We take a look at Elcomsoft iPhone Password Breaker… Its Good

Elcomsoft are a Russian based software company, who make excellent security and audit products. Perhaps the name doesn’t ring a bell, but I am sure if you look at their product offerings you will be more than familiar with their products.

I first heard about Elcomsoft around 2002 I think it was when I needed to do some password recovery for some Office documents, and a colleague had a copy and it did its magic and we had a happy user. Ever since then I have kept the site bookmarked and keep a check on it every now and again.

Fast forward to 2010 and I find myself looking at iPhones and their suitability for use in the corporate world, and then I hear again about Elcomsoft releasing an iPhone Password Breaker (EPPB). So here we are, reviewing this product, and seeing just how it works and if it does what it says on the tin.

At the time of writing the professional version is advertised at £199 and the home version at £79. To see the difference between the version, please see the end of the review, or click here to visit the Elcomsoft site.

Thanks to the guys at Elcomsoft for letting me have a copy to review, and for helping resolving any issues I came across on the way.

So first things first, the EPPB requires a Windows Platform, so I fired up an XP SP3 VM, and a physical W7 box to do some GPU based testing.

Once its installed we need to get hold of our encrypted iPhone backup. So the main file we are looking for is the Manifest.plist file, however if you will want to look at the keychain info you will want the complete contents of the appropriate folder.

When iTunes takes a backup of your iPhone it will include your settings files, from the preferences library, and databases, such as your calls, notes, bookmarks, password etc.

So if your on a Mac you need to look here > /Library/Application Support/MobileSync/Backup
On a PC you need to look here > Documents & Settings\\Application Data\Apple Computer\MobileSync\Backup or Users\\AppData\Roaming\Apple Computer\MobileSync\Backup

So once you have located your encrypted backup its time to fire up the password breaker and point it at the file in question. You will see the details of the device once you have selected it. We can see in this example the backup is that of an iPhone 4.

Now we have our file selected, lets make sure we are using the right hardware. So now we can enable / disable our CPU and GPU options.

So now the hardware is selected, we are almost ready to get cracking :) Now we just need to decide how we are going to go about it. We can use dictionary based attacks and supply files with the information (although it does come with some) or we can configure some brute force settings.

So now we are all configured, and lets face it, its all easy and straight forward. Now we kick off the cracking and watch the speed.

In the image below I am using a dual core Intel 3Ghz processor and a ATI Radeon 5880. As you can see its 15,108 passwords a second, not to shabby at all. My quickest crack was a 7 character dictionary password that was popped in 2.33 secs, GPU for the win. I also tried just a 64Bit Athlon 3Ghz on its own, and it only did 102 passwords a second, I also tried a 2.8Ghz Dual Core Intel in a VM and saw about 300 passwords a second, I then finally tried a cheaper GPU, a NVIDIA 8800 GTX and this provided the power to crunch 3,804 passwords a second.

So now we have the password for this backup. We can now open the file in iTunes and complete a restore if we had forgotten the password. Or we can launch the keychain explorer and have a look at the information stored within the backup from the iPhone, as well as exporting the contents to an XML file.

Obviously I have sanitised the screen shot as it contains information I dont want to share, but you are going to see details of services used, usernames and passwords, access point information and access passwords, phone numbers and more.

So you may be thinking this is all good, but why is this tool of interest to me. Well first of all, as I have mentioned before many organisations are looking at, and are deploying iPhones. Out of the box they are not an enterprise ready tool and require 3rd party enterprise tools. So you get a call from you user, the iPhone needs restoring, they dont want to lose their information so they want to restore from the backup. Fine, however they have forgotten their password. So now you have an option to recover with this tool.

Next is the addition of gathering this information as part of a penetration test, or even a social engineering engagement. Obviously you need to get the files off the users machine, not the iPhone itself. I don’t need to tell you guys the ways this is possible. If your feeling really lazy, you may want to check file sharing networks, people share all sorts.

If you are a file sharing network user, please check you are not sharing your entire hard disk, and if you are…. STOP IT.

To conclude I think this is a tool worth having if your organisation is offering the use of iPhones, and it also has a place in your pentesting toolkit. For more information check out Elcomsofts website, and read below for some more information on the tool itself.

