Mastering Metasploit,

Take your penetration testing and IT security skills to a whole new level with the secrets of Metasploit, 3rd Edition

Nipun Jaswal

• Publisher: Packt Publishing
• Year: 2018
• ISBN:
  9781788994200
• Edition: 3
• Topic: Computer Science
• Subtopic: Cyber Security
• Index: Computer Science

Discover the next level of network defense with the Metasploit framework

Key Features

• Gain the skills to carry out penetration testing in complex and highly-secured environments
• Become a master using the Metasploit framework, develop exploits, and generate modules for a variety of real-world scenarios
• Get this completely updated edition with new useful methods and techniques to make your network robust and resilient

Book Description

We start by reminding you about the basic functionalities of Metasploit and its use in the most traditional ways. You'll get to know about the basics of programming Metasploit modules as a refresher and then dive into carrying out exploitation as well building and porting exploits of various kinds in Metasploit.

In the next section, you'll develop the ability to perform testing on various services such as databases, Cloud environment, IoT, mobile, tablets, and similar more services. After this training, we jump into real-world sophisticated scenarios where performing penetration tests are a challenge. With real-life case studies, we take you on a journey through client-side attacks using Metasploit and various scripts built on the Metasploit framework.

By the end of the book, you will be trained specifically on time-saving techniques using Metasploit.

What you will learn

• Develop advanced and sophisticated auxiliary modules
• Port exploits from PERL, Python, and many more programming languages
• Test services such as databases, SCADA, and many more
• Attack the client side with highly advanced techniques
• Test mobile and tablet devices with Metasploit
• Bypass modern protections such as an AntiVirus and IDS with Metasploit
• Simulate attacks on web servers and systems with Armitage GUI
• Script attacks in Armitage using CORTANA scripting

Who this book is for

This book is a hands-on guide to penetration testing using Metasploit and covers its complete development. It shows a number of techniques and methodologies that will help you master the Metasploit framework and explore approaches to carrying out advanced penetration testing in highly secured environments.

Approaching a Penetration Test Using Metasploit

Penetration testing is an intentional attack on a computer-based system where the intention is to find vulnerabilities, security weaknesses, and certifying whether a system is secure. A penetration test will advise an organization on their security posture if it is vulnerable to an attack, whether the implemented security is enough to oppose any invasion, which security controls can be bypassed, and much more. Hence, a penetration test focuses on improving the security posture of an organization.

Achieving success in a penetration test largely depends on using the right set of tools and techniques. A penetration tester must choose the right set of tools and methodologies to complete a test. While talking about the best tools for penetration testing, the first one that comes to mind is Metasploit. It is considered one of the most effective auditing tools to carry out penetration testing today. Metasploit offers a wide variety of exploits, an excellent exploit development environment, information gathering and web testing capabilities, and much more.

This book has been written so that it will not only cover the frontend perspectives of Metasploit, but it will also focus on the development and customization of the framework as well. This book assumes that the reader has basic knowledge of the Metasploit framework. However, some of the sections of this book will help you recall the basics as well.

While covering Metasploit from the very basics to the elite level, we will stick to a step-by-step approach, as shown in the following diagram:

This chapter will help you recall the basics of penetration testing and Metasploit, which will help you warm up to the pace of this book.

In this chapter, you will learn about the following topics:

• The phases of penetration testing
• The basics of the Metasploit framework
• The workings of Metasploit exploit and scanner modules
• Testing a target network with Metasploit
• The benefits of using databases
• Pivoting and diving deep into internal networks

An important point to take note of here is that we might not become an expert penetration tester in a single day. It takes practice, familiarization with the work environment, the ability to perform in critical situations, and most importantly, an understanding of how we have to cycle through the various stages of a penetration test.

When we think about conducting a penetration test on an organization, we need to make sure that everything is set correctly and is according to a penetration test standard. Therefore, if you feel you are new to penetration testing standards or uncomfortable with the term Penetration Testing Execution Standard (PTES), please refer to http://www.pentest-standard.org/index.php/PTES_Technical_Guidelines to become more familiar with penetration testing and vulnerability assessments. According to PTES, the following diagram explains the various phases of a penetration test:

Refer to the pentest standard website, http://www.pentest-standard.org/index.php/Main_Page to set up the hardware and systematic stages to be followed in setting up a work environment.

Organizing a penetration test

Before we start firing sophisticated and complex attacks with Metasploit, let's understand the various phases of a penetration test and see how to organize a penetration test on a professional scale.

Preinteractions

The very first phase of a penetration test, preinteractions, involves a discussion of the critical factors regarding the conduct of a penetration test on a client's organization, company, institute, or network with the client itself. This phase serves as the connecting line between the penetration tester, the client, and his/her requirements. Preinteractions help a client get enough knowledge on what is to be performed over his or her network/domain or server.

Therefore, the tester will serve here as an educator to the client. The penetration tester also discusses the scope of the test, gathers knowledge on all the domains under the scope of the project, and any special requirements that will be needed while conducting the analysis. The requirements include special privileges, access to critical systems, network or system credentials, and much more. The expected positives of the project should also be the part of the discussion with the client in this phase. As a process, preinteractions discuss some of the following key points:

• Scope: This section reviews the scope of the project and estimates the size of the project. The scope also defines what to include for testing and what to exclude from the test. The tester also discusses IP ranges and domains under the scope and the type of test (black box or white box). In case of a white box test, the tester discusses the kind of access and required credentials as well; the tester also creates, gathers, and maintains questionnaires for administrators. The schedule and duration of the test, whether to include stress testing or not, and payment, are included in the scope. A general scope document provides answers to the following questions:
  • What are the target organization's most significant security concerns?
  • What specific hosts, network address ranges, or applications should be tested?
  • What specific hosts, network address ranges, or applications should explicitly NOT be tested?
  • Are there any third parties that own systems or networks that are in the scope, and which systems do they hold (written permission must have been obtained in advance by the target organization)?
  • Will the test be performed in a live production environment or a test environment?
  • Will the penetration test include the following testing techniques: ping sweep of network ranges, a port scan of target hosts, vulnerability scan of targets, penetration of targets, application-level manipulation, client-side Java/ActiveX reverse engineering, physical penetration attempts, social engineering?
  • Will the penetration test include internal network testing? If so, how will access be obtained?
  • Are client/end user systems included in the scope? If so, how ...