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Red-Teaming and Pentesting

Pentesting is an attack on a computer system, done to evaluate the security of the system/network. This test is performed to identify vulnerabilities and the risks they possess.

The 1960's marked the true beginning of the age of computer security. In this chapter, we will cover the methodology of pentesting that is widely used, as well as the red-teaming approach, which is now being adopted across different corporations.

In this chapter, we will cover the following topics:

Pentesting 101
A different approach

Pentesting 101

As we all know, penetration testing follows a standard. There are various standards, such as the Open Web Application Security Project (OWASP), the Open Source Security Testing Methodology Manual (OSSTMM), the Information Systems Security Assessment Framework (ISSAF), and so on. Most of them follow the same methodology, but the phases have been named differently. We will take a look at each of them in the following sections and cover the Penetration Testing Execution Standards (PTES) in detail.

OWASP

OWASP is a worldwide not-for-profit charitable organization that focuses on improving the security of software.

It's a community of like-minded professionals who release software and knowledge-based documentation on application security, covering such subjects as:

Information gathering
Configuration and deployment management testing
Identity management testing
Authentication testing
Authorization testing
Session management testing
Input validation testing
Error handling
Cryptography
Business logic testing
Client-side testing

Open Source Security Testing Methodology Manual (OSSTMM)

As mentioned on their official website, this is a peer-reviewed manual of security testing and analysis, providing verified facts. These facts provide actionable information that can measurably improve your operational security.

The OSSTMM includes the following key sections:

Operational security metrics
Trust analysis
Work flow
Human security testing
Physical security testing
Wireless security testing
Telecommunications security testing
Data networks security testing
Compliance regulations
Reporting with the Security Test Audit Report (STAR)

Information Systems Security Assessment Framework (ISSAF)

ISSAF is not very active, but the guide it has provided is quite comprehensive. It aims to evaluate the information security policy and process of an organization with regard to its compliance with IT industry standards, along with laws and regulatory requirements. The current version of ISSAF is 0.2.

The stages that it covers can be found at https://www.owasp.org/index.php/Penetration_testing_methodologies.

Penetration Testing Execution Standard (PTES)

This standard is the most widely used standard and covers almost everything related to pentesting.

PTES is divided into the following seven phases:

Pre-engagement interactions
Intelligence gathering
Threat modeling
Vulnerability analysis
Exploitation
Post-exploitation
Reporting

Let's take a brief look at what each of these phases involves.

Pre-engagement interactions

These actions involve multiple processes to be carried out before an activity kicks off, such as defining the scope of the activity, which usually involves mapping the network IPs, web applications, wireless networks, and so on.

Once the scoping is done, lines of communication are established across both the vendors and the incident reporting process is finalized. These interactions also include status updates, calls, legal processes, and the start and end dates of the project.

Intelligence gathering

This is a process that is used to gather as much as information as possible about the target. This is the most critical part of pentesting, as the more information we have, the more attack vectors we can plan to perform the activity. In case of a whitebox activity, all this information is already provided to the testing team.

Threat modeling

Threat modeling model depends on the amount of information gathered. Depending on that, the activity can be divided and then performed using automated tools, logical attacks, and so on. The following diagram illustrates an example of a mindmap of a threat model:

Vulnerability analysis

This is a process of discovering flaws that can be used by an attacker. These flaws can be anything ranging from open ports/service misconfiguration to an SQL injection. There are lots of tools available that can help in performing a vulnerability analysis.

These include Nmap, Acunetix, and Burp Suite. We can also see new tools being released every few weeks.

Exploitation

This is a process of gaining access to the system by evading the protection mechanism on the system based on the vulnerability assessment. Exploits can be public, or a zero day.

Post-exploitation

This is a process where the goal is to determine the criticality of the compromise and then maintain access for future use. This phase must always follow the rules of the engagement that is protecting the client and protecting ourselves (covering the tracks as per the activity's requirements).

Reporting

This is one of the most important phases, as the patching of all the issues totally depends on the details presented in the report. The report must contain three key elements:

Criticality of the bug
Steps of reproduction of the bug
Patch suggestions

In summary, the pentest life cycle phases are presented in the following diagram:

A different approach

Let's discuss a different approach: red-teaming. The main objective of red-teaming is to assess and obtain the real level of risk a company has at that moment in time. In this activity, networks, applications, physical, and people (social engineering) are tested against weaknesses.

Red-teaming can also be considered as a simulation of a real-world hack.

Methodology

Red-teaming is based on the PTES standard as the foundation. However, there's much more to it. It can be said that the penetration testing activity is performed with the aim of finding as many vulnerabilities in the given amount of time as possible. However, red-teaming is performed with only one goal and by staying discreet.

