Penetration testing tools try to exploit vulnerabilities using proven attack methods, allowing you to see how your defenses perform and to identify any gaps or misconfigurations. A robust security program can't operate on good practices and faith alone—you need to test and exercise your defenses to ensure they're up to the task. The best way to do this is by simulating real-world attacks.
The availability of penetration testing tools, both open source and paid, lowers the barrier for testing and means you can find the best in-house tool for your abilities without having to rely on pricey, infrequent third-party tests to assess the strength of your security programs. Adding penetration testing tools to your arsenal can serve many purposes, including:
Good vulnerability management practices help prioritize which vulnerabilities you should mitigate; penetration testing tools, in turn, validate whether these vulnerabilities pose a threat, saving you even more time and resources. Pen testing tools will try to exploit identified vulnerabilities using real-world attack methods, providing a useful proof point regarding whether a vulnerability is exploitable in your environment or not.
Considering the time that goes into installing, configuring, and maintaining security tools and programs in a corporate environment, you want to be sure that everything you've put in place—from password security measures and policies to intrusion detection/intrusion prevention systems—will hold up in an attack scenario. This goes for the human factor, too; better to run your security team through a fire drill simulation than to test them for the first time during a real attack.
Chances are there are several mandated security compliance regulations in your industry, and many major regulations—including PCI DSS—require frequent penetration tests. Different compliance measures may have different requirements around how the test should be conducted and how frequently, so do your diligence to understand what’s required for the regulations that impact you.
When evaluating penetration testing solutions, consider the following tips to get the most out of your investment.
A lot of penetration testing tasks can be successfully automated without losing effectiveness. Does the tool you're considering offer robust automation capabilities? The more menial steps you can automate, the more your team can focus on tasks requiring their skill and attention. This is especially key if weighing the benefit of purchasing a paid solution against an open source or free tool; time is money, and automation is where you'll see the greatest efficiency and cost savings over time.
As mentioned above, automation is a key time-saving feature that can free up teams to focus on more skilled work. It's crucial that your team can take over and do a technical deep dive when needed. A veteran pen tester doesn't need wizards or automated tests, and they may want to get right into the code and get working. Be sure to evaluate whether your penetration testing tool will give them the leeway to do this.
Not all penetration testing tools simulate the same attacks that real-world attacks do. It sounds a bit illogical, but you do want to make sure your pen testing tool will test your defenses the same way an attacker might, and not "go easy" on them using simulations that aren't realistic. Your pen testing tools should utilize exploits and techniques used in the real world by actual attackers to be sure you're putting your defenses through their paces.
If you have more than one staff member using a penetration testing tool, you'll want to allow for easy collaboration and data sharing. Any data sets (like credentials) that one tester gains access to should be shared with other testers easily within the pen testing tool to make sure the test is as effective as possible.
In addition to the insights gathered during the pen test, a significant amout of data will also be generated. This is all well and good for your technical teams, but often the results need to be read and understood by security stakeholders who may not have technical expertise. A robust pen testing tool should also provide reporting capabilities to translate important details into easily understandable trends and key takeaways.