This paper is intended to explain several Metasploit approaches to exploit the vulnerable Windows 2003 server operating system, especially through msfconsole and msfcli modules, and demonstrates how to access the target computer in a comprehensive hacking life-cycle manner. Metasploit is quite useful in penetration testing, in terms of detecting vulnerabilities in the target Windows 2003 operating system, as well as for exploiting its loopholes. Metasploit could be utilized by both offensive and defensive professionals.