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Learning iOS Penetration Testing
Learning iOS Penetration Testing

Learning iOS Penetration Testing: Secure your iOS applications and uncover hidden vulnerabilities by conducting penetration tests

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Learning iOS Penetration Testing

Chapter 2. Setting up Lab for iOS App Pentesting

 

"If I had eight hours to chop down a tree, I'd spend six hours sharpening my axe."

 
 --Abraham Lincoln

We are now aware about the basics of iOS app development and iOS security concepts. Now, let's set up the battlefield for penetration testing of iOS applications.

In this chapter, we will look at the following topics:

  • Need for jailbreaking
  • Hardware and software requirements
  • Jailbreaking iDevice
  • Connecting with iDevice
  • Installing utilities on iDevice
  • Pentesting using iOS Simulator

Need for jailbreaking

As studied in the previous chapter, iOS itself has a lot of security features. Neither installing any app outside of App Store nor accessing its filesystem by default is allowed by iOS.

To conduct a security assessment of an iOS application, we will need to access the iDevice's filesystem and keychain data, hook debuggers to applications, and so on. It's not possible to perform iOS app pentesting with so many restrictions and this is the point where we need to jailbreak the iDevice in order to bypass security restrictions provided by iOS.

What is jailbreak?

Jailbreaking is the privilege escalation from mobile user to root user.

Jailbreaking is exploiting the iOS vulnerability and maintaining root access on the device by installing utilities on it. Finding a jailbreak is itself an in-depth topic and beyond the scope of this book. We will only learn how to jailbreak iDevices with the available jailbreaking utilities.

Jailbreaking allows us to do the following:

  • Access...

Jailbreaking iDevice

Jailbreaking iDevice is similar to installing a software. First, you need to check whether there is any jailbreak available for your iDevice that is running the specific version of iOS.

Note

Jailbreaking iDevice may void your iDevice warranty. Readers should perform the jailbreak at their own risk. Do not use a jailbroken device for production purposes.

So, let's follow the steps in order to jailbreak the iDevice:

  1. First, check for availability of jailbreak. Jailbreak Wizard contains details about the available jailbreak for different version of iOS. To find whether any jailbreak is available for your iDevice, you can use the website at http://www.jailbreak-me.info/. The following image is a screenshot of this website:
    Jailbreaking iDevice
  2. Once you find the available jailbreak, it will also provide the link to download the jailbreak utility. You need to download it as per your supporting Windows/Mac/Linux platform. The interface will remain almost the same, regardless of the platform. The...

Connecting with iDevice

In Chapter 1, Introducing iOS Application Security, we had studied that iOS is very similar to a Unix-based system. So, let's log in to the device and check it.

To log in to iDevice, you should have SSH running on iDevice so that you can connect to it using the SSH client. In Cydia, search for OpenSSH and install it, as shown in the following screenshot:

Connecting with iDevice

Then, connect your iDevice to Wi-Fi and check the IP address of your device, as follows:

Connecting with iDevice

Now, from your PC/Mac system, connect to this IP address over SSH using any SSH client. It will prompt you for a username and password. The default credentials for SSH connection with any iDevice are username as root and password being alpine.

Once you logged in, you will notice a similar filesystem as Unix under the root directory, as shown in the following screenshot:

Connecting with iDevice

The most important thing is to change your default password otherwise, anyone over Wi-Fi could connect to your device using the default credentials. Therefore...

Installing utilities on iDevice

To perform iOS app pentesting, we require many utilities. You may have to add the latest repositories in Cydia sources in order to install the mentioned utilities. You can simply search required repositories online and add them in sources. In this section, we will set up most required utilities.

Therefore, we will need to search these utilities on Cydia and then use options such as Install. We need to install the following utilities:

  • Erica Utilities: It's a collection of command-line utilities, such as plutil, appSearch, and so on.

    You can install Erica Utilities by performing the following step. Search for Erica Utilities in Cydia and then use the Install option, as shown in the following screenshot:

    Installing utilities on iDevice

    You can use same technique to install almost all the other utilities. You may have to update source list by referring to the Adding sources to Cydia section in order to install all the required utilities.

  • class-dump-z: In iOS app pentesting, it's important...

Installing apps on iDevice

You must be familiar with installing apps via iTunes. In this section, you will learn how to install third-party apps that are not available on App Store or Cydia and are provided with the code bundle of this book.

Note

You should install the Installipa and AppSync in order to install third-party applications.

Therefore, let's install third-party apps using the following steps:

  1. Transfer the app.ipa file to your iDevice. You can use the SFTP technique, as described in the Transferring files to iDevice section of this chapter.
  2. Use the Installipa utility to install the app. Here, we will install the iGoat.ipa application file:
    Installing apps on iDevice

    Note

    Download the iGoat app from supported files provided with this chapter.

    The installation process takes place as depicted in the following screenshot:

    Installing apps on iDevice
  3. Here is the iGoat app interface that you will see once the app gets installed successfully on the device:
    Installing apps on iDevice

You can find all the installed third-party applications under /var/mobile/Containers/Data...

Need for jailbreaking


As studied in the previous chapter, iOS itself has a lot of security features. Neither installing any app outside of App Store nor accessing its filesystem by default is allowed by iOS.

To conduct a security assessment of an iOS application, we will need to access the iDevice's filesystem and keychain data, hook debuggers to applications, and so on. It's not possible to perform iOS app pentesting with so many restrictions and this is the point where we need to jailbreak the iDevice in order to bypass security restrictions provided by iOS.

What is jailbreak?

Jailbreaking is the privilege escalation from mobile user to root user.

