spaceraccoon.dev

Updated April 19, 2020: – Install OpenSSH through Cydia (ramsexy) – Checkra1n now supports Linux (inhibitor181) – Use a USB Type-A cable instead of Type-C (c0rv4x)

Updated April 26, 2020: – Linux-specific instructions (inhibitor181)

Updated August 14, 2020: – Burp TLS v1.3 configuration

Motivation

I wanted to get into mobile app pentesting. While it's relatively easy to get started on Android, it's harder to do so with iOS. For example, while Android has Android Virtual Device and a host of other third-party emulators, iOS only has a Xcode's iOS Simulator, which mimics the software environment of an iPhone and not the hardware. As such, iOS app pentesting requires an actual OS device.

Moreover, it's a major hassle to do even basic things like bypassing SSL certificate pinning. Portswigger's Burp Suite Mobile Assistant needs to be installed onto a jailbroken device and only works on iOS 9 and below.

For the longest time, iOS pentesting guides recommended buying an old iPhone with deprecated iOS versions off eBay. More recent efforts like Yogendra Jaiswal's excellent guide are based on the Unc0ver jailbreak, which works on iOS 11.0-12.4. If you don't have an iDevice in that range, you're out of luck.

Fortunately, with the release off the checkra1n jailbreak, A5-A11 iPhone, iPad and iPods on the latest iOS can now be jailbroken. Many iOS app pentesting tools, having lain dormant during the long winter of jailbreaking, are now catching up and new tools are also being released.

As such, I'm writing quickstart guide for iOS app pentesting on modern devices with the checkra1n jailbreak and consolidating different tools' setup guides in one place. I will follow up with a post on bugs I've found on iOS apps using the tools installed here.

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