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iOS Testing Environment

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Apple Developer Program

A provisioning identity is a collection of public and private keys that are associated an Apple developer account. In order to sign apps you need to pay 99$/year to register in the Apple Developer Program to get your provisioning identity. Without this you won't be able to run applications from the source code in a physical device. Another option to do this is to use a jailbroken device.

Starting in Xcode 7.2 Apple has provided an option to create a free iOS development provisioning profile that allows to write and test your application on a real iPhone. Go to Xcode --> Preferences --> Accounts --> + (Add new Appli ID you your credentials) --> Click on the Apple ID created --> Manage Certificates --> + (Apple Development) --> Done
__Then, in order to run your application in your iPhone you need first to indicate the iPhone to trust the computer. Then, you can try to run the application in the mobile from Xcode, but and error will appear. So go to Settings --> General --> Profiles and Device Management --> Select the untrusted profile and click "Trust".

Note that applications signed by the same signing certificate can share resources on a secure manner, like keychain items.

The provisioning profiles are stored inside the phone in /Library/MobileDevice/ProvisioningProfiles

Simulator

{% hint style="info" %} Note that a simulator isn't the same as en emulator. The simulator just simulates the behaviour of the device and functions but don't actually use them. {% endhint %}

The iOS SDK simulator offers a higher-level simulation of an iOS device. Most importantly, emulator binaries are compiled to x86 code instead of ARM code. Apps compiled for a real device don't run, making the simulator useless for black box analysis and reverse engineering.

Simulator

The first thing you need to know is that performing a pentest inside a simulator will much more limited than doing it in a jailbroken device.

All the tools required to build and support an iOS app are only officially supported on Mac OS.
Apple's de facto tool for creating/debugging/instrumenting iOS applications is Xcode. It can be used to download other components such as simulators and different SDK versions required to build and test your app.
It's highly recommended to download Xcode from the official app store. Other versions may be carrying malware.

The simulator files can be found in /Users/<username>/Library/Developer/CoreSimulator/Devices

To open the simulator, run Xcode, then press in the Xcode tab --> Open Developer tools --> Simulator
__In the following image clicking in "iPod touch [...]" you can select other device to test in:

Applications in the Simulator

Inside /Users/<username>/Library/Developer/CoreSimulator/Devices you may find all the installed simulators. If you want to access the files of an application created inside one of the emulators it might be difficult to know in which one the app is installed. A quick way to find the correct UID is to execute the app in the simulator and execute:

xcrun simctl list | grep Booted
    iPhone 8 (BF5DA4F8-6BBE-4EA0-BA16-7E3AFD16C06C) (Booted)

Once you know the UID the apps installed within it can be found in /Users/<username>/Library/Developer/CoreSimulator/Devices/{UID}/data/Containers/Data/Application

However, surprisingly you won't find the application here. You need to access /Users/<username>/Library/Developer/Xcode/DerivedData/{Application}/Build/Products/Debug-iphonesimulator/

And in this folder you can find the package of the application.

Emulator

Corellium is the only publicly available iOS emulator. It is an enterprise SaaS solution with a per user license model and does not offer any trial license.

Jailbeaking

Apple strictly requires that the code running on the iPhone must be signed by a certificate issued by Apple. Jailbreaking is the process of actively circumventing such restrictions and other security controls put in places by the OS. Therefore, once the device is jailbroken, the integrity check which is responsible for checking apps being installed is patched so it is bypassed.

{% hint style="info" %} Unlike Android, you cannot switch to "Developer Mode" in iOS to run unsigned/untrusted code on the device. {% endhint %}

Root in Android Comparison

iOS jailbreaking is often compared to Android rooting, but the process is actually quite different. To explain the difference, we'll first review the concepts of "rooting" and "flashing" on Android.

  • Rooting: This typically involves installing the su binary on the system or replacing the whole system with a rooted custom ROM. Exploits aren't required to obtain root access as long as the bootloader is accessible.
  • Flashing custom ROMs: This allows you to replace the OS that's running on the device after you unlock the bootloader. The bootloader may require an exploit to unlock it.

On iOS devices, flashing a custom ROM is impossible because the iOS bootloader only allows Apple-signed images to be booted and flashed. This is why even official iOS images can't be installed if they aren't signed by Apple, and it makes iOS downgrades only possible for as long as the previous iOS version is still signed.

