Book Image

Mastering Kali Linux for Advanced Penetration Testing - Third Edition

By : Vijay Kumar Velu, Robert Beggs
Book Image

Mastering Kali Linux for Advanced Penetration Testing - Third Edition

By: Vijay Kumar Velu, Robert Beggs

Overview of this book

This book takes you, as a tester or security practitioner, through the reconnaissance, vulnerability assessment, exploitation, privilege escalation, and post-exploitation activities used by pentesters. To start with, you'll use a laboratory environment to validate tools and techniques, along with an application that supports a collaborative approach for pentesting. You'll then progress to passive reconnaissance with open source intelligence and active reconnaissance of the external and internal infrastructure. You'll also focus on how to select, use, customize, and interpret the results from different vulnerability scanners, followed by examining specific routes to the target, which include bypassing physical security and the exfiltration of data using a variety of techniques. You'll discover concepts such as social engineering, attacking wireless networks, web services, and embedded devices. Once you are confident with these topics, you'll learn the practical aspects of attacking user client systems by backdooring with fileless techniques, followed by focusing on the most vulnerable part of the network – directly attacking the end user. By the end of this book, you'll have explored approaches for carrying out advanced pentesting in tightly secured environments, understood pentesting and hacking techniques employed on embedded peripheral devices.
Table of Contents (21 chapters)
Title Page
About Packt

The testing methodology

Methodologies rarely consider why a penetration test is being undertaken or which data is critical to the business and needs to be protected. In the absence of this vital first step, penetration tests lose focus.

Many penetration testers are reluctant to follow a defined methodology, fearing that it'll hinder their creativity in exploiting a network. Penetration testing fails to reflect the actual activities of a malicious attacker. Frequently, the client wants to see whether you can gain administrative access to a particular system (Can you root the box?). However, the attacker may be focused on copying critical data in a manner that does not require root access or cause a denial of service.

To address the limitations inherent in formal testing methodologies, they must be integrated in a framework that views the network from the perspective of an attacker, the kill chain.

In 2009, Mike Cloppert of Lockheed Martin CERT introduced the concept that is now known as the attacker kill chain. This includes the steps taken by an adversary when they are attacking a network. It does not always proceed in a linear flow as some steps may occur in parallel. Multiple attacks may be launched over time at the same target, and overlapping stages may occur at the same time.

In this book, we've modified Cloppert's kill chain to more accurately reflect how attackers apply these steps when exploiting networks, application, and data services.

The following diagram shows a typical kill chain of an attacker:

A typical kill chain of an attacker can be described as follows:

  • Explore or reconnaissance phase: The adage, reconnaissance time is never wasted time, adopted by most military organizations, acknowledges that it is better to learn as much as possible about an enemy before engaging them. For the same reason, attackers will conduct extensive reconnaissance of a target before attacking. In fact, it is estimated that at least 70 percent of the work effort of a penetration test or an attack is spent conducting reconnaissance! Generally, they will employ two types of reconnaissance:
    • Passive: This does not directly interact with the target in a hostile manner. For example, the attacker will review the publicly available website(s), assess online media (especially social media sites), and attempt to determine the attack surface of the target. One particular task will be to generate a list of past and current employee names. These names will form the basis of attempts to brute force or guess passwords. They will also be used in social engineering attacks. This type of reconnaissance is difficult, if not impossible, to distinguish from the behavior of regular users.
    • Active: This can be detected by the target but it can be difficult to distinguish most online organizations' faces from the regular backgrounds. Activities occurring during active reconnaissance include physical visits to target premises, port scanning, and remote vulnerability scanning.
  • Delivery phase: Delivery is the selection and development of the weapon that will be used to complete the exploit during the attack. The exact weapon chosen will depend on the attacker's intent as well as the route of delivery (for example, across the network, via wireless, or through a web-based service). The impact of the delivery phase will be examined in the second half of this book.
  • Exploit or compromise phase: This is the point when a particular exploit is successfully applied, allowing attackers to reach their objective. The compromise may have occurred in a single phase (for example, a known operating system vulnerability was exploited using a buffer overflow), or it may have been a multiphase compromise (for example, an attacker physically accessed premises to steal a corporate phone book. The names were used to create lists for brute force attacks against a portal logon. In addition, emails were sent to all employees to click on an embedded link to download a crafted PDF file that compromised their computers). Multiphase attacks are the norm when a malicious attacker targets a specific enterprise.
  • Achieve phase – Action on the Objective: This is frequently, and incorrectly, referred to as the exfiltration phase because there is a focus on perceiving attacks solely as a route to steal sensitive data (such as login information, personal information, and financial information); it is common for an attacker to have a different objective. For example, a business may wish to cause a denial of service in their competitor's network to drive customers to their own website. Therefore, this phase must focus on the many possible actions of an attacker. One of the most common exploit activity occurs when the attackers attempt to improve their access privileges to the highest possible level (vertical escalation) and to compromise as many accounts as possible (horizontal escalation).
  • Achieve phase – Persistence: If there is value in compromising a network or system, then that value can likely be increased if there is persistent access. This allows attackers to maintain communications with a compromised system. From a defender's point of view, this is the part of the kill chain that is usually the easiest to detect.

Kill chains are metamodels of an attacker's behavior when they attempt to compromise a network or a particular data system. As a metamodel, it can incorporate any proprietary or commercial penetration testing methodology. Unlike the methodologies, however, it ensures a strategic-level focus on how an attacker approaches the network. This focus on the attacker's activities will guide the layout and content of this book.