Wireshark for Security Professionals

Using Wireshark and the Metasploit Framework

Jessey Bullock, Jeff T. Parker

• Publisher: Wiley
• Year: 2017
• Print ISBN: 9781118918210
• eBook ISBN: 9781118918227
• Edition: 1
• Topic: Computer Science
• Subtopic: Cryptography
• Index: Computer Science

Master Wireshark to solve real-world security problems

If you don't already use Wireshark for a wide range of information security tasks, you will after this book. Mature and powerful, Wireshark is commonly used to find root cause of challenging network issues. This book extends that power to information security professionals, complete with a downloadable, virtual lab environment.

Wireshark for Security Professionals covers both offensive and defensive concepts that can be applied to essentially any InfoSec role. Whether into network security, malware analysis, intrusion detection, or penetration testing, this book demonstrates Wireshark through relevant and useful examples.

Master Wireshark through both lab scenarios and exercises. Early in the book, a virtual lab environment is provided for the purpose of getting hands-on experience with Wireshark. Wireshark is combined with two popular platforms: Kali, the security-focused Linux distribution, and the Metasploit Framework, the open-source framework for security testing. Lab-based virtual systems generate network traffic for analysis, investigation and demonstration. In addition to following along with the labs you will be challenged with end-of-chapter exercises to expand on covered material.

Lastly, this book explores Wireshark with Lua, the light-weight programming language. Lua allows you to extend and customize Wireshark's features for your needs as a security professional. Lua source code is available both in the book and online. Lua code and lab source code are available online through GitHub, which the book also introduces. The book's final two chapters greatly draw on Lua and TShark, the command-line interface of Wireshark.

By the end of the book you will gain the following:

• Master the basics of Wireshark
• Explore the virtual w4sp-lab environment that mimics a real-world network
• Gain experience using the Debian-based Kali OS among other systems
• Understand the technical details behind network attacks
• Execute exploitation and grasp offensive and defensive activities, exploring them through Wireshark
• Employ Lua to extend Wireshark features and create useful scripts

To sum up, the book content, labs and online material, coupled with many referenced sources of PCAP traces, together present a dynamic and robust manual for information security professionals seeking to leverage Wireshark.

Chapter 1
Introducing Wireshark

Welcome to Wireshark for Security Professionals. This introductory chapter covers three broad topics. In the first part, we discuss what Wireshark is used for and when to use it.

The second part of this chapter introduces the popular graphic user interface (GUI). The GUI for Wireshark can appear quite busy at first, so we immediately want to get familiar with its layout. We break down the different areas of the interface, how they relate to one another, and the reasoning for needing each one. We also discuss how and when each part of the interface helps you maximize your use of Wireshark.

In the third part of this chapter, we discuss the way Wireshark filters data presented on the interface. Being familiar with Wireshark's interface helps you appreciate all the data presented, but the amount of data can still be overpowering. Wireshark offers ways to filter or separate what you need from all that is presented. The last part is about different types of filters and how you can customize these filters.

Wireshark can appear to be a complicated tool, but by the end of this first chapter, the hope is you have a much higher comfort level with the tool's purpose, interface, and ability to present you with what you want to see.

What Is Wireshark?

Wireshark, in its most basic sense, is a tool to understand data you capture from a network. The captured data is interpreted and presented in individual packet form for analysis, all within Wireshark. As you probably already know, packets are the chunks of data streaming on a network. (Technically, depending on the context level of where in the system the data is interpreted, chunks are called frames, datagrams, packets, or segments, but we'll just use “packets” for now.) Wireshark is a network and protocol analyzer tool, free for download and use on a variety of platforms, spanning many flavors of Unix and Windows.

Wireshark first captures the data from a network interface and then breaks the capture into the frames, segments, and packets, understanding where they begin and end. Wireshark then interprets and presents this data in the context of addressing, protocols and data. You can analyze the captures immediately or save them to load later and share with others. In order for Wireshark to view and capture all packets, not just those involving the capturing system, the network interface is placed in promiscuous mode (also called monitor mode) in the context of capturing on a wireless network. Finally, what grants you the ability to analyze packets in Wireshark are the dissectors. All these basic elements are discussed in more detail in Chapter 4, in the context of “sniffing” or capturing data, and how that captured data is interpreted.

A Best Time to Use Wireshark?

Wireshark is an immensely powerful tool with quite a bit of deep and complex functionality. It is capable of handling a wide range of known (and unknown) protocols. But although the functionality range is broad, most of it aligns to one end: to capture packets and analyze them. Being able to take the bits and bytes and present them in an organized, familiar, and human-readable format is what brings people to think of using Wireshark.

Before launching Wireshark, it's important to understand when to use it and when not to use it. Sure, it's a great tool, but like any tool, it's best used when it's the right tool for the job.

Here are scenarios when it's ideal to use Wireshark:

• To look for the root cause of a known problem
• To search for a certain protocol or stream between devices
• To analyze specific timing, protocol flags, or bits on the wire

And while not ideal, Wireshark can also be used:

• To discover which devices or protocols are the top talkers
• To see a rough picture of network traffic
• To follow a conversation between two devices

You get the idea. Wireshark is ideal for determining a root cause of an understood problem. While not ideal for browsing network traffic or making high-level judgments about the network, Wireshark does have some features to show those statistics. But Wireshark can't and shouldn't be the first tool thought of early on in discovering a problem. Someone who opens Wireshark to skim through the list of packets to assess network health would soon be overwhelmed. Instead, Wireshark is for problem solvers, for the detectives who already know their suspects well.

Avoiding Being Overwhelmed

The majority of people who walk away from Wireshark do so because they find it overwhelming after only a few early experiences. To label Wireshark as overwhelming is misleading, however. What really paralyzes new users is the traffic, the list of packets flying by, not the application's functionality. And, fair enough, once you start a capture and the packets scroll by in real time, it's definitely intimidating. (But that's what filters are for!)

To avoid being overwhelmed, consider two aspects of Wireshark before diving into it:

• The interface—how it's laid out and why
• Filters—how they work to reveal what you want

Once you get a quick appreciation of the tool's interface and how to write a filter, Wireshark suddenly appears intuitive and shows its power, without the scare factor. And that's what we focus on for the rest of this chapter.

The following sections are on the most important aspects that you need immediately to be comfortable using Wireshark. If you are already familiar with Wireshark, as well as filters, feel free to skim this chapter as a refresher so that you can be sure you are...

Table of contents

• Cover
• Title Page
• Table of Contents
• Introduction
• Chapter 1: Introducing Wireshark
• Chapter 2: Setting Up the Lab
• Chapter 3: The Fundamentals
• Chapter 4: Capturing Packets
• Chapter 5: Diagnosing Attacks
• Chapter 6: Offensive Wireshark
• Chapter 7: Decrypting TLS, Capturing USB, Keyloggers, and Network Graphing
• Chapter 8: Scripting with Lua
• End User License Agreement