4 min read

This is Part 2 of the interview with our two Kali Linux experts, Wolf Halton, and Bo Weaver, on using Kali Linux for pentesting. In their section, we talk about the role of pentesting in cybersecurity.

Previously, the authors talked about why Kali Linux is the premier platform for testing and maintaining Windows security. They talked about the advantages and disadvantages for using Kali Linux for pentesting. There also talked about their love for the Kali platform. Wolf says, “Kali is a stable platform, based upon a major distribution with which I am very familiar.  There are over 400 security tools in the Kali repos, and it can also draw directly from the Debian Testing repos for even more tools.
Here are a few more questions, we asked them about what they think about pentesting in cybersecurity, in general.

Can you tell us about the role of pentesting in cybersecurity? According to you, how has pentesting improved over the years?

Bo Weaver: For one thing, pentesting has become an accepted and required practice in network security.  I do remember the day when the attitude was “It can’t happen here. so why should you break into my network?  Nobody else is going to.” Network security, in general, wasn’t even thought by most companies and spending money on network security was seen as a waste.


The availability of tools has also grown in leaps and bounds.  Also, the availability of documentation on vulnerabilities and exploits has grown, and the awareness in the industry of the importance of network security has grown.

Wolf Halton: The tools have gotten much more powerful and easier to use.  A pentester will still be more effective if they can craft their own exploits, but they can now craft it in an environment of shared libraries such as Metasploit, and there are stable pentesting platforms like Kali Linux Rolling (2018) that reduces the learning curve to being an effective pentester.

Pentesting is rising as a profession along with many other computer-security roles.  There are compliance requirements to do penetration tests at least annually or when a network is changed appreciably.

What aspects of pentesting do you feel are tricky to get past? What are the main challenges that anyone would face?

Bo Weaver: Staying out of jail.  Laws can be tricky. You need to know and fully understand all laws pertaining to network intrusion for both, the State you are working in and the Federal laws.  In pen testing, you are walking right up to the line of right and wrong and hanging your toes over that line a little bit. You can hang your toes over the line but DON’T CROSS IT!  Not only will you go to jail but you will never work in the security field again unless it is in some dark corner of the NSA.

Never work without a WRITTEN waiver that fully contains the “Rules of Engagement” and is signed by the owner or “C” level person of the company being tested.

Don’t decide to test your bank’s website even if your intent is for good.  If you do find a flaw and report it, you will not get a pat on the back but will most likely be charged for hacking.  Especially banks get real upset when people poke at their networks. Yes, some companies offer Bug Bounty programs. These companies have Rules of Engagement posted on their site along with a waiver to take part in the program.  Print this and follow the rules laid out.

Wolf Halton: Staying on the right side of the law.  Know the laws that govern your profession, and always know your customer.  Have a hard copy of an agreement that gives you permission to test a network.  Attacking a network without written permission is a felony and might reduce your available career paths.

Author Bio

Wolf Halton is an Authority on Computer and Internet Security, a best selling author on Computer Security, and the CEO of Atlanta Cloud Technology. He specializes in—business continuity, security engineering, open source consulting, marketing automation, virtualization and data center restructuring, network architecture, and Linux administration.
Bo Weaver is an old school ponytailed geek. His first involvement with networks was in 1972 while in the US Navy working on a R&D project called ARPA NET. Bo has been working with and using Linux daily since the 1990’s and a promoter of Open Source. (Yes, Bo runs on Linux.) He now works as the senior penetration tester and security researcher for CompliancePoint a Atlanta based security consulting company.

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