Book Image

Metasploit Penetration Testing Cookbook - Third Edition

By : Daniel Teixeira, Abhinav Singh, Nipun Jaswal, Monika Agarwal
Book Image

Metasploit Penetration Testing Cookbook - Third Edition

By: Daniel Teixeira, Abhinav Singh, Nipun Jaswal, Monika Agarwal

Overview of this book

Metasploit is the world's leading penetration testing tool and helps security and IT professionals find, exploit, and validate vulnerabilities. Metasploit allows penetration testing automation, password auditing, web application scanning, social engineering, post exploitation, evidence collection, and reporting. Metasploit's integration with InsightVM (or Nexpose), Nessus, OpenVas, and other vulnerability scanners provides a validation solution that simplifies vulnerability prioritization and remediation reporting. Teams can collaborate in Metasploit and present their findings in consolidated reports. In this book, you will go through great recipes that will allow you to start using Metasploit effectively. With an ever increasing level of complexity, and covering everything from the fundamentals to more advanced features in Metasploit, this book is not just for beginners but also for professionals keen to master this awesome tool. You will begin by building your lab environment, setting up Metasploit, and learning how to perform intelligence gathering, threat modeling, vulnerability analysis, exploitation, and post exploitation—all inside Metasploit. You will learn how to create and customize payloads to evade anti-virus software and bypass an organization's defenses, exploit server vulnerabilities, attack client systems, compromise mobile phones, automate post exploitation, install backdoors, run keyloggers, highjack webcams, port public exploits to the framework, create your own modules, and much more.

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Metasploit Penetration Testing Cookbook - Third Edition
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Feb, 2018 | 426 pages
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Table of Contents (20 chapters)
Title Page
Title Page
Copyright and Credits
Copyright and Credits
Contributors
Contributors
Packt Upsell
Packt Upsell
Preface
Preface
Free Chapter
1
Metasploit Quick Tips for Security Professionals
Metasploit Quick Tips for Security Professionals
Introduction
Installing Metasploit on Windows
Installing Linux and macOS
Installing Metasploit on macOS
Using Metasploit in Kali Linux
Setting up a penetration-testing lab
Setting up SSH connectivity
Connecting to Kali using SSH
Configuring PostgreSQL
Creating  workspaces
Using the database
Using the hosts command
Understanding the services command
2
Information Gathering and Scanning
Information Gathering and Scanning
Introduction
Passive information gathering with Metasploit
Active information gathering with Metasploit
Port scanning—the Nmap way
Port scanning—the db_nmap way
Host discovery with ARP Sweep
UDP Service Sweeper
SMB scanning and enumeration
Detecting SSH versions with the SSH Version Scanner
FTP scanning
SMTP enumeration
SNMP enumeration
HTTP scanning
WinRM scanning and brute forcing
Integrating with Nessus
Integrating with NeXpose
Integrating with OpenVAS
3
Server-Side Exploitation
Server-Side Exploitation
Introduction
Exploiting a Linux server
SQL injection
Types of shell
Exploiting a Windows Server machine
Exploiting common services
MS17-010 EternalBlue SMB Remote Windows Kernel Pool Corruption
MS17-010 EternalRomance/EternalSynergy/EternalChampion
Installing backdoors
Denial of Service
4
Meterpreter
Meterpreter
Introduction
Understanding the Meterpreter core commands
Understanding the Meterpreter filesystem commands
Understanding Meterpreter networking commands
Understanding the Meterpreter system commands
Setting up multiple communication channels with the target
Meterpreter anti-forensics
The getdesktop and keystroke sniffing
Using a scraper Meterpreter script
Scraping the system using winenum
Automation with AutoRunScript
Meterpreter resource scripts
Meterpreter timeout control
Meterpreter sleep control
Meterpreter transports
Interacting with the registry
Loading framework plugins
Meterpreter API and mixins
Railgun—converting Ruby into a weapon
Adding DLL and function definitions to Railgun
Injecting the VNC server remotely
Enabling Remote Desktop
5
Post-Exploitation
Post-Exploitation
Introduction
Post-exploitation modules
Bypassing UAC
Dumping the contents of the SAM database
Passing the hash
Incognito attacks with Meterpreter
Using Mimikatz
Setting up a persistence with backdoors
Becoming TrustedInstaller
Backdooring Windows binaries
Pivoting with Meterpreter
Port forwarding with Meterpreter
Credential harvesting
Enumeration modules
Autoroute and socks proxy server
Analyzing an existing post-exploitation module
Writing a post-exploitation module
6
Using MSFvenom
Using MSFvenom
Introduction
Payloads and payload options
Encoders
Output formats
Templates
Meterpreter payloads with trusted certificates
7
Client-Side Exploitation and Antivirus Bypass
Client-Side Exploitation and Antivirus Bypass
Introduction
Exploiting a Windows 10 machine
Bypassing antivirus and IDS/IPS
Metasploit macro exploits
Human Interface Device attacks
HTA attack
Backdooring executables using a MITM attack
Creating a Linux trojan
Creating an Android backdoor
8
Social-Engineer Toolkit
Social-Engineer Toolkit
Introduction
Getting started with the Social-Engineer Toolkit
Working with the spear-phishing attack vector
Website attack vectors
Working with the multi-attack web method
Infectious media generator
9
Working with Modules for Penetration Testing
Working with Modules for Penetration Testing
Introduction
Working with auxiliary modules
DoS attack modules
Post-exploitation modules
Understanding the basics of module building
Analyzing an existing module
Building your own post-exploitation module
Building your own auxiliary module
10
Exploring Exploits
Exploring Exploits
Introduction
Common exploit mixins
Exploiting the module structure
Using MSFvenom to generate shellcode
Converting an exploit to a Metasploit module
Porting and testing the new exploit module
Fuzzing with Metasploit
Writing a simple fuzzer
11
Wireless Network Penetration Testing
Wireless Network Penetration Testing
Introduction
Metasploit and wireless
Understanding an evil twin attack
Configuring Karmetasploit
Wireless MITM attacks
SMB relay attacks
12
Cloud Penetration Testing
Cloud Penetration Testing
Introduction
Metasploit in the cloud
Metasploit PHP Hop
Phishing from the cloud
Setting up a cloud penetration testing lab
13
Best Practices
Best Practices
Introduction
Best practices
Using Metasploit over the Tor network
Metasploit logging
Documentation
Cleaning up
Other Books You May Enjoy
Other Books You May Enjoy
Leave a review - let other readers know what you think
Index
Index