Elcomsoft iPhone Password Breaker enables forensic access to password-protected backups for iPhone, iPhone 3G, iPhone 3GS, iPhone 4, iPad, and iPod Touch 1st, 2nd, and 3rd Gen devices. Featuring the company’s patent-pending GPU acceleration technology, Elcomsoft iPhone Password Breaker is the first GPU-accelerated iPhone/iPod password recovery tool on the market. The new tool recovers the original plain-text password that protects encrypted backups containing address books, call logs, SMS archives, calendars, camera snapshots, voice mail and email account settings, applications, Web browsing history and cache. The program is also able to read and decrypt keychains (saved passwords to mail accounts, web sites and 3rd party applications) from password-protected backups (if password is known or recovered).

  • Gain access to information stored in password-protected iPhone and iPod Touch backups
  • Recover the original plain-text password
  • Read and decrypt keychain data (email account passwords, Wi-Fi passwords, and passwords you enter into websites and some other applications)
  • Save time with cost-efficient GPU acceleration when one or several ATI or NVIDIA video cards are installed
  • Hardware acceleration on Tableau TACC1441 hardware
  • Perform advanced dictionary attacks with highly customizable permutations
  • Perform offline attacks without Apple iTunes installed
  • Recover passwords to backups for original and ‘jailbroken’ iPhone, iPhone 3G, iPhone 3GS, iPhone 4, iPad, and iPod Touch 1st, 2nd, and 3rd Gen devices
  • Compatible with all versions of iTunes (incl. 10.0) and iOS (3 and 4, incl. 4.1)

Elcomsoft iPhone Password Breaker supports Windows XP, Windows Server 2003, Windows Server 2008, Windows Vista or Windows 7 with x32 and x64 architectures. Password-protected backups to iPhone, iPhone 3G, iPhone 3GS, iPhone 4, iPad, and iPod Touch 1st, 2nd, and 3rd Gen devices are supported.

iPhone Security.. Does it exist??

I am not currently an iPhone user, but its clear that for many reasons they are a smart phone of great desire. Many of the customers I work have have shown an interest in deploying iPhones in their corporate environment. The reason being… well that often seems to be a difficult one for them to answer. I dont think they know really, perhaps they like the idea of developing some internal apps, or perhaps they like the idea of a trendy device.

Now I am all about helping people make an informed decision regardless of if I agree or not, so this got me into looking at the state of iPhone security (pre iOS4) and its not so good. Personally I think the iPhone is great for the user on the street (33% of smart phones globally are iPhones), but letting it lose in the corporate environment, against established Black Berry devices and alike, is surely madness?

I am not going to go into any great detail here, as a blog post is really not the place, but hopefully the information below will paint a small picture of concerns about using an iPhone in the corporate environment. If your interested in doing more research check out iPhone Forensics by Jonathan Zdziarski, as well as checking out his tutorials online. There was also a recent SANS Webcast on iPhone security also, and this also shared the same thoughts that I have, from investigations and information found online. I will also be doing another post on the security benefits iOS4 has brought, and how it does or doesn’t change the iPhones suitability in a corporate environment. Also check out CESG’s declaration of no iPhones allowed in Whitehall posted on The Register.

My main issue with iPhones for corporate environments, aside from the below is that there is no real enterprise management tooling. Yes some things can be improved with the use of the iPhone Configuration Utility, but this is a local process, and requires other tooling to distribute the config files. You can get some more additional control and reporting if you incorporate exchange, and maybe MobileMe. Also dont forget iTunes is also required, how many corporate standard builds feature iTunes?? I just cant see why companies consider the iPhone when compared to established offerings like Black Berrys, with its full enterprise suite of tools.

iPhones can be Jailbroken – This is the term associated with unlocking the restrictions applied to an iPhone, allowing any code to be run regardless of its approval by Apple or any other organisation, another advantage is that a Jail Broken iPhone also removes the ability for the remote removal of applications via Apple. Its is estimated that around 10% of iPhones globally are Jail Broken, the reason for this is most likely that others are worried about the voiding of warranty, as well as restricting the application of future updates from Apple. As well as opening your iPhone to using more programs, and enhancing its use, Jail Breaking also reduces the security of your iPhone if you are not security savvy. This was
demonstrated in late 2009 when a hacker released a worm targeting Jail Broken iPhones, there have also been other reports of viruses on Jail Broken iPhones compromising banking
transactions.

iPhone OS (pre iOS4) – All popular operating systems have security issues, and the iPhone OS has its fair share of vulnerabilities. The latest OS updated 46 currently known vulnerabilities; the reality is that as the iPhone grows in popularity and becomes adopted by organisations the incentive and reward to find and exploit vulnerabilities will continue to grow. A new feature or some would say security flaw with the iPhone OS that was discovered in May 2010 is the automatic mounting of the iPhone’s memory when connected via USB to a Linux based machine. This bypasses any controls, PINs and encryption set on the device and gives a limited access to the iPhones storage. I believe the primary goal was to allow iPhones to be used easily with Linux distributions, however obviously this brings with it serious security concerns.