The methodology used in a red-team activity involves the following:

Reconnaissance
Compromise
Persistence
Command and control
Privilege escalation
Pivoting
Reporting and cleanup

The following cycle basically repeats for every new piece of information that is found about the client until the goal is met:

How is it different?

Let's look at it with a different perspective to get a clearer picture:

Looking at the preceding diagram, we can see that red-teaming involves using every means to achieve the goals. We can summarize the major difference between red-teaming and pentesting as follows:

Red-teaming involves finding and exploiting only those vulnerabilities that help to achieve our goal, whereas pentesting involves finding and exploiting vulnerabilities in the given scope, which is limited to digital assets
Red-teaming has an extremely flexible methodology, whereas pentesting has fixed static methods
During red-teaming, the security teams of the organizations have no information about it, whereas during pentesting, security teams are notified
Red-teaming attacks can happen 24/7, while pentesting activities are mostly limited to office hours
Red-teaming is more about measuring the business impact of the vulnerabilities, whereas pentesting is about finding and exploiting vulnerabilities.

Key benefits

Target a complex enterprise environment in a Red Team activity

Detect threats and respond to them with a real-world cyber-attack simulation

Explore advanced penetration testing tools and techniques

Description

Red Teaming is used to enhance security by performing simulated attacks on an organization in order to detect network and system vulnerabilities. Hands-On Red Team Tactics starts with an overview of pentesting and Red Teaming, before giving you an introduction to few of the latest pentesting tools. We will then move on to exploring Metasploit and getting to grips with Armitage. Once you have studied the fundamentals, you will learn how to use Cobalt Strike and how to set up its team server. The book introduces some common lesser known techniques for pivoting and how to pivot over SSH, before using Cobalt Strike to pivot. This comprehensive guide demonstrates advanced methods of post-exploitation using Cobalt Strike and introduces you to Command and Control (C2) servers and redirectors. All this will help you achieve persistence using beacons and data exfiltration, and will also give you the chance to run through the methodology to use Red Team activity tools such as Empire during a Red Team activity on Active Directory and Domain Controller. In addition to this, you will explore maintaining persistent access, staying untraceable, and getting reverse connections over different C2 covert channels. By the end of this book, you will have learned about advanced penetration testing tools, techniques to get reverse shells over encrypted channels, and processes for post-exploitation.

What you will learn

Get started with red team engagements using lesser-known methods

Explore intermediate and advanced levels of post-exploitation techniques

Get acquainted with all the tools and frameworks included in the Metasploit framework

Discover the art of getting stealthy access to systems via Red Teaming

Understand the concept of redirectors to add further anonymity to your C2

Get to grips with different uncommon techniques for data exfiltration

What do you get with Print?

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Saibal Dasgupta Mar 06, 2020

Great book for hands on security training. Practical, crisp and clear.

Amazon Verified review

David Dec 07, 2019

The book contains good concept on how to get started in a Red Team Engagment. There is explanation about how to use Metasploit, Empire and Cobalt Strike. If you already know how to play with them, you can definitely skip those chapter. More interesting chapter are in the end. It's an easy read book. However, if you are looking for a deep Red Team attack, this is not the book for that. I have put 3 stars because I didn't learn that much stuff in it. The cheatsheet will be useful for some engagement. There is a lot of screenshot in it and it's not in color (black & white).

Amazon Kunde Jun 14, 2019

für anfänger ist es vielleicht gut....

Arjun Kamble Jan 05, 2019

This book is perfect for those who want to learn hardcore PT skills & wants to reach a Red Teamer level.Stuck at reverse shell? Buy this bookStuck at pivoting? Buy this bookStuck at post exploitation? Buy this bookWant to look for new exploitation tools? Buy this bookWant to learn about infiltration & exfiltration? Buy this bookThis book covers almost all the basic tools and concepts which are required for a Pentester to become a Red Teamer. The authors have done an amazing job here! Kudos to you guys.

Aryan Mishra Jan 04, 2019

If you are having basic understanding of security and want to improve your PT skills, this is the book you should read. This book introduces you to the world of red teaming. Info of some new tools you must hands on. In short it’s worth buying book.

Hands-On Red Team Tactics: A practical guide to mastering Red Team operations

What do you get with Print?

Hands-On Red Team Tactics

Red-Teaming and Pentesting

Pentesting 101

OWASP

Open Source Security Testing Methodology Manual (OSSTMM)

Information Systems Security Assessment Framework (ISSAF)

Penetration Testing Execution Standard (PTES)

Pre-engagement interactions

Intelligence gathering

Threat modeling

Vulnerability analysis

Exploitation

Post-exploitation

Reporting

A different approach

Methodology

How is it different?

Summary

Questions

Further reading

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Hands-On Red Team Tactics: A practical guide to mastering Red Team operations

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