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Pen Testing Iphone Ipad iOS Applications

This document provides an overview of pentesting iPhone and iPad applications. It discusses the types of iOS applications, how they are developed and distributed, and tools for analyzing them like IDA Pro, SQLite Browser and Xcode. It outlines a methodology for pentesting iOS apps including preparing the device and workstation, intercepting network traffic, decrypting and reverse engineering apps. It demonstrates passive reconnaissance techniques like network capture and interception using tools like tcpdump, Burp and ADVinterceptor. It also shows attacks like intercepting communications and finding hard-coded passwords in apps through decryption and analysis of property list files.

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Dhiraj Patil
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© Attribution Non-Commercial (BY-NC)
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Download as PDF, TXT or read online on Scribd
185 views

Pen Testing Iphone Ipad iOS Applications

This document provides an overview of pentesting iPhone and iPad applications. It discusses the types of iOS applications, how they are developed and distributed, and tools for analyzing them like IDA Pro, SQLite Browser and Xcode. It outlines a methodology for pentesting iOS apps including preparing the device and workstation, intercepting network traffic, decrypting and reverse engineering apps. It demonstrates passive reconnaissance techniques like network capture and interception using tools like tcpdump, Burp and ADVinterceptor. It also shows attacks like intercepting communications and finding hard-coded passwords in apps through decryption and analysis of property list files.

Uploaded by

Dhiraj Patil
Copyright
© Attribution Non-Commercial (BY-NC)
Available Formats
Download as PDF, TXT or read online on Scribd
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Pentesting iPhone & iPad Apps

Hack In Paris 2011 June 17

Who are we?

Flora Bottaccio
Security Analyst at ADVTOOLS

Sebastien Andrivet
Director, co-founder of ADVTOOLS

ADVTOOLS
Swiss company founded in 2002 in Geneva Specialized in Information Security & Problems Diagnosis
Pentesting Security Audits Forensics Secure Development

Agenda
Overviews Previous researches iPhone/iPad application pentest
Our methodology

Live demonstrations Q&A

iOS Application Types


Web Applications
HTML + CSS + Javascript Run inside Safari

Native Applications:
Written in Objective-C (+ C/C++) Compiled into CPU code: ARM for actual devices, x86 for iOS Simulator

MonoTouch, Adobe Flash,


Written in high-level language Compiled into CPU code

iOS Applications
Distributed as .ipa files
in fact simply zip files

Deployed as .app directories


like on Mac OS X

Executable code is:


encrypted with FairPlay DRM (AES) signed with Apples signature decryption with GDB or Crackulous

Objective-C
Objective-C = C + Smalltalk Object oriented language Created in early 1980s by Stepstone Objective-C 2.0 released with Leopard (Mac OS X 10.5) Can be mixed with C and C++

Reverse Engineering
Not so obvious at first:
ARM instruction set Objective-C & objc_msgSend Generated code sometimes strange Few (working) scripts and tools

Finally not so difficult Your best friend:


Hex-Rays IDA Pro (Win, Mac, Linux)

Data storage
plist files (Property lists)
Used and abused Binary (depreciated) or XML

Sqlite 3
From time to time

Keychain Binary data files (aka unknown)

iTunes & Backups


Every time you connect your device to your computer, a backup is made Contains almost all data By default, not encrypted To mitigate security problems:

Previous researches
In general, out of date Often inaccurate But contain interesting information We will give here only some examples

Foundstone (McAfee / Intel)


Disappointing Assumes a lot In particular, assumes you have the source code If you have the sources, you make a code review, not a pentest

Nicolas Seriot

Not exactly on the same subject (about privacy) Excellent source of info However, a little out of date (everything is quickly out of date with Apple devices)

DVLabs (TippingPoint / HP)


Our starting point for decryption of apps Old (2009), some assumptions no more valid

ARTeam

About cracking, not pentesting Brilliant But very old now (2008 & 2009)

Previous Researches
Some interesting documents available Nothing specifically about pentesting iOS application and that is realistic and useable This is one of the reasons we make this presentation today

Pentesting iOS Applications


Step 1: Preparing a device Step 2: Preparing a workstation Step 3: Preparing a network Step 4: Pentesting Step 5: Report

Step 1: Device
Dedicated iPhone or iPad Jailbreak
Avoid iPad 2 for the moment

Install tools

Tools
Cydia APT 0.7 Strict adv-cmds Darwin CC Tools GNU Debugger inetutils lsof MobileTerminal netcat network-cmds nmap OpenSSH tcpdump top wget Crackulous

Default Passwords
By default, there are two users:
root mobile

Passwords = alpine Be sure to change them:


passwd passwd mobile

Step 2 : Workstation
Windows:
OK

Mac OS X (Snow Leopard)


Better

Linux, FreeBSD,
Good luck! Possible but you will need a Windows to run some tools (virtual machine)

Some Tools
Windows:
SecureCRT or Putty, WinSCP plist Editor for Windows

Mac OS X:
ssh, SecureCRT, Cyberduck XCode

Windows / Mac:
SQLite Database Browser Apple iPhone Configuration Utility Wireshark Burp / Webscarab / IDA Pro (+ ARM decompiler)

Our Tools
ADVsock2pipe
Remote network captures (Windows)

ADVinterceptor 2.0
Communications interception DNS & Web Servers

Will be released in June, 2011 GPLv3

Step 3: Network
Wifi
Internet

Firewall

LAN

Step 4: Pentesting
Step A: Install app. from iTunes Step B: Reconnaissance (passive)
B.1: Network capture B.2: Interception B.3: Artifacts B.4: Decrypt + Reverse engineering

Step C: Attack (active)


C.1: Interception + tampering

B.1: Network Capture

tcpdump + netcat

tcp ADVsock2pipe Windows pipe

B.2: Interception Proxy method

Proxy

Burp Suite Pro WebScarab

B.2: Interception ADVinterceptor

DNS HTTP HTTPS ADVinterceptor 2 (DNS Server, Web Server,)

etc.

Inject SSL Certificates


Root from Burp or ADVinterceptor Use Apple iPhone Configuration

Demos
3G+Wifi
Wifi 2G/3G

Internet

Wifi

VNC Client

Shell

SSH Client (SecureCRT)

Windows 7 on Mac Book

Demos
Goal is to illustrate the previous points, not to make a complete pentest This is also to show the catastrophic level of security of some iOS apps

Demo # 1
An application that stores securely password Data are encrypted except the password

Demo # 2
Network capture with
tcpdump netcap ADVsock2pipe Wireshark

Demo # 3
French application (passengers) Interception with proxy method & Burp Password in clear inside the SSL tunnel: not really a problem Password also in clear in a file (Property List): not good

Demo # 4
French retailer Interception with
ADVinterceptor + Burp

No SSL First message (CheckLogin)


Password encrypted with CRC64

Second message (Login)


Password in clear!

Thank you
To contact us:

www.advtools.com

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