The Apple App Store – The Apple App Store provides the single official point of contact for all applications on the iPhone. The idea behind this is to ensure that all applications are safe for use, and there are currently around 235,000 applications approved for download. Apple have confirmed that around 10% of applications submitted to the App Store have components within them that will aim to steal data. With this in mind, I would suggest that it is unlikely that Apple are able to 100% guarantee that all applications available have been fully tested and defined as safe. In fact it has been known that Apple occasionally remove applications from the App Store, and people’s devices, after making a decision to recall specific applications for various reasons. There are also various theories on how an application could be made available on the App Store, and obfuscate its real intention to steal data. The point to be made here, is that applications could potentially steal corporate data, regardless of their supposed safety approvals from Apple.

Passcodes and Pin Numbers – Most smart phones use a passcode, or PIN number to restrict the physical access to the device. iPhones do have this feature, however it is restricted as standard to only being 4 digits. This is obviously not a good situation, however the situation is made worse with multiple ways to bypass the passcode requirement all together. Some methods require the use of a computer, while others can be done stand alone in less than two mintues. This then gives full access to the device, contacts, emails etc, as if you have
entered the appropriate code.

Encryption – Until the release of the iPhone 3GS there was no encryption available on the device. The 3GS now features full hardware encryption of the device’s contents. Once again
with physical access it is possible to make a copy of the entire contents of the device, and circumvent the encryption, all of this is easily possible in fewer than 5 minutes. Just check out YouTube.

System Data – The iPhone stores a lot of data classified as system data. Even though applications run in a sandboxed / isolated environment there is still some leakage that occurs
when obfuscation is used within a program’s code. The system data contains a large amount of information, email parameters, names and addresses, but no passwords or messages. In
addition all keyboard entries (except for password fields) are cached and stored, along with address book entries, the last 20 sites browsing history, WIFI network history, as well as
images and their associated data, time, data, location. An interesting feature is that every time the home button is pressed on the iPhone to return to the home menu a screen shot is
taken, containing all the information on the screen for that application at the time, this is also saved and stored as system data. In addition to this VoiceMails can also be stored as system data. All of this system data can be accessed and backed up with physical access, as discussed before with encryption bypassing. An application that steals data would also have
access to this data, and could transmit the information over a Wifi network, or mobile Internet.

Finally, just as a reminder, these are just my opinions and thoughts, based on research and findings. I do like Apple products, I have a few :) However I am still not sure its ready for the corporate environment. Perhaps after reading about ALL the proposed iOS4 updates I will change my mind.

DESlock+ Enterprise Review

Last year (2009) I got a call about reviewing a Full Disk Encryption product called DESlock+. I had not heard of the product, so a quick search later and more information was revealed. As encryption is an import consideration for users at home and within an organisation, and I had been looking at a few vendors for my day job I thought it would be some time well spent, and may be of use to some of you guys.

DESlock+ Enterprise is the product I am going to be look at, and its made by a company called DES. DES were founded in 1985, and the companies systems and methods originated within the British Government Communications Headquarters. The original users of DES products were government based, but over time have spread into other sectors. Over the past twelve years DES has also marketed the DESkey and DESlock range of software protection products. With an estimated 500,000 units in use throughout the world to date, sales of the DESkey continue to grow.

  • Full Disk Encryption
  • Removable Media Encryption
  • Encrypt Email, folders and files
  • Multiple encryption keys stored in a keyfile
  • AES, 3DES, Blowfish Algorithms
  • Encrypted mountable files
  • Secure data shredder
  • Keyfile backup utility
  • Scalable centralised licence and key management
  • Remote keyfile distribution
  • Software feature policy control
  • Includes DESkey USB manager tokens

When reviewing encryption products its can often be a difficult task. Lets face it the most important thing an encryption product can do is encrypt, if it doesn’t do that then we are in a pretty bad situation. So you will be happy to hear DESlock+ does encrypt and it works in a no nonsense way so with that in mind we are off to an excellent start.