The purpose of jailbreaking is to disable iOS protections (Apple's code signing mechanisms in particular) so that arbitrary unsigned code can run on the device (e.g. custom code or downloaded from alternative app stores such as Cydia or Sileo). The word "jailbreak" is a colloquial reference to all-in-one tools that automate the disabling process.

Jailbreaking Considerations

Jailbreaking an iOS device is becoming more and more complicated because Apple keeps hardening the system and patching the exploited vulnerabilities. Jailbreaking has become a very time-sensitive procedure because Apple stops signing these vulnerable versions relatively soon after releasing a fix (unless the jailbreak benefits from hardware-based vulnerabilities, such as the limera1n exploit affecting the BootROM of the iPhone 4 and iPad 1). This means that you can't downgrade to a specific iOS version once Apple stops signing the firmware.

If you have a jailbroken device that you use for security testing, keep it as is unless you're 100% sure that you can re-jailbreak it after upgrading to the latest iOS version.

iOS upgrades are based on a challenge-response process (generating the so-called SHSH blobs as a result). The device will allow the OS installation only if the response to the challenge is signed by Apple. This is what researchers call a "signing window", and it is the reason you can't simply store the OTA firmware package you downloaded and load it onto the device whenever you want to. During minor iOS upgrades, two versions may both be signed by Apple (the latest one, and the previous iOS version). This is the only situation in which you can downgrade the iOS device. You can check the current signing window and download OTA firmware from the IPSW Downloads website.

{% hint style="danger" %} Updating the OS removes the effect of jailbreaking. {% endhint %}

Jailbreak Types

  • Tethered jailbreaks don't persist through reboots, so re-applying jailbreaks requires the device to be connected (tethered) to a computer during every reboot. The device may not reboot at all if the computer is not connected.
  • Semi-tethered jailbreaks can't be re-applied unless the device is connected to a computer during reboot. The device can also boot into non-jailbroken mode on its own.
  • Semi-untethered jailbreaks allow the device to boot on its own, but the kernel patches (or user-land modifications) for disabling code signing aren't applied automatically. The user must re-jailbreak the device by starting an app or visiting a website (not requiring a connection to a computer, hence the term untethered).
  • Untethered jailbreaks are the most popular choice for end users because they need to be applied only once, after which the device will be permanently jailbroken.

Jailbreaking Tools

Different iOS versions require different jailbreaking techniques. Determine whether a public jailbreak is available for your version of iOS. Beware of fake tools and spyware, which are often hiding behind domain names that are similar to the name of the jailbreaking group/author.

Version examples:

  • Checkra1n: Works on devices having the A7 chip and as new as the A11 chip, e.g. iPhone 5S up to iPhone X.
  • Palera1n: Checkm8 devices (A8-A11) on iOS 15.0-16.5.
  • Unc0ver: Only works only for iOS versions up to 14.8, since Apple patched the issues that allowed Unc0ver to run

The iOS jailbreak scene evolves so rapidly that providing up-to-date instructions is difficult. However, we can point you to some sources that are currently reliable:

Note that any modification you make to your device is at your own risk. While jailbreaking is typically safe, things can go wrong and you may end up bricking your device. No other party except yourself can be held accountable for any damage.

Benefits

The most important side effect of Jailbreaking is that it removes any sandboxing put in place by the OS. Therefore, any app on the device can read any file on the filesystem, including other apps files, cookies and keychain.

A jailbroken device allows users to install unapproved apps and leverage more APIs, which otherwise aren't accessible.

{% hint style="warning" %} It's not recommended to jailbreak the mobile for regular users {% endhint %}

After Jailbreaking

{% content-ref url="basic-ios-testing-operations.md" %} basic-ios-testing-operations.md {% endcontent-ref %}

Jailbreak Detection

Several applications will try to detect if the mobile is jailbroken and in that case the application won't run

  • After jailbreaking an iOS files and folders are usually installed, these can be searched to determine if the device is jailbroken.
  • In a jailbroken device applications get read/write access to new files outside the sandbox
  • Some API calls will behave differently
  • The presence of the OpenSSH service
  • Calling /bin/sh will return 1 instead of 0

More information about how to detect jailbreaking here.

You can try to avoid this detections using objection's ios jailbreak disable

Jailbreak Detection Bypass

  • You can try to avoid this detections using objection's ios jailbreak disable
  • You could also install the tool Liberty Lite (https://ryleyangus.com/repo/). Once the repo is added, the app should appear in the ‘Search’ tab
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