iOS Penetration Testing Cheatsheet: Tools, Techniques & Step-by-Step Guide

Penetration testing, or “pentesting,” is an essential process to ensure the security of iOS devices and applications. In this iOS Penetration Testing Cheatsheet, we’ll cover the critical aspects of iOS penetration testing split into four phases: device security, data security, network security, and application security. Additionally, we will discuss essential tools for iOS penetration testing and provide examples for each.

1. Device Security

Device security is the foundation of iOS penetration testing. The first step is to gain access to the device’s filesystem. To achieve this, use tools like FileZilla, Cyberduck, itunnel, iProxy, and iFunbox.

FileZilla

Use FileZilla to access the device’s filesystem via SFTP:

filezilla sftp://username:password@IP_ADDRESS:PORT

Cyberduck

Use Cyberduck to access the device’s filesystem via SFTP:

open -a Cyberduck sftp://username:password@IP_ADDRESS:PORT

itunnel

Use itunnel to create a local port forwarding tunnel:

itunnel_mux --iport 2222 --lport 22

iProxy

Use iProxy to create a TCP connection from a local port to a remote port on a connected iOS device:

iproxy 2222 22

iFunbox

Use iFunbox to access the device’s filesystem. Simply connect your device, open iFunbox, and navigate the file system.

 

2. Data Security

Data security focuses on protecting the information stored on iOS devices. To examine and manipulate application data, use reverse engineering and static analysis tools like otool, Clutch, Dumpdecrypted, class-dump, Weak Classdump, IDA Pro, HopperApp, hopperscripts, and Radare2.

otool

Use otool to analyze the object files and executables:

otool -L /path/to/executable

Clutch

Use Clutch to decrypt and dump the application binary:

Clutch -d /path/to/application

Dumpdecrypted

Use Dumpdecrypted to decrypt an encrypted iOS app binary:

DYLD_INSERT_LIBRARIES=dumpdecrypted.dylib /path/to/encrypted_binary

class-dump

Use class-dump to generate header files from an iOS binary:

class-dump /path/to/binary -o /output/directory

Weak Classdump

Use Weak Classdump to dump class information for an iOS app:

weak_classdump.py /path/to/binary -o /output/directory

IDA Pro

Use IDA Pro to disassemble and analyze an iOS binary. Simply open IDA Pro, load the binary, and start the analysis.

HopperApp

Use HopperApp to disassemble and reverse engineer an iOS binary. Simply open HopperApp, load the binary, and start the analysis.

hopperscripts

Use hopperscripts to automate tasks in HopperApp. Note that hopperscripts are Python scripts that run within the HopperApp GUI. To use a hopperscript, open HopperApp, load the binary, go to the Scripts menu, and choose the desired script.

Radare2

Use Radare2 to perform static analysis and reverse engineering of an iOS binary:

radare2 -A /path/to/binary

3. Network Security

Network security entails securing the communication channels between iOS devices and external servers. To monitor and manipulate network traffic, use network analysis and server-side testing tools like Canape, Mallory, Burp Suite, OWASP ZAP, and Charles Proxy.

Canape

Use Canape to intercept and manipulate network traffic. Simply open Canape, configure the proxy settings, and start intercepting traffic.

Mallory

Use Mallory to intercept and manipulate network traffic between an iOS device and a remote server:

# Start Mallory with default settings
./mallory.py start

Burp Suite

Use Burp Suite to intercept and manipulate network traffic. Simply open Burp Suite, configure the proxy settings, and start intercepting traffic.

OWASP ZAP

Use OWASP ZAP to intercept and manipulate network traffic. Simply open OWASP ZAP, configure the proxy settings, and start intercepting traffic.

Charles Proxy

Use Charles Proxy to intercept and manipulate network traffic. Simply open Charles Proxy, configure the proxy settings, and start intercepting traffic.

4. Application Security

Application security involves assessing the security of iOS applications by analyzing their runtime behavior and detecting potential vulnerabilities. Dynamic and runtime analysis tools like cycript, Frida-cycript
, Fridpa, iNalyzer, Passionfruit, idb, snoop-it, Introspy-iOS, gdb, keychaindumper, and SSL Kill Switch 2 are essential for this process. Additionally, you can use tools like iOS TrustMe, Xcon, and tsProtector to bypass root detection and SSL pinning.

cycript

Use cycript to inject JavaScript into running iOS applications and analyze their runtime behavior:

cycript -p <process_name_or_pid>

Frida-cycript

Use Frida-cycript to inject JavaScript into running iOS applications using Frida’s instrumentation capabilities:

frida-cycript -U -f <process_name_or_pid>

Fridpa

Use Fridpa to automate the process of bypassing SSL pinning and root detection using Frida:

./fridpa.py -a <app_identifier>

iNalyzer

Use iNalyzer to perform dynamic analysis of iOS applications. Simply open iNalyzer, load the target application, and start the analysis.

Passionfruit

Use Passionfruit to perform dynamic analysis and interact with the runtime environment of iOS applications:

# Start Passionfruit server
passionfruit

idb

Use idb to analyze and manipulate the runtime environment of iOS applications:

# Start idb server
idb

snoop-it

Use snoop-it to perform dynamic analysis of iOS applications. Simply open snoop-it, load the target application, and start the analysis.

Introspy-iOS

Use Introspy-iOS to perform dynamic analysis of iOS applications. Simply open Introspy-iOS, load the target application, and start the analysis.

gdb

Use gdb to debug iOS applications at runtime:

gdb -p <process_id>

keychaindumper

Use keychaindumper to dump the contents of the iOS keychain:

./keychaindumper

SSL Kill Switch 2

Use SSL Kill Switch 2 to bypass SSL pinning in iOS applications. Note that SSL Kill Switch2 is a tweak installed through Cydia, so there is no command-line instruction. Simply install SSL Kill Switch 2 on a jailbroken device, enable it in Settings, and restart the target application.

iOS TrustMe

Use iOS TrustMe to bypass SSL pinning in iOS applications. Note that iOS TrustMe is a tweak installed through Cydia, so there is no command-line instruction. Simply install iOS TrustMe on a jailbroken device, enable it in Settings, and restart the target application.

Xcon

Use Xcon to bypass jailbreak detection in iOS applications. Note that Xcon is a tweak installed through Cydia, so there is no command-line instruction. Simply install Xcon on a jailbroken device and restart the target application.

tsProtector

Use tsProtector to bypass jailbreak detection and protect system files from being accessed by iOS applications. Note that tsProtector is a tweak installed through Cydia, so there is no command-line instruction. Simply install tsProtector on a jailbroken device, configure the settings, and restart the target application.

Conclusion

This iOS penetration testing cheatsheet provides a guide to help you secure iOS devices and applications. With the right tools and techniques, you can detect vulnerabilities, protect sensitive data, and safeguard network communication. By following this guide, you will ensure your iOS devices and applications are robust and secure against potential threats.

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