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S I M U L A T E D   P E N E T R A T I O N   T E S T

Penetration testing is the pinnacle for most of us, and 
successfully bypassing an organization’s defenses dur-
ing a penetration test is one of our most rewarding 
experiences. In this chapter, we’ll pull together what 
you’ve learned in previous chapters as we simulate a 
complete penetration test. You will be re-creating steps 
that you’ve seen in previous chapters, so most of what 
is shown here should be familiar.

Before you begin, download and install Metasploit’s vulnerable Linux 

virtual machine called 


. (You can find it at 



.) Metasploitable was created to train indi-

viduals to use Metasploit for successful exploitation. Follow the directions on 
the site to install Metasploitable, and then power it on. We’ll be running the