Decide What You Want
When an organization is getting ready to pay for an outside group to come in for a penetration test, executives might be tempted to answer the question, "What do we want them to test?" with a simple, "Everything, of course!" Giving in to that temptation, though, can be a grave mistake.
Penetration tests should be seen as targeted exercises. That target can, of course, be large: A pen test focusing on the network perimeter, for example, could cover a lot of cyber territory. But that territory wouldn't include the organization's application servers. In order to get the most from a third-party pen test, it's important to start with a clear idea of what you want the pen test to tell you.
Among the questions to ask yourself: Why are you performing the pen test? Is it to answer questions about your security? Is it to check a box for regulators, auditors, or insurance underwriters? Are you trying to find out what went wrong in the most recent breach of your security perimeter? Each of these will have its own set of parameters and processes. And each will return its own set of data and conclusions.
It's critical that you have a clear understanding of the pen test's purpose and that you express that purpose to the pen testers clearly. Make sure they understand what you've told them and that the scope of the test is agreed to by both sides. Once the understanding is reached, put it into writing.
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