iOS Application Security Part Three – Bypassing (Jailbreak and Certificate Pinning) Let the Right One In.

Welcome to my third article on “iOS Application Security Testing Series”. You can find Part Two here.

In this article, we will look at applications that use Jailbreak Detection and Certificate Pinning as defenses – and how they can be bypassed.

Is it a good idea to block execution on jailbroken or rooted devices? There is of course not a satisfactory answer to the question, and it depends on the app’s purpose and the information it handles (e.g. banks looking to add an extra layer of security) but one reason I have seen is application defects. So instead of fixing the problem, a blanket block policy is applied on all jailbroken device, regardless of malicious intent.

This is not an effective defense: checks need to be spread throughout the app to improve the effectiveness of the overall anti-tampering scheme.

Understanding Jailbreak Detection

For the most part, jailbreak detection procedures are a lot less sophisticated that one might imagine. While there are countless ways apps can implement checks for jailbroken devices, they typically boil down to the detecting of files and directories associated with jailbreaks, such as /bin/bash or /Applications/, or inspect File Permissions by attempting to create a file in, for example, the /private directory. If the file is successfully created, it means the device is jailbroken or checking Protocol Handlers like Cydia://

if([[UIApplication sharedApplication] canOpenURL:[NSURL URLWithString:@”Cydia://package/com.example.package”]])

By checking the exit status of fork() reading-through the returned pid on fork(), an app can detect if it has successfully forked. If the fork is successful, the app can deduce that it is running on a jailbroken device. There are some more advanced methods as well such as checking the existence of certain known dylib’s too (which is the hardest to circumvent). The best graphical details of the techniques can be found here but for this post, I’d like to go with a real-world application  “Twitter” and show the techniques mentioned.


Twitter has a bounty program under so bounty rules apply.

Bypassing Jailbreak Detection

  1. The application closes immediately without any notification
  2. There is a popup window indicating that the application won’t run on a jailbroken device

In the first case, it’s worth checking if the application is fully functional on a non-jailbroken device.

Swift vs Objective-C

Since Objective-C and Swift are fundamentally different, the programming language in which the app is written affects the possibilities for reverse engineering it. For example, Objective-C allows changing method invocations at runtime.

This makes it easy to hook in other functions in an app, which is heavily used by Cycript and other reverse engineering tools. This “method swizzling” is not implemented in the same way in Swift, which makes it harder to do than in Objective-C. Most tools that currently work well with Objective-C are working on improving their compatibility with Swift. For example, Frida currently does support Swift bindings.

Discovering the implementation

First, we start with disassembling the app. In order to disassemble any app from the App Store, it must first be decrypted (“Cracked“), even if it is a free application.

Apple injects a special 4196-byte long header into the signed binary encrypted with the public key associated with your iTunes account. This is part of Apple’s Fair-Play DRM but the Fair-Play copy protection has been cracked some time ago.

I have mentioned Cycript in part one here. It is a scripting language developed by Jay Freeman (saurik). Cycript injects a JavaScriptCore into the running process but first, we can use Clutch to decrypt the binary.

the Clutch -I list apps installed from the App Store (as you can see, I have 3 apps installed)

Let us just run Clutch -b 2 command to proceed.

After Clutch decrypts, we can easily load the binary into a disassembler, e.g., IDA Pro or an awesome disassembler called Hopper, to identify methods of interest.

Technique for Dumping Class Information  

Normally using class-dump-z on the application’s decrypted binary will dump all of the header files. Occasionally, these contain “giveaway” method names, like “deviceIsJailbroken” or “checkDeviceSecurity.”

To find the decrypted binary just run the find command as following: “find  -name *Twitter “and as you can see in the picture below there are two interesting directories in the /tmp/Clutch

We found the application locations in ./tmp/clutch/B277F488-E9E8-446C-8915-0077C0068E48/com.atebits.Tweetie2/Twitter and./tmp/clutch/B277F488-E9E8-446C-8915-0077C0068E48/com.atebits.Tweetie2.t1twitter/T1Twitter

Here is the anti-tampering defence message I got when I ran class-dump 😊

But it can easily be bypassed using Snoop-it or Class-dump-z.

Techniques showed above are very convenient and gives one a deeper understanding but nowadays, anyone can install third-party apps on emulators without having to use the date trick to bypass Apple’s restrictions. Thanks to Nintendo’s there are several working Nintendo DS emulators available here, though still at an early stage No jailbreak is required.Really!

Certificate Pinning What is It?

Certificate pinning is hardcoding or storing the information for digital certificates/public keys in a mobile application. By default, when making a TLS connection, client checks that the server’s certificate:

  • Has a verifiable chain of trust back to a trusted (root) Certificate.
  • Matches the requested hostname.

What is the problem?

The device’s trust store can easily be compromised – the user can install unsafe certificate 2011 DigiNotar attack., thus allowing potential man-in-the-middle attacks (simply put relies on the client side) –Certificate pinning is the solution to this problem. Certificate pinning prevents this by ensuring a specific server public key is used to initiate secured traffic with hosts that have signed exact certificate inside the application.

Bypassing Certificate Pinning

The first step is to set up an intercepting proxy (Burp Pro) showed in part one here and the SSL Kill Switch installed and configured to use your laptop as the device’s proxy. SSL Kill Switch –Leverage’s Cydia substrate and uses MobileSubstrate to inject on the process which in subsequent hooks on SecTrustEvaluate .


Installing this tweak allows anyone on the same network as the device to easily perform man-in-the-middle attacks against any SSL or HTTPS connection.

You can download the latest pre-compiled Debian package available in the release section of the project page at

 How to install

Download and copy the Debian package to the device; install it as followed:

This works great against Twitter and even goes deeper when intercepting system daemons like accountsd.


In this article, we looked at applications that use Jailbreak Detection and Certificate Pinning as defenses – and how they can be bypassed.

How Do I Prevent and what are the Best Practices (Taken from Owasp 2016-M9 )

Default classes in the latest version of iOS handle SSL cipher strength negotiation very well. Trouble comes when developers temporarily add code to bypass these defaults to accommodate development hurdles. In addition to the above general practices:

  • Ensure that certificates are valid and fail closed.
  • When using CFNetwork, consider using the Secure Transport API to designate trusted client certificates. In almost all situations, NSStreamSocketSecurityLevelTLSv1 should be used for higher standard cipher strength.
  • After development, ensure all NSURL calls (or wrappers of NSURL) do not allow self-signed or invalid certificates such as the NSURL class method setAllowsAnyHTTPSCertificate.
  • Consider using certificate pinning by doing the following: export your certificate, include it in your app bundle, and anchor it to your trust object. Using the NSURL method connection:willSendRequestForAuthenticationChallenge: will now accept your cert

More resources


About Liban Mohamud

My name is Liban Mohamud, I hold M S.c in Digital Investigations, Forensics and Computer Security from University College Dublin (UCD). I’m an Information Security Specialist and researcher with a passion for Mobile Security and Mobile Forensics and I have over 15 years experience in the industry. @coolx28

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