Penetration tests: 10 tips for a successful program

Penetration tests need to accomplish business goals, not just check for random holes. Here's how to get the most value for your efforts.

By Neil Roiter

November 15, 2010 — CSO —

Why are you performing penetration tests? Whether you're using an internal team, outside experts or a combination of the two, are you simply satisfying regulatory or audit requirements, or do you actually expect to improve enterprise security?

We asked penetration testing experts for guidance on how to improve your program to get the most benefit for your time, money and effort. If you turn to outside expertise, their advice will show you what to expect and demand from consultants. The following 10 tips will show you understand the goal and focus of your testing; develop effective testing strategies; make effective use of your personnel; and make the most effective use of pen test results to remediate issues, improve processes and continuously improve enterprise security posture.

Penetration Test Tip 1: Define Your Goals

Penetration testing—really, all information security activity—is about protecting the business. You are taking on the role of attacker to find the vulnerabilities and exploiting them to determine the risks to the business and making recommendations to improve security based on your findings. Attackers are trying to steal your data—their techniques are a means to an end. So too, penetration testing: It's not about the cool technical things you can do to exploit a vulnerability; it's about discovering where the business risk is greatest.

"If can't express things in terms of my business, you're not providing me value," said Ed Skoudis, founder and senior security consultant at InGuardians. "Don't tell me you've exploited a vulnerability and gotten shell on that box without telling me what that means for my business."

Also see Network stress test tools: dos and don'ts on CSOonline.com

With that understanding, from a more tactical perspective, penetration testing is a good way to determine how well your security policies, controls and technologies are actually working. Your company is investing a lot of money in products, patching systems, securing endpoints etc. As a pen tester, you are mimicking an attacker, trying to bypass or neutralize security controls.

"You're trying to give the company a good assessment if their money is being well spent," said Alberto Solino, founder and director of security consulting services of Core Security.

The goal should not be to simply get a check box for pen testing to meet compliance requirements, such as PCI DSS. Pen tests should be aimed at more than discovering vulnerabilities (vulnerability scanning should be part of a pen testing program but is not a substitute). Unless the testing is part of a sustained program for discovering, exploiting and correcting security weaknesses, your money and effort will have gained you at best that check mark, and at worst, a failed audit by a sharp assessor.


Penetration Test Tip 2: Follow the data

Organizations have limited budget and limited resources for pen testing, regardless of whether you are conducting internal tests, hiring outside consultants or using a combination of both. You can't conduct penetration tests across your entire IT infrastructure, spanning hundreds or thousands of devices, yet pen testers will often be told to try to compromise devices across an extensive range of IP addresses. The result is likely to be the most cursory of testing regimens, yielding little or no value. You can't even expect to conduct vulnerability scans and remediate flaws across a very large number of devices in a reasonable amount of time and at reasonable cost.

"In many cases customers have thousand of IP addresses they want us to pen test," said Omar Khawaja, Global Products Manager, Verizon Security Solutions. "We could run vulnerability tests and see what's most vulnerable, but they may not be the most important to your organization."

Step back and ask, "What am I trying to protect?" What critical data is at risk: credit card data, patient information, personally identifiable customer information, business plans, intellectual property? Where does the information reside? Do you even know every database, every file repository and every log store that contains sensitive data? You may not know, but chances are an attacker will find it.

So, the first critical step is to narrow the scope of pen testing is data discovery: determining which sensitive data is at risk and where it is. Then the task is to play the role of attacker and figure out how to get at the prize. (Read Red team versus blue team for more ideas on this approach.)

"The idea to mimic what a real attacker will do during time frame agreed to with the customer," said Core Security's Solino, "not to find all the possible problems."

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