From The Penetration Testing Execution Standard
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This section describes the methodology and issues that the exploitation phase should cover.
Following is an image depicting the main branches of the corresponding mindmap:
Exploitation.png

Purpose

The exploitation phase of a penetration test focuses solely on establishing access to a system or resource by bypassing security restrictions. If the prior phase, vulnerability analysis was performed properly, this phase should be well planned and a precision strike.. The main focus is to identify the main entry point into the organization and to identify high value target assets.

If the vulnerability analysis phase was properly completed, a high value target list should have been complied. Ultimately the attack vector should take into consideration the success probability and highest impact on the organization.

Countermeasures

Countermeasures are defined as preventative technology or controls that hinder the ability to successfully complete an exploit avenue. This technology could be a Host Based Intrusion Prevention System, Security Guard, Web Application Firewall, or other preventative methods. When performing an exploit, several factors should be taken into consideration. In the event of a preventative technology, a circumvention technique should be considered. In circumstances when this is not possible, alternative exploit methods should be considered.

Overall, the purpose is to remain stealth when attacking the organization, if alarms are tripped the level of the assessment could be diminished. If at all possible, the countermeasures should be enumerated prior to triggering the exploit. This could be done through doing dry runs of the attack or enumerating the technology.

Evasion

Evasion is the technique used in order to escape detection during a penetration test. This could be circumventing a camera system as to not be seen by a guard, obfuscating your payloads to evade Intrusion Detection Systems (IDS) or Intrusion Prevention Systems (IPS) or encoding requests/responses to circumvent web application firewalls. Overall, the need to identify a low risk scenario for evading a technology or person should be formulated prior to the exploit.

Precision Strike

The main focus of a penetration test is to simulate an attacker in order to represent a simulated attack against the organization. The value brought through a penetration test is generally not through smash and grab techniques where the attacks are noisy in nature and in an attempt to try every exploit. This approach may be particularly useful at the end of a penetration test to gauge the level of incident response from the organization, but in most cases the exploitation phase is a accumulation of specific research on the target.

Customized Exploitation Avenue

Every attack will typically not be the same in how the exploitation avenue occurs. In order to be successful in this phase, the attack should be tailored and customized based on the scenario. For example, if a wireless penetration test is occurred, and a specific technology is in use, these need to be identified and attacked based on what technologies are in place. Having a clear understanding of each scenario and the applicability of an exploit is one of the most important aspects of this phase of the penetration test.

Tailored Exploits

In a number of occasions the exploits that are public on the Internet may need some work in order to successfully complete. In most cases, if an exploit is designed for Windows XP SP2, specific modifications to the exploit will be required in order for the attack to be successful via Windows XP SP3. The penetration tester should have the knowledge in place to be able to customize an exploit and the ability to change on the fly in order to successfully complete the attack.

Zero-Day Angle

In most cases, the zero-day angle is often a last resort for most penetration testers. This type of attack often represents a highly advanced organization that can handle a focused attack against the organization through normal attack methods. In certain scenarios research may be conducted in order to reverse engineer, fuzz, or perform advanced discovery of vulnerabilities that have not been discovered. In the event this type of attack is applicable, ensure that the environment to the best of the attackers knowledge is reproduced to include countermeasure technology.

In order for zero-day exploits to be successful (or any exploit for that matter), having the same operating system, patches, and countermeasures is highly important on success. Sometimes this information may not be available based on the level of access or enumeration that has occurred.

Example Avenues of Attack

In any scenario, the attacks should consist based on the scenario that is within scope of the engagement. Below is a list of several attack avenues to consider based on scenario but is by no means a comprehensive list.

Web Application Attacks Social-Engineering Physical Attack Avenues Memory Based Exploits (i.e. buffer/heap overflows, memory corruptions, use-after-free). Man in the Middle VLAN Hopping USB/Flash Drive deployment Reverse Engineering Zero-Day Angle Attacking the user Encryption Cracking Graphics Processing Unit (GPU) Cracking Traffic Analysis Firewire Routing protocols Phishing with Pretexting Employee Impersonation

Again, these examples are only basic avenues for attack based on the scenario you are performing for the organization. The value from a penetration test comes from creativity and the ability to identify exposures and exploit them in a precise manner.

Overall Objective

In the pre-engagement interaction phase with the customer, a clear definition of the overall objectives of the penetration test should have been communicated. In the case of the exploitation phase, the biggest challenge is identifying the least path of resistance into the organization without detection and having the most impact on the organizations ability to generate revenue.

By performing the prior phases properly, a clear understanding of how the organization functions and makes money should be relatively understood. From the exploitation phase and into the post-exploitation phase, the attack vectors should rely solely on the mission of circumventing security controls in order to represent how the organization can suffer substantial losses through a targeted attack against the organization.