Jailbreaking is exploiting the iOS vulnerability and maintaining root access on the device by installing utilities on it. Finding a jailbreak is itself an in-depth topic and beyond the scope of this book. We will only learn how to jailbreak iDevices with the available jailbreaking utilities.

Jailbreaking allows us to do the following:

  • Access complete...

Jailbreaking iDevice


Jailbreaking iDevice is similar to installing a software. First, you need to check whether there is any jailbreak available for your iDevice that is running the specific version of iOS.

Note

Jailbreaking iDevice may void your iDevice warranty. Readers should perform the jailbreak at their own risk. Do not use a jailbroken device for production purposes.

So, let's follow the steps in order to jailbreak the iDevice:

  1. First, check for availability of jailbreak. Jailbreak Wizard contains details about the available jailbreak for different version of iOS. To find whether any jailbreak is available for your iDevice, you can use the website at http://www.jailbreak-me.info/. The following image is a screenshot of this website:

  2. Once you find the available jailbreak, it will also provide the link to download the jailbreak utility. You need to download it as per your supporting Windows/Mac/Linux platform. The interface will remain almost the same, regardless of the platform. The Pangu...

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Key benefits

  • Achieve your goal to secure iOS devices and applications with the help of this fast paced manual
  • Find vulnerabilities in your iOS applications and fix them with the help of this example-driven guide
  • Acquire the key skills that will easily help you to perform iOS exploitation and forensics with greater confidence and a stronger understanding

Description

iOS has become one of the most popular mobile operating systems with more than 1.4 million apps available in the iOS App Store. Some security weaknesses in any of these applications or on the system could mean that an attacker can get access to the device and retrieve sensitive information. This book will show you how to conduct a wide range of penetration tests on iOS devices to uncover vulnerabilities and strengthen the system from attacks. Learning iOS Penetration Testing discusses the common vulnerabilities and security-related shortcomings in an iOS application and operating system, and will teach you to conduct static and dynamic analysis of iOS applications. This practical guide will help you uncover vulnerabilities in iOS phones and applications. We begin with basics of iOS security and dig deep to learn about traffic analysis, code analysis, and various other techniques. Later, we discuss the various utilities, and the process of reversing and auditing.

Who is this book for?

This book is for IT security professionals who want to conduct security testing of applications. This book will give you exposure to diverse tools to perform penetration testing. This book will also appeal to iOS developers who would like to secure their applications, as well as security professionals. It is easy to follow for anyone without experience of iOS pentesting.

What you will learn

  • Understand the basics of iOS app development, deployment, security architecture, application signing, application sandboxing, and OWASP TOP 10 for mobile
  • Set up your lab for iOS app pentesting and identify sensitive information stored locally
  • Perform traffic analysis of iOS devices and catch sensitive data being leaked by side channels
  • Modify an application's behavior using runtime analysis
  • Analyze an application's binary for security protection
  • Acquire the knowledge required for exploiting iOS devices
  • Learn the basics of iOS forensics
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Table of Contents

10 Chapters
1. Introducing iOS Application Security Chevron down icon Chevron up icon
2. Setting up Lab for iOS App Pentesting Chevron down icon Chevron up icon
3. Identifying the Flaws in Local Storage Chevron down icon Chevron up icon
4. Traffic Analysis for iOS Application Chevron down icon Chevron up icon
5. Sealing up Side Channel Data Leakage Chevron down icon Chevron up icon
6. Analyzing iOS Binary Protections Chevron down icon Chevron up icon
7. The iOS App Dynamic Analysis Chevron down icon Chevron up icon
8. iOS Exploitation Chevron down icon Chevron up icon
9. Introducing iOS Forensics Chevron down icon Chevron up icon
Index Chevron down icon Chevron up icon

Customer reviews

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Vinod Tiwari Mar 15, 2016
Full star icon Full star icon Full star icon Full star icon Full star icon 5
The book is structured very well. Helps you to grasp overall iOS security architecture and testing concepts. I was doing iOS security testing from last 2 years, this book helped me learning a new approach to test iOS.
Amazon Verified review Amazon
smith May 26, 2017
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excellent book must read complete guide from beginner to bug hunter
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kaleemshaik Apr 13, 2016
Full star icon Full star icon Full star icon Full star icon Full star icon 5
An awesome book to learn iOS pentesting in better way. The author has comprehensive knowledge on iOS security. Covered all the OWASP Mobile Top 10 Scenarios. Explained all the scenarios with clear steps. This book will help to learn iOS pentesting in practical approach . The author has well written scenarios for run time manipulation.This book will deal many iOS pentesting tools which comes handy while doing iOS PTA must have book for iOS Pen testers.
Amazon Verified review Amazon
Kenneth R. Van Wyk Mar 01, 2016
Full star icon Full star icon Full star icon Full star icon Full star icon 5
Caveat: I was a technical reviewer of this book, but received no remuneration other than a single free copy.That said, I found the book to be technically excellent. If you need to test the security of an iOS application, I know of no more current technical text than this. You'll learn everything from the iOS security basics through manipulating the ObjectiveC runtime to trick a poorly designed app into misbehaving (with security consequences). Each chapter delves deeper and deeper into the security aspects of the insides of iOS apps, with ample screenshots and examples.This book is best read interactively, where you work hands-on through all the examples in the book as you read through it. You'll get the most out of it that way, without a doubt. If you put in that effort, though, you'll emerge with a deep understanding of iOS app security and its common pitfalls.
Amazon Verified review Amazon
Kindle Oct 13, 2020
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Very nice course, i will recommend this book to my frnds thank you swaroop. . . . . . .
Amazon Verified review Amazon
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