Tech Insight: 3 Factors To Assess Before Doing Your Own Penetration Testing

Training: Training the newly designated pen tester -- or, if you're lucky, a whole pen-testing team -- is the next item on the cost sheet. Time needs to be set aside to attend training either online or at a conference. Online courses, like those from Offensive Security, run as little as $500 to several thousand dollars, while a multiday pen-testing course, like SEC 560 Network Penetration Testing and Ethical Hacking from SANS, is $4,300 for six days.

Don't forget about retention issues that can accompany adding increased responsibilities on current employees and training both new and current employees. Competent pen-testing skills are very valuable right now, and you'll need to make sure your pen testers' salaries are reasonably competitive with how much they could make elsewhere.

It's not uncommon for employers to draw up a contract that says the employee must repay part or all of the training expenses if he chooses to leave for another employer within a specific amount of time.

Software: Pen-testing software runs the gamut in terms of cost. Exceptional free tools, like the Metasploit Framework and w3af, are available, but they entail a steeper learning curve compared to a polished commercial solution like Core IMPACT. The differences can be measured in the tens of thousands of dollars and hours versus days to become familiar and reasonably comfortable using the different tools. Determining which software to use will depend on budget, organization size, familiarity of the tools by the pen tester, and technologies used by the target.

Once you've answered the question of whether performing in-house pen testing is cost-effective, you still need to answer the ever important question: Can your team perform a comprehensive test that is objective and doesn't suffer from a myopia that often occurs when the tester is too close to the target organization?

The upside of performing pen testing with an internal team is they are familiar with the organization, the network, where the critical assets are, and the people. They may end up finding chinks in the company's armor quicker than a third-party pen tester because they have the familiarity and will know where to look first.

But the trade-off is an internal pen-testing team may be too familiar and comfortable with the target environment and could overlook common issues that someone from the outside may not. Personal relationships may even impact whether they target specific users for social engineering exercises, like a simulated phishing attack.

Making the decision to staff, train, and maintain an internal pen-testing team is a big one that can have a serious impact on the security of your company -- more than just checking off "YES" on a PCI Self Assessment Questionnaire. It's a good idea to hire a third-party pen-testing firm to follow up on the initial pen tests by the internal team to make sure they're doing a solid job -- and every couple of years thereafter to ensure results are consistent.

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