How to Perform a Penetration Test

by | How Tos

Penetration Testing Definition

A penetration test, which is often shortened to “pen test,” is essentially a fake cyberattack. It is conducted by trained cybersecurity engineers, in hopes of revealing any vulnerabilities that the target may have.

3 Types of Penetration Tests

Typically pen tests fall in one of three categories:

1. Black Box Pen Test.

This is a test that is designed not only to identify gaps and vulnerabilities, but also to test the response capabilities of the target. Only top-level management is aware of the test, while the IT and cybersecurity teams are kept in the dark. As far as they know, this is not a drill.

2. White Box Pen Test.

As you might guess, this is the opposite of the black box test above; everyone in the organization knows that the test is coming. Although it is less “real life,” it is very important and sets the ground for further testing and training. White box tests are also useful in situations where a black box test cannot be performed due to operational and security constraints.

3. Gray Box Pen Test.

Yes, this type sits somewhere between the black box and the white one! In this case, some members of the organization are aware that the test is coming, while others are not. The goal, on top of the vulnerability and gap detection, is to test the reaction of various departments, for example communications, HR, legal, etc.

Penetration Test Basic Steps

Irrespective of which type of test will be conducted, proper preparation and scoping is key.

1. Determine the infrastructure being tested.

What is the goal? What systems are being tested? Which departments will be affected? All these questions are part of the scoping phase of a pen test and need very careful consideration.

Remember: a pen test may be a simulated attack, but it is an attack nonetheless and may have inadvertent consequences if not planned right.

Once the scope of the test is clear, the next step typically involves reconnaissance on the target infrastructure. Reconnaissance is part of the test itself, since it will reveal if the organization has enough perimeter protection to detect someone attempting to perform reconnaissance by sniffing on open ports, scanning the IP addresses, etc.

2. Conduct vulnerability identification.

Can we get access to the network? Is a server unpatched? A service open? A credential that has expired? A good test will scan for both known and unknown vulnerabilities by stretching the targets defense systems and attempting to bypass them, or even use them against their target.

3. Exploit vulnerable systems.

Once vulnerabilities have been identified, the next step is taking advantage of them by exploiting them and gaining access to the systems. Once access is in place, the next thing that the tester will do is create back doors and credentials that will allow the tester to maintain the access into the infrastructure.

4. Start remediation steps.

The results of the test are then presented to the various stakeholders along with specific remediation steps. Typically, the test is repeated, to confirm that the remediation has worked and the organization is safe.

Do you need to perform pen tests in your environment? Let us know, and we can help you make the most out of them, plug any gaps, and ensure your cybersecurity resilience.


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