Execution of a Penetration Test

Kickoff Meeting

Unless a black box test is called for, it is important to schedule and attend a kickoff meeting, prior to engaging with the client. This is your opportunity not only to confirm your understanding of the client’s needs and requirements but also to get off on the right foot with the client.

It is helpful to remind the client of the purpose of the penetration test: to find as many problems in the allotted time as possible and make recommendations to fix them before the bad guys find them. This point cannot be overstated. It should be followed with an explanation that this is not a cat-and-mouse game with the system administrators and the security operations team. The worst thing that can happen is for a system administrator to notice something strange in the middle of the night and start taking actions to shut down the team. Although the system administrator should be commended for their observation and desire to protect the systems, this is actually counterproductive to the penetration test, which they are paying good money for.

The point is that, due to the time and money constraints of the assessment, the testing team will often take risks and move faster than an actual adversary. Again, the purpose is to find as many problems as possible. If there are 100 problems to be found, the client should desire that all of them be found. This will not happen if the team gets bogged down, hiding from the company employees.

Access During the Penetration Test

During the planning phase, you should develop a list of resources required from the client. As soon as possible after the kickoff meeting, you should receive those resources from the client. For example, you may require a conference room that has adequate room for the entire testing team and its equipment and that may be locked in the evenings with the equipment kept in place. Further, you may require network access. You might request two network jacks, one for the internal network, and the other for Internet access and research. You may need to obtain identification credentials to access the facilities. The team leader should work with the client point of contact to gain access as required.

Managing Expectations

Throughout the penetration test, there will be a rollercoaster of emotions (for both the penetration testing team and the client). If the lights flicker or a breaker blows in the data center, the penetration testing team will be blamed. It is imperative that the team leader remain in constant communication with the client point of contact and manage expectations. Keep in mind this axiom: first impressions are often wrong. As the testing team discovers potential vulnerabilities, be careful about what is disclosed to the client, because it may be wrong. Remember to under-promise and overachieve.

Managing Problems

From time to time, problems will arise during the test. The team may accidentally cause an issue, or something outside the team’s control may interfere with the assessment. At such times, the team leader must take control of the situation and work with the client point of contact to resolve the issue. There is another principle to keep in mind here: bad news does not get better with time. If the team broke something, it is better to dis- close it quickly and work to not let it happen again.

Steady Is Fast

There is an old saying, “steady is fast.” It certainly is true in penetration testing. When performing many tasks simultaneously, it will seem at times like you are stuck in quick- sand. In those moments, keep busy, steadily grinding through to completion. Try to avoid rushing to catch up; you will make mistakes and have to redo things.

External and Internal Coordination

Be sure to obtain client points of contact for questions you may have. For example, after a couple of days, it may be helpful to have the number of the network or firewall administrator on speed dial. During off hours, if the client point of contact has gone home, sending an e-mail or SMS message to them occasionally will go a long way to- ward keeping them informed of progress. On the other hand, coordination within the team is critical to avoid redundancy and to ensure that the team doesn’t miss something critical. Results should be shared across the team, in real time.