Jailbreaking is used by the forensic community to access the file system of iOS devices, perform physical extraction and decrypt device secrets. Jailbreaking the device is one of the most straightforward ways to gain low-level access to many types of evidence not available with any other extraction methods.

On the negative side, jailbreaking is a process that carries risks and other implications. Depending on various factors such as the jailbreak tool, installation method and the ability to understand and follow the procedure will affect the risks and consequences of installing a jailbreak. In this article we’ll talk about the risks and consequences of using various jailbreak tools and installation methods.

Why jailbreak?

Why jailbreak, and should you jailbreak at all? Speaking of mobile forensics, jailbreaking the device helps extract some additional bits and pieces of information compared to other acquisition methods. Before discussing the differences between the different acquisition methods, let’s quickly look at what extraction methods are available for iOS devices.

Logical acquisition

Logical acquisition is the simplest, cleanest and the most straightforward acquisition method by a long stretch. During logical acquisition, experts can make the iPhone (iPad, iPad Touch) backup its contents. In addition to the backup (and regardless of whether or not the user protected backups with a password), logical acquisition enables experts to extract media files (pictures and videos), crash logs and shared files. Logical acquisition, when performed properly, yields a comprehensive set of data including (for password-protected backups) the content of the user’s keychain.

Requirements: the iOS device must be working and not in USB Restricted mode; you must be able to connect it to the computer and perform the pairing procedure (during this step, iOS 11 and 12 will require the passcode). Alternatively, one can use an existing pairing record extracted from the user’s computer.

A backup extracted during the course of logical acquisition may come out encrypted. If this is the case, experts may be able to reset the backup password, an action that carries consequences on its own (more information in Step by Step Guide to iOS Jailbreaking and Physical Acquisition, look up the “If you have to reset the backup password” chapter). Jailbreaking the device is a viable alternative to resetting the backup password. After you jailbreak, you’ll be able to extract all of the same information as available in the backup, and more. In addition, you’ll be able to view the user’s backup password in plain text (refer to “Extracting the backup password from the keychain” in the same article).

Over-the-air (iCloud) extraction

Remote extraction of device data may be possible if you know the user’s Apple ID and password and have access to their second authentication factor (if two-factor authentication is enabled on the user’s Apple account). Some bits and pieces may be accessed without the password by utilizing a binary authentication token. This, however, has very limited use today.

Requirements: you must know the user’s Apple ID login and password and have access to the second authentication factor (if 2FA is enabled on the user account). If you require access to protected data categories (iCloud Keychain, iCloud Messages, Health etc.), you must know the passcode or system password to one of the already enrolled devices. To access synchronized data, you may use an existing authentication token instead of the login/password/2FA sequence.

During the course of iCloud extraction, you’ll have access to some or all of the following: iCloud backups, synchronized data and media files. If you know the passcode to the user’s device, you may be able to access their iCloud Keychain, Health and Messages data.

Apple constantly improves iCloud protection, making it difficult or even impossible to access some types of data in a way other than restoring an actual iOS device. In a game of cat and mouse, manufacturers of forensic software try overcoming such protection measures, while Apple tries to stop third-party tools from accessing iCloud data.

Note that some iCloud data (the backups, media files and synchronized data) can be obtained from Apple with a court order. However, even if you have authority to file a request, Apple will not provide any encrypted data such as the user’s passwords (iCloud Keychain), Health and Messages.

Physical acquisition

Physical is the most in-depth extraction method available. Today, physical acquisition of iOS devices is limited to file system extraction as opposed to imaging and decrypting the entire partition. With this method, experts can image the file system, access sandboxed app data, decrypt the all keychain records including those with this_device_only attribute, extract system logs, and more.

Compared to other acquisition methods, physical extraction additionally offers access to all of the following:

File system extraction:

• App databases with uncommitted transactions and WAL files
• Sandboxed app data for those apps that don’t back up their contents
• Access to secure chats and protected messages (e.g. Signal, Telegram and many others)
• Downloaded email messages
• System logs

Keychain:

• Items protected with this_device_only attribute
• This includes the password to iTunes backups

Physical is the riskiest and the most demanding method as well. The list of requirements includes the device itself in the unlocked state; the ability to pair the device with the computer; and a version of iOS that has known vulnerabilities so that a jailbreak can be installed.

The risks of jailbreaking

The risks of jailbreaking iOS devices largely depend on the jailbreak tool and installation procedure. However, the main risk of today’s jailbreaks is not about bricking the device. A real risk of making the device unbootable existed in jailbreaks developed for early versions of iOS (up to and including iOS 9). These old jailbreaks were patching the kernel and attempted to bypass the system’s Kernel Patch Protection (KPP) by patching other parts of the operating system. This was never completely reliable; worst case scenario the device would not boot at all.

Modern jailbreaks (targeting iOS 10 and newer) are not modifying the kernel and do not need to deal with Kernel Patch Protection. As a result, the jailbroken device will always boot in a non-jailbroken state; you’ll have to reapply the jailbreak on every boot.

