Penetration Testing a VM

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1. Introduction

A penetration test is performed on a system in order to find security threats. The pen tester carries out the same tests a hacker would do. The hacker is looking for vulnerabilities in the computer and network in order to exploit them and gain access. The pen tester performs the same task but wants to find and fix any security threats without harming or compromising the system. The pen tester has permission to perform vulnerability checkes wheras the hacker does not. (Add more).

2. Configure Backtrack on VM Image Network

In order to run network exploration and web vulnerability tools, Backtrack 5 must be on the same network as the VM image. This is accomplished by changing Backtrack and the VM image to a custom virtual network. In the Virtual Network Editor a network is added which can be customised to allow network connectivity. The network added defaults to Vmnet3. Host only is selected which connects VMs internally in a private network. Use local DHCP service to distribute IP addresses to VMs is selected. The subnet IP and the subnet mask is changed to the VM image network. (See Figure 2-1 below).

Figure 2-1. Custom settings in Virtual Network Editor.

Backtrack and the VM image are now on the same network but the exact IP address of the VM is still unknown. The IP can be found by using a scanning tool like Nmap.

3. Nmap Scan.

A network mapper (Nmap) is an open source tool for network exploration and security auditing. Nmap is used to verify open ports and discover vulnerabilities associated with those open ports.
A basic nmap scan of the entire VM image network will discover all available hosts. The subnet mask 255.255.255.248 only allows 6 hosts, so a rapid scan is expected. The basic nmap com...

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Figure 10-2.9. Password hashes cracked with JTR.

We have successfully found tksies and root's passwords. Access to the server is granted. Follow the steps listed above to complete the mission.

11. Conclusion

Penetration testing a server for vulnerabilities requires a lot of lateral thinking. There is never one defined method to complete different tasks. A good pen tester must be able to recognise crucial information provided such as potential usernames and service vulnerabilities. Nmap is an excellent tool to scan for open ports and reveal vulnerabilities. Nikto was a vital tool in this mission as it provided a way to irrefutably find the usernames on the server. The mission was a good examination of my skillset. It also tested my proficiency and knowledge of the tools. The knowledge gained will help with future missions and make me a better pen tester.

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