crack, along with a penetration testing analysis conducted on an e-commerce website for a clothing shop. It discusses password cracking countermeasures, explains the tools, and compares their performance in terms of time and ease of use. The report details the steps involved in using both John the Ripper and Rainbow Crack for password cracking. Furthermore, it outlines the phases of penetration testing, including agreement, planning, scanning, gaining access, maintaining access, exploiting, and evidence collection, emphasizing the importance of identifying and addressing security vulnerabilities to prevent breaches in systems like Linux-based FTP servers. The analysis is centered around a hypothetical scenario involving a clothing shop owner aiming to secure their new e-commerce website.