The two risks of today’s jailbreaks are:

1. Exposing the device to the Internet. By allowing the device going online while installing a jailbreak, you’re effectively allowing the device to sync data, downloading information that was not there at the time the device was seized. Even worse, you’ll make the device susceptible to any remote block or remote erase commands that could be pending.The procedure of installing a jailbreak for the purpose of physical extraction is vastly different from jailbreaking for research or other purposes. In particular, forensic experts are struggling to keep devices offline in order to prevent data leaks, unwanted synchronization and issues with remote device management that may remotely block or erase the device. While there is no lack of jailbreaking guides and manuals for “general” jailbreaking, installing a jailbreak for the purpose of physical acquisition has multiple forensic implications and some important precautions.Mitigation: you can mitigate this risk by following the correct jailbreak installation procedure laid out in our guide on iOS jailbreaking.
2. Jailbreak failing to install. Jailbreaks exploit chains of vulnerabilities in the operating system in order to obtain superuser privileges, escape the sandbox and allow the execution of unsigned applications. Since multiple vulnerabilities are consecutively exploited, the jailbreaking process may fail at any time.
   Mitigation: since different jailbreaks are using different code and may even target different exploits, the different jailbreak tools have different success rates. Do try another jailbreak tool if your original tool of choice had failed.

Consequences of jailbreaking

Different jailbreaks bear different consequences. A classic jailbreak such as Meridian, Pangu, TaiG, Chimera or Unc0ver needs to perform a long list of things in order to comply with what is expected of a jailbreak. Since the intended purpose of a jailbreak is allowing to install unsigned apps from third-party repositories, jailbreaks need to disable code signing checks and install a third-party package manager such as Cydia or Sileo. Such things require invasive modifications of the core of the operating system, inevitably remounting and modifying the system partition and writing files to the data partition.

The new generation of jailbreaks has recently emerged. Rootless jailbreaks (e.g. RootlessJB) do not, by design, modify the system partition. A rootless jailbreak has a much smaller footprint compared to any classic jailbreak. On the flip side, rootless jailbreaks will not easily allow executing unsigned code or install a third-party package manager. However, they do include a working SSH daemon, making it possible to perform file system extraction.

Since rootless jailbreaks do not alter the content of the system partition, one can easily remove such jailbreaks from the device, return the system to pre-jailbroken state and receive OTA updates afterwards. Generally speaking, this task would be very difficult (and sometimes impossible) to achieve when using classic jailbreaks.

We have an article in our blog with more information about rootless jailbreaks and their differences from classic jailbreaks: iOS 12 Rootless Jailbreak.

Companies such as Cellebrite and GrayShift do not rely on public jailbreaks to perform the extraction. Instead, they use a set of undisclosed exploits to access the file system of iOS devices directly. Using exploits directly has a number of benefits as the device’s file system is usually untouched during the extraction. The only traces left on the device after using an exploit for file system extraction would be entries in various system logs.

So let us compare consequences of using a classic or rootless jailbreak to extract the file system.

File system remount

Generally speaking, we’d like to avoid the remount of the file system when jailbreaking the device. While remounting the file system opens read/write access to the root of the file system, it also introduces the potential of bricking the device due to incompatible modifications of the system partition that are made possible with r/w access. We can still extract user data and decrypt the keychain without remounting the file system.

Modified system partition

This, again, is something that we’d like to avoid when performing forensic extractions. Any modification made to the system partition can potentially brick the device or make it less stable. A modified system partition may break OTA updates (a full update or restore through iTunes is still possible). Classic jailbreaks write files to the system partition to ensure that unsigned apps can be installed and launched. We can still access the full content of the data partition and decrypt the keychain without modifying the system partition.

Modified boot image

Early jailbreaks (up to and including jailbreaks targeting all versions of iOS 9) used to patch the kernel in order to achieve untethered jailbreak. While being “untethered” means the device remains jailbroken indefinitely between reboots, modifying the kernel has some severe disadvantages including compromised stability and general unreliability of jailbroken devices. Since Apple introduced advanced Kernel Patch Protection (KPP) mechanisms, patching the kernel became less attractive. Public jailbreaks targeting iOS 10 and all newer versions of iOS got away from patching the kernel.

System log entries

The installation and operation of a jailbreak leaves multiple traces in the form of entries in various log files throughout the system. This is pretty much unavoidable and should be taken into consideration.

OTA compatibility

Depending on the type of a jailbreak, a jailbroken device may or may not be able to accept over-the-air (OTA) updates after you’re done with extraction. Some classic jailbreaks make modifications to the device that make it impossible to install OTA updates even after the jailbreak is removed. Some jailbreaks make it possible to create a system restore point (using APFS mechanisms), so at least in theory rolling back the device to pre-jailbroken state should be possible. In our experience, this is not reliable enough. On the other hand, rootless jailbreaks to not alter the system partition at all, making OTA updates easily possible.

Access to the root of the file system “/”

Classic jailbreaks provide read/write access to the root of the file system, making it possible to dump the content of the system partition as well as the data partition. Rootless jailbreaks only offer access to the content of the data partition (“/var”), which is sufficient for the purpose of forensic extraction.

Access to the data partition “/var”

All types of jailbreaks offer access to user data stored in the data partition. The complete file system is available including installed applications and their sandboxed data, databases, system log files and much more.

Access to keychain

One can decrypt the keychain (passwords and autofill entries in Safari and installed apps) using either type of jailbreak. All keychain entries can be decrypted including those protected with the highest protection class and flagged this_device_only.

Repeatable results

Jailbreaks are unreliable in their nature. They are using undocumented exploits to obtain superuser privileges and secure access to the file system. A jailbreak may fail to install and require multiple attempts. Since jailbreaks modify the content of the device, we may not consider the results to be fully repeatable. However, rootless jailbreaks feature significantly cleaner footprint compared to classic ones.

Conclusion

Without a doubt, jailbreaks do have a fair share of forensic implications. One can significantly reduce the number and severity of negative consequences by selecting and using the jailbreak with care. However, even in worst-case scenarios, the benefits of physical extraction may far outweigh the drawbacks of jailbreaking.