Introduction

Metasploit is currently the world's leading penetration-testing tool, and one of the biggest open-source projects in information security and penetration testing. It has totally revolutionized the way we can perform security tests on our systems. The reason Metasploit is so popular is the wide range of tasks that it can perform to ease the work of penetration testing to make systems more secure. Metasploit is available for all popular operating systems. The working process of the framework is almost the same for all of them. In this book, we will primarily work on Kali Linux as it comes with the preinstalled Metasploit Framework and other third-party tools which run over the framework.

Let's proceed with a quick introduction to the framework and the various terminologies related to it:

  • Metasploit Framework: This is a free, open-source penetration-testing framework started by H. D. Moore in 2003, which was later acquired by Rapid7. The current stable versions of the framework are written using the Ruby language. It has the world's largest database of tested exploits and receives more than a million downloads every year. It is also one of the most complex projects built in Ruby to date.
  • Vulnerability: This is a weakness which allows an attacker/pentester to break into or compromise a system's security. This weakness can exist in the operating system, the application software, or even in the network protocols.
  • Exploit: An exploit is a piece of code which allows an attacker/tester to take advantage of the vulnerable system and compromise its security. Every vulnerability has its own corresponding exploit. Metasploit has more than 1,700 exploits.
  • Payload: This is the actual code which does the work. It runs on the system after exploitation. It is mostly used to set up a connection between the attacking and victim machines. Metasploit has more than 500 payloads.
  • Module: Modules are the small building blocks of a complete system. Every module performs a specific task and a complete system is built by combining several modules to function as a single unit. The biggest advantage of such an architecture is that it becomes easy for developers to integrate new exploit code and tools into the framework.

The Metasploit Framework has a modular architecture and the exploits, payload, encoders, and so on are considered to be separate modules:

Let's examine the architecture diagram closely.

Metasploit uses different libraries that hold the key to the proper functioning of the framework. These libraries are a collection of predefined tasks, operations, and functions that can be utilized by different modules of the framework. The most fundamental part of the framework is the Ruby extension (Rex) library. Some of the components provided by Rex include a wrapper socket subsystem, implementations of protocol clients and servers, a logging subsystem, exploitation utility classes, and a number of other useful classes. Rex itself is designed to have no dependencies, other than what comes with the default Ruby installation.

Then we have the MSF Core library that extends Rex. Core is responsible for implementing all of the required interfaces that allow for interacting with exploit modules, sessions, and plugins. This core library is extended by the framework base library, which is designed to provide simpler wrapper routines for dealing with the framework core, as well as providing utility classes for dealing with different aspects of the framework, such as serializing a module state to different output formats. Finally, the base library is extended by the framework's user interface (UI) that implements support for the different types of UIs to the framework itself, such as the command console and the web interface.

There are two different UIs provided with the framework, namely msfconsole and a web interface. Checking out bought interfaces is highly recommended but, in this book, we will primarily work on the msfconsole interface. This is because msfconsole provides the best support to the framework, leveraging all of the functionalities.

The msfconsole interface is by far the most talked-about part of the Metasploit Framework, and for good reason, as it is one of the most flexible, character-rich, and well-supported tools within the framework. It actually provides a handy all-in-one interface for every choice and setting attainable in the framework; it's like a one-stop shop for all of your pen-testing dreams. We can use msfconsole to do anything, including launching an exploit, loading an auxiliary, executing enumeration, producing listeners, or executing mass exploitations in contrast to an entire network.

A web interface is available for you to work with Metasploit Community, Express, and Pro. To launch the web interface, open a web browser and go to https://localhost:3790.

Note

To see the operating systems that are currently supported and the minimum system requirements, please visit https://www.rapid7.com/products/metasploit/system-requirements.

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