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11.2.3. Traditional Penetration Test‌

A traditional penetration test has become a difficult item to define, with many working from dif- ferent definitions, depending on the space they operate in. Part of this market confusion is driven by the fact that the term “Penetration Test” has become more commonly used for the previously mentioned compliance-based penetration test (or even a vulnerability assessment) where, by de- sign, you are not delving too deep into the assessment because that would go beyond the minimum requirements.

For the purposes of this section, we will side-step that debate and use this category to cover as- sessments that go beyond the minimum requirements; assessments that are designed to actually improve the overall security of the organization.

As opposed to the previously-discussed assessment types, penetration tests don’t often start with a scope definition, but instead a goal such as, “simulate what would happen if an internal user is compromised” or, “identify what would happen if the organization came under focused attack by an external malicious party.” A key differentiator of these sorts of assessments is that they don’t just find and validate vulnerabilities, but instead leverage identified issues to uncover the worst- case scenario. Instead of relying solely on heavy vulnerability scanning toolsets, you must follow up with validation of the findings through the use of exploits or tests to eliminate false positives and do your best to detect hidden vulnerabilities or false negatives. This often involves exploiting



vulnerabilities discovered initially, exploring the level of access the exploit provides, and using this increased access as leverage for additional attacks against the target.

This requires critical review of the target environment along with manual searching, creativity, and outside-the-box thinking to discover other avenues of potential vulnerability and ultimately using other tools and tests outside those found by the heavier vulnerability scanners. Once this is completed, it is often necessary to start the whole process over again multiple times to do a full and complete job.

Even with this approach, you will often find that many assessments are composed of different phases. Kali makes it easy to find programs for each phase by way of the Kali Menu:

• Information Gathering: In this phase, you focus on learning as much as possible about the target environment. Typically, this activity is non-invasive and will appear similar to stan- dard user activity. These actions will make up the foundation of the rest of the assessment and therefore need to be as complete as possible. Kali’s Information Gathering category has dozens of tools to uncover as much information as possible about the environment being assessed.

• Vulnerability Discovery: This will often be called ”active information gathering”, where you don’t attack but engage in non-standard user behavior in an attempt to identify potential vulnerabilities in the target environment. This is where the previously-discussed vulnera- bility scanning will most often take place. The programs listed in the Vulnerability Analysis, Web Application Analysis, Database Assessment, and Reverse Engineering categories will be useful for this phase.

• Exploitation: With the potential vulnerabilities discovered, in this phase you try to exploit them to get a foothold into the target. Tools to assist you in this phase can be found in the Web Application Analysis, Database Assessment, Password Attacks, and Exploitation Tools categories.

• Pivoting and Exfiltration: Once the initial foothold is established, further steps have to be completed. These are often escalating privileges to a level adequate to accomplish your goals as an attacker, pivoting into other systems that may not have been previously acces- sible to you, and exfiltrating sensitive information from the targeted systems. Refer to the Password Attacks, Exploitation Tools, Sniffing & Spoofing, and Post Exploitation categories to help with this phase.

• Reporting: Once the active portion of the assessment is completed, you then have to docu- ment and report on the activities that were conducted. This phase is often not as technical as the previous phases, however it is highly important to ensure your client gets full value from the work completed. The Reporting Tools category contains a number of tools that have proven useful in the reporting phase.

In most cases, these assessments will be very unique in their design as every organization will operate with different threats and assets to protect. Kali Linux makes a very versatile base for

these sorts of assessments and this is where you can really take advantage of the many Kali Linux customization features. Many organizations that conduct these sorts of assessments will maintain highly customized versions of Kali Linux for internal use to speed up deployment of systems before a new assessment.

Customizations that organizations make to their Kali Linux installations will often include:

• Pre-installation of commercial packages with licensing information. For instance, you may have a package such as a commercial vulnerability scanner that you would like to use. To avoid having to install this package with each build, you can do it once21 and have it show up in every Kali deployment you do.

• Pre-configured connect-back virtual private networks (VPN). These are very useful in leave- behind devices that allow you to conduct ”remote internal” assessments. In most cases, these systems will connect back to an assessor-controlled system, creating a tunnel that the assessor can use to access internal systems. The Kali Linux ISO of Doom22 is an example of this exact type of customization.

• Pre-installed internally-developed software and tools. Many organizations will have private toolsets, so setting these up once in a customized Kali install23 saves time.

• Pre-configured OS configurations such as host mappings, desktop wallpaper, proxy settings, etc. Many Kali users have specific settings24 they like to have tweaked just so. If you are going to do a re-deployment of Kali on a regular basis, capturing these changes makes a lot of sense.

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