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Perimeter

3/24/2009
05:04 PM
John H. Sawyer
John H. Sawyer
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DIY Pentesting Lab

In Friday's Tech Insight, I provided arguments for creating your own internal security lab and some of the benefits to both the business and the IT security professionals. This week, I want to provide more direction on what you'll need depending on your goal and focus of the lab. Today, we'll be looking at suggestions for security teams looking to learn more about and get their hands dirty wit

In Friday's Tech Insight, I provided arguments for creating your own internal security lab and some of the benefits to both the business and the IT security professionals. This week, I want to provide more direction on what you'll need depending on your goal and focus of the lab. Today, we'll be looking at suggestions for security teams looking to learn more about and get their hands dirty with some in-house penetration testing.Before I get started, I do want to add a small disclaimer. If your organization is looking to begin internal pentesting to meet regulations such as PCI that now require annual pentesting, hire a third party for the first couple of years until your staff is experienced enough. Saving money is good, but not at the expense of cutting corners such as performing pentests in-house with inexperienced personnel.

Now, that said, many organizations faced with PCI regulations will probably find it more economical to develop new or enhance existing skills of current staff to meet this requirement. A security lab designed for this specific purpose is a good idea when coupled with a training course such as SANS Security 560 pentesting and Offensive Security 101. Using the lab, staff can reinforce the skills learned in those courses.

When building a lab focused on internal pentesting, there are two necessities: a good representation of your production network and known vulnerable systems to practice exploiting. Pentesting tools are also necessary but quite numerous and beyond the scope of this blog entry.

First, let's start with the vulnerable systems. Before you can become a good pentester, you need to practice enumerating systems and their services, exploiting them, using them for pivot points to gain deeper access into the network, scouring them for useful information and similar activities. Having vulnerable versions of the current operating systems and services in use on your network is best, but you can also use other exploitable resources.

For example, OldApps.com and Securinfos has vulnerable software available for download that can be used for testing both server and client-side exploits. PaulDotCom has an excellent wiki page on using the Metasploit Framework (MSF) to exploit a vulnerable Icecast server, scan a server from within MSF, pass a windows hash with Incognito and bypass antivirus.

By having a lab network setup similar to your production network, it makes the testing more realistic, but it also makes the building of the lab more complex requiring more hardware and space--something that needs to be weighed cautiously between the cost, benefits and burden to maintain.

Simpler setups can be accomplished either with a single server running multiple virtual machines (VMs) or locally on the trainee's workstation. Either option incurs minimal cost now that there are so many free choices for virtualization such as VMware Server, ESXi and Player; VirtualBox; and Microsoft's Hyper-V.

And finally, if you want to jump right into learning without building VMs, there are Linux-based LiveCDs designed to teach skills in pentesting including enumeration, web exploitation, password cracking, reverse engineering and much more. A few examples include Damn Vulnerable Linux and the De-ICE.net CDs which are bootable CDs designed to be self-contained learning environments.

As you can see, there are many, many different options and things to consider when building a pentesting lab. Ultimately, it comes down to you and your organization's goals. Are you working to build up an internal pentesting team to save money on hiring outside consultants? Need to cut costs until the market turns around which means your training was cut so a lab might help until funds for training are available again?

In my next blog entry, I'll cover lab options and considerations focusing on digital forensics and incident response.

John H. Sawyer is a senior security engineer on the IT Security Team at the University of Florida. The views and opinions expressed in this blog are his own and do not represent the views and opinions of the UF IT Security Team or the University of Florida. When John's not fighting flaming, malware-infested machines or performing autopsies on blitzed boxes, he can usually be found hanging with his family, bouncing a baby on one knee and balancing a laptop on the other. Special to Dark Reading.

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