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    iPhone Application Development Security

    Top 5 iPhone Application Development Security Issues

    Posted: May 4, 2010 – 8:24 am | Author: jeremy.allen | Filed under: Uncategorized
    Since Apple released the iPhone in 2007, it has become one of the most dominant mobile phones in the market. The iPhone has seen quite a few significant platform security issues along the way. There has been a continual effort on jail breaking (gaining complete control over) the iPhone, and unlocking it. Much of the security news related to the iPhone focuses on the platform itself, while less attention has been paid to individual applications in the app store (and how they are developed). What are the most common security risks affecting iPhone applications? Based on our experience testing iPhone applications we have compiled a top 5 list of security issues for developers:

    1.) Sensitive data unprotected at rest – Mobile applications cut right to the heart of software functionality to provide what users absolutely need when they are on the move. For many applications, this can involve displaying, or even storing, sensitive data. Many iPhone applications read and display sensitive data, such as medical lab test results, or personal and business oriented financial data. For example, the Care 360 Mobile iPhone application allows doctors and medical professionals to retrieve and view lab results from Quest Diagnostics. Many large banks also provide mobile applications to provide better user experience than the Safari web browser for online banking. These applications handle some of the most sensitive data (medical and financial) most users will ever possess. Additionally, many applications also provide a variety of “remember me” functionality. Keeping this data secure and out of the hands of a malicious adversary is therefore of paramount importance for both the user and the application provider.

    The solution to this problem is careful architecture design with a risk-based approach to help decide the security posture the application has towards data storage. Once the risk has been determined, it is essential to protect sensitive data that must reside on the device using a combination of strong cryptography and the Apple Keychain services, or equivalent cryptographic constructs, to protect this sensitive data while at rest.

    2.) Buffer overflows and other C programming issues – The iPhone development platform is primarily Objective-C based. Objective-C provides a much cleaner environment for the programmer when compared to C. It inherently prevents many common C programming errors, which can result in exploitable bugs and flaws in an application. If a developer writes an application purely from within the confines of Objective-C using the Foundation, UIKit and other pure Objective-C frameworks, the application is relatively safe from most of the security issues that afflict C programs. For example, the NSString class prevents buffer overflow bugs effectively in most cases (assuming there are no flaws in the underlying NSString implementation). Another key point to the pure Objective-C environment of the iPhone is the fact that all object allocations go on the heap, which helps prevent stack overflows since directly programmer controlled memory does not live on the stack. The developer is responsible for allocating and deallocating objects, but the complexity is largely hidden from the developer compared to a C implementation.

    However, some parts of the iPhone SDK require the developer to revert to standard C. This is an all bets are off proposition that eliminates the safety provided by the Objective-C platform. It is common to build and include C libraries in an iPhone application to avoid re-implementing code (and it is often the right choice from a time to market standpoint). This means going from relatively safe Objective-C libraries and moving to less safe C style strings for libraries like SQLite, a core part of many iPhone applications, and . Buffer overflows are one of the various issues that plague C programs. Vulnerabilities can stem from heap overflows, format string attacks, integer overflows, and other more subtle issues that are relevant when developing in C for iPhone.

    Generally avoiding C libraries when at all possible is ideal. However, when C and C libraries are required developers must follow best practices derived over the lifetime of the C programming language. When observing best practices mistakes may still occur. Development teams must use safe string libraries and individual developers must understand the risks and vulnerabilities that can occur when writing code in C.

    3.) Secure communications to servers – Almost every useful application that handles sensitive user data will connect back to some server component. Developers are, thus, faced with the challenge of having to protect sensitive data in transit as it traverses the Internet and sometimes even insecure wireless media. This is done using encryption; that must be implemented correctly.

    Effective encryption entails avoiding reinventing the wheel and using trusted libraries that have been thoroughly reviewed. The iPhone SDK is, largely, like any other SDK regarding its SSL libraries. Developers must take care when using the URL loading library as the way the applications use the libraries in a development build or configuration will typically differ from proper usage in production. The default state of operation for the URL loading library is to fail on an invalid server certificate. However, during development it is often required to use an invalid certificate. Failure to use the libraries properly can result in weak client to server communications that allow a malicious adversary to compromise client to server communications.

    4.) Patching your application – The App Store could be your worst enemy, a proper risk assessment of an organization’s tolerance for risk should be conducted to determine if the app store policy will match up with, and be acceptable, for any given application. Apple maintains tight control over the App Store and it will not be possible to issue a release in a very short (24-48) hour period in most cases. The Apple approval process generally takes at least a week. If the application has any issues that would cause it to fail, the approval process of the new build could take weeks to reach customers.

    Unfortunately, there is very little that an organization can do regarding the risk associated with this issue. The best bet is to ensure that developers have a clear understanding of app store policy and that the testing process is thorough and proactively identifies issues that would cause the application to fail the approval process.

    5.) The platform itself – User awareness is also a critical component of application security. Users often perceive and treat their mobile, Internet connected, devices with a different level of care compared to a laptop or desktop. Password policies, anti-virus software, and at least some awareness that their computer may contain sensitive data and that it requires protection is the norm for most users. Mobile devices are often lost, not password protected and get treated with a lower level of security awareness. This means that a user could easily lose their phone to a malicious individual and have their sensitive data compromised.

