Evasion Techniques and Breaching Defenses (PEN-300) is an advanced penetration testing course. Learners who complete the course and pass the exam will earn the OffSec Experienced Pentester (OSEP) certification. This course builds on the knowledge and techniques taught in Penetration Testing with Kali Linux, teaching learners to perform advanced penetration tests against mature organizations with an established security function and focuses on bypassing security mechanisms that are designed to block attacks. The OSEP is one of three certifications making up the OSCE certification along with the OSWE for advanced web attacks and OSED for exploit development.

This chapter covers the fundamental principles of VAPT project planning, management, and governance. It also delves into the People, Process, and Technology (PPT) framework, which helps to clarify the role of individuals, processes, and technology in VAPT practice. The chapter further explores VAPT methodology and approach in detail, equipping Pen testers with an industry-oriented understanding of the practice. With this understanding and an agile approach, Pen testers can execute enterprise-level testing practices smoothly and efficiently.


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The primary aim of this chapter is to provide cyber security professionals and organizations with an in-depth understanding of advanced VAPT approaches and methods. By reading this chapter, you will learn not only about the VAPT approach but also about its standards, frameworks, scope designing, customer engagement, project management, governance, and customer success strategies.

A decade ago, when organizations did not prioritize cyber security, basic technical knowledge was enough to conduct a vulnerability assessment scan using automated tools. However, this approach can now only identify known and technical vulnerabilities. As technology and VAPT methodology have evolved, modernization is crucial. For instance, the attack payload must be advanced and Fully Undetectable (FUD) to bypass security controls effectively. It is essential to have objective-oriented testing approaches that define why a network firewall or web application firewall needs to be bypassed during the audit. Advanced VAPT approaches use more sophisticated tools and techniques to detect and exploit vulnerabilities, offering numerous benefits, as shown in Figure 1.2. 

To ensure timely and comprehensive detection of all vulnerabilities, your risk-based approach must be both agile and advanced. Advanced penetration testing can help you not only detect vulnerabilities but also identify the most effective security controls for your computer infrastructure. Pen testers must possess a comprehensive understanding and skill set to accurately audit key sensitive areas of the business.

The scope of a VAPT exercise should encompass a wide range of assets, including networks, websites, software, wireless networks, mobile applications, APIs, containers, cloud-based services, social platforms, and security devices. In some cases, physical penetration testing may also be necessary to simulate real-world threats and create a robust security ecosystem within the organization.

While many tools with extensive databases exploit known technical vulnerabilities, the manual approach remains the best and most accurate way to exploit business logic flows or logical weaknesses. Some organizations prefer conducting penetration testing in production to assess the effectiveness of their security controls as well.

Kali Linux is the most popular and advanced penetration testing Linux distribution within the cybersecurity industry. Using Kali Linux, a cybersecurity professional will be able to discover and exploit various vulnerabilities and perform advanced penetration testing on both enterprise wired and wireless networks.

Burp Suite is a set of web application penetration testing utilities. Moreover, an integrated platform with various tools that work hand in hand to help detect and exploit vulnerabilities. These tools work seamlessly with each other, from the mapping to the analysis stages.

Number 10 of Top 25 Best Kali Linux Penetration Testing Tools is Impacket Scripts . Following penetration testing tool, that contains python classes for network testing. Written in Python, this pool is useful in constructing network protocols and comes with multiple tools to perform remote service execution. It has an object-oriented API that provides seamless working with deep protocol hierarchies. Besides protocols, the library contains multiple tools such as Kerberos, Remote Execution, Server Tools/MiTM attacks, SMB/MSRPC, MSSQL / TDS, and more.

Everything starts with a goal. In this chapter, we will discuss the importance of goal-based penetration testing with a set of objectives and discuss misconceptions and how a typical vulnerability scan, penetration testing, and red teaming exercise can fail without the importance of a goal. This chapter also provides an overview of security testing and setting up a verification lab and focuses on customizing Kali to support some advanced aspects of penetration testing. By the end of this chapter, you'll have learned the following:

Every household, individual and public and private business in the world has something to worry about in cyber space, such as privacy, data loss, malware, cyber terrorism, and identity theft. Everything starts with a concept of protection; if you ask the question "What is security testing?" to 100 different security consultants, it is very likely that you'll hear different responses. In the simplest form, security testing is a process to determine that any information asset or system is protected and its functionality is maintained as intended.

While objective-based penetration testing is time-based, depending on the specific problem that an organization faces, an example of an objective is: We are most worried about the online portal and fraud transactions. So, the objective now is to compromise the portal or administrators through phishing or take over the approval chains through a system flaw. Every objective comes with its own tactics, techniques, and procedures that will support the primary goal of the penetration test activity. We will be exploring all of the different ways throughout this book using Kali Linux.

Raspberry Pis are single board devices that are compact in nature and can run just like a fully loaded computer with minimal functionalities. These devices are extremely useful during RTE and penetration testing activities. The base of the operating system is loaded from a SD card just like a hard disk drive for normal computers/laptops.

After the Docker installation, it should be fairly simple to run Kali Linux by running the docker pull kalilinux/kali-linux-docker and docker run -t -i kalilinux/kali-linux-docker /bin/bashcommands to confirm installation.

Once the Docker download is complete, you can run the Docker image by running docker run -t -i kalilinux/kali-linux-docker /bin/bash. You should be able to see what's shown in the following screenshot:

Robert Beggs is the founder and CEO of DigitalDefence, a Canadian-focused company that specializes in preventing and responding to information security incidents. Robert is a security practitioner with more than 15 years of experience. He has been responsible for the technical leadership and project management of more than 300 consulting engagements, including policy development and review, standards compliance, penetration testing of wired and wireless networks, third party security assessments, incident response and data forensics, and other consulting projects. Previously, he provided security services for a major Canadian financial institution and Netigy, a global network and security infrastructure firm based in San Jose.

Kali Linux has been developed to be tailored to the needs of professionals in this sector, and it is not recommended for those unfamiliar with Linux distribution. Therefore, prior knowledge of penetration testing is required to use this tool. The platform warns against using it without prior experience, as the misuse of security and penetration testing tools may cause significant damage. Additionally, before using Kali Linux, make sure you research hardware compatibility as it may not work with some hardware. It is recommended to install Kali Linux first in Virtual Machine and then install it on your own hardware. 


Advanced Penetration Testing: Hacking the World's Most Secure Networks takes hacking far beyond Kali linux and Metasploit to provide a more complex attack simulation. Featuring techniques not taught in any certification prep or covered by common defensive scanners, this book integrates social engineering, programming, and vulnerability exploits into a multidisciplinary approach for targeting and compromising high security environments. From discovering and creating attack vectors, and moving unseen through a target enterprise, to establishing command and exfiltrating data--even from organizations without a direct Internet connection--this guide contains the crucial techniques that provide a more accurate picture of your system's defense. Custom coding examples use VBA, Windows Scripting Host, C, Java, JavaScript, Flash, and more, with coverage of standard library applications and the use of scanning tools to bypass common defensive measures.

Typical penetration testing consists of low-level hackers attacking a system with a list of known vulnerabilities, and defenders preventing those hacks using an equally well-known list of defensive scans. The professional hackers and nation states on the forefront of today's threats operate at a much more complex level--and this book shows you how to defend your high security network.

Today's threats are organized, professionally-run, and very much for-profit. Financial institutions, health care organizations, law enforcement, government agencies, and other high-value targets need to harden their IT infrastructure and human capital against targeted advanced attacks from motivated professionals. Advanced Penetration Testing goes beyond Kali linux and Metasploit and to provide you advanced pen testing for high security networks. e24fc04721

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