    Thus, it is important to attempt to raise the mobile user’s awareness of the risks they are exposed to through well constructed documentation and application design. A mobile user that is more security conscious may take efforts to secure their environment more, such as by using a PIN or pass phrase to secure their device, and subscribing to Apple services that can help locate and disable lost or stolen devices. From a developers perspective the key thing is to alert the user when they are making security sensitive actions via visual cues and or dialogs/text. Users will generally do whatever is quickest and easiest for them. Developers must design these features to be as unobtrusive as possible.

    iPhone Pen Testing Security Tools

    http://www.taranfx.com/iphone-pen-testing

    Modern smartphones have enough horsepower to do just about most of the stuff you do on your PC.

    There are apps for everyone, but no one really bothered about Security expperts/admins/ network gurus. Nickmpetty thought about this and compiled a list of apps that will do this right for security geeks, Pen testers. You can simply install all the popular pen testing tools to your iPhone, iPod Touch, iPad and connect an external keyboard (if you need to) or use it wirelessly via a SSH client like putty and there you have it — A Portable powerful pen-testing tool.

    So here is the suite of Pen Testing Tools for all those who own an iPhone/ iPod Touch

    Pre-Requisites: Jailbreak your iPhone, iPod Touch, iPad

    Note: You must use ‘Developer Mode’ in Cydia. If you didn’t, go to Manage, then click on settings in the top left corner, and select it there.

    OpenSSH

    If you have a jailbroken iPhone, this would be something you already have.

    Mobile Terminal

    Mobile terminal gives you the full shell access, it provides bare bones for the most of the stuff.

    Building a Linux Shell

    With the basic stuff in there, lets install some base tools and packages that are normally included on a normal linux computer.

    How to Install From Cydia, Install “uzip, adv-cmds, aptitiude, apt 0.6 transitional, inetutils, iPhone/Python, make, subversion, wget, iDNS, stunnel, tcpdump, setup tools, ruby, OpenSSH, OpenSSL, MetaSploit”.

    Perl

    In terminal (or via SSH) login as root with the “su” then install using “apt-get install perl” or via Cydia. Execute “curl -O http://coredev.nl/cydia/coredev.pub”. Next, run “apt-key add coredev.pub”. If you get an error, just ignore it. Now type, “echo ‘deb http://coredev.nl/cydia iphone main’ > /etc/apt/sources.list.d/coredev.nl.list”. Then, “apt-get update”, and “apt-get install perl”. Thats it. You can now delete that coredev.pub file.

    Installing Pen Testing Tools

    Create a folder called ‘pentest’ anywhere e.g. /var/root/. Try isntalling all the apps in this directory so that you have all the tools handy at one place.

    Ettercap-ng

    Ettercap is a suite for man in the middle attacks on LAN. It features sniffing of live connections, content filtering on the fly and many other interesting tricks. It supports active and passive dissection of many protocols (even ciphered ones) and includes many feature for network and host analysis.

    How to Install Install from Cydia, if you can’t find it, Add this source “theworm.altervista.org/cydia”.

    aircrack-ng

    Aircrack-ng is an 802.11 WEP and WPA-PSK keys cracking program that can recover keys once enough data packets have been captured. It implements the standard FMS attack along with some optimizations like KoreK attacks, as well as the all-new PTW attack, thus making the attack much faster compared to other WEP cracking tools.

    How to Install Search for “aircrack”, if you can’t find it try adding source to Cydia, “http://cydia.xsellize.com”. Once you’ve installed it, an icon will appear on SpringBoard, don’t bother with it. Its only to tell you to run aircrack from the terminal. Navigate to /var/aircrack/ to use it.

    Nikto2

    A web server scanner which performs comprehensive tests against web servers for multiple items, including over 6400 potentially dangerous files/CGIs, checks for outdated versions of over 1000 servers, and version specific problems on over 270 servers.

    How to Install We need SVN to get the source and build it. execute “svn co http://svn2.assembla.com/svn/Nikto_2?. It will download the folder, move it to pentest and then navigate to the nikto2 folder, and the next folder then execute as normal.

    SET (Social Engineering Toolkit)

    The Social-Engineering Toolkit (SET) was designed by David Kennedy (ReL1K) and incorporates many useful Social-Engineering attacks all in one simplistic interface. The main purpose of SET is to automate and improve on many of the social-engineering attacks out there. As pentesters, social-engineering is often a practice that not many people perform.

    How to Install SET is every geek’s fav. You need to checkout via svn “svn co http://svn.thepentest.com/social_engineering_toolkit/ SET/”

    Move it to your pentest folder, then SET, and go as normal once again.

    NMap

    Nmap (“Network Mapper”) is a utility for network exploration or security auditing. Many systems and network administrators also find it useful for tasks such as network inventory, managing service upgrade schedules, and monitoring host or service uptime. Nmap uses raw IP packets in novel ways to determine what hosts are available on the network, what services (application name and version) those hosts are offering, what operating systems (and OS versions) they are running, what type of packet filters/firewalls are in use, and dozens of other characteristics.

    How to install Search for it in Cydia, its already there.

    This just the beginning, you can get a number f other security tools, just search in Cydia.

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