To speed up my review Jamie Gordon (excellent guy) sent me a Windows 7 Virtual Machine with the DESlock product pre-installed, as like everyone getting the time to have a look at a product can be difficult. So the starting situation is essentially this. We have a Windows 7 client machine that has DESlock+ installed, and connecting back to DES HQ. The client gets its policy applied when we start up and authenticate for the first time, and we have various options available to us, but the Full Disk encryption has not yet been applied, our friend Jamie takes care of that for us remotely later.

I have a hell of alot of screenshot, about 120 or so, obviously I don’t want to post all of these, so as part of this review I will give an overview of whats going on, various configuration and functional options. I can tell you now the best thing for me about DESlock+ is it does what it says on the tin, with no fuss, and you don’t need to be a rocket scientist to configure your policy and get it up and running. I will basically show the shredder options, encrypting individual files, removable media and of course full disk encryption.

So to get things started we boot up our VM. Its important to remember that normally in an enterprise environment you would normally be logging onto a domain, however in this example this is not the case. So any credentials are not resolved from my domain credentials, its needs to be done manually. So I need to authenticate myself with the DESlock+ Enterprise Server using a one time password to get things started.

Once authenticated we need to change the password.

So now we are presented with the Desktop to go about our daily duties. Its worth noting we have the features of DESlock+ available to us now, but we have not yet had our hard disk encrypted.

So everything looks as normal, although we have the DESlock+ Shredder, and a couple of new icons in the task bar.

I will add a picture montage at the end of this review that shows various screen shots, so if you want to know what happens when you look further at these properties you can check them out.

So lets see what happens when I plug in a USB stick (A Dell branded 64Mb in this case). DESlock+ detects the USB device and prompts to do its thing.

So lets kick off the removable device encryption.

Encryption Completed.

Once the drive was encrypted a put a couple of files on there, ejected the drive and tried the stick on a windows machine, linux and Mac. All found the drive to be unreadable, so no chance at getting at that data. So good stuff.

So next I decided to decrypt the drive, and then try just encrypting a single file.

So now we create a file, and right click for our encryption options.

Once the file is encrypted the remainder of the stick was still usable, but as expected the encrypted file is not accessible. Obviously files can be encrypted like this locally, as well as on removable media. This allows for some versatile application, whilst ensuring control and protection over your data.

Of course for that little bit of additional protection its a good idea to securely erase files when your done with them, and this brings us along to the DESlock+ Shredder. You can choose how many passes you want to make when erasing the data, and choose between two methods.

So we know we can encrypt our files as needed, and we can securely erase them also. So the next thing to get sorted is obviously full disk encryption.

There is an option to encrypt using a local wizard, and an activation code you get from the administrator. I did have a look at this option as the screen shots below show. However I decided to go the remote route as this is an enterprise offering, and see how it works from the admin console.

As you can see above. If we had an authorisation code from our admin, we could kick off the full disk encryption ourselves.

So now lets take a brief look at what we see as an administrator from the DESlock+ Enterprise console.

Once we are in the admin console we have access to the various configuration options. We have the ability manage both DESlock vouchers (these control what you can or cant do based on what you have purchased) and users of the system. From a day to day perspective this is probably where you will spend time verifying what accounts are created, active machines and so forth when your first getting set up. Then there is the profiles section, this does what it says on the tin. It allows the for creation, modification and assigning of encryption profiles. Next is the Enterprise server section, this shows the user details and associated machine, when they last connected, keyfiles in use etc. The full disk encryption section is fairly obvious, this where you manage the FDE of machines in your environment. We then have the encryption keys section, this is a useful section as you can create multiple encryption keys for different parts of your organisation, to give extra levels of control. Finally the install admin section, this pulls various information together to form a registry key that is applied as part of the product install on client machines.

I viewed this section remotely with the DES guys, so I didn’t have time to have a proper play myself, but I did take some snapshots that you can see towards the end of the review.

So whilst viewing remotely, Jamie kicked off my remote encryption of my VM machine. It worked a charm with no fuss. My machine connected with the remote server, downloaded configuration updates, and then started encrypting. I even rebooted mid encryption as a test and it resumed once logged in.

So here are a couple of snaps to show what’s going on at the client end.

Now lets reboot.

Job Done :)

Wrap up and thoughts….

So we have gone through the motions, seen some screen shots, but is it actually any good. Personally yes I think it is. For me when it comes to encryption products it can be a difficult evaluation process, because lets face it if its encrypting our data in a secure method its ticking the box. I think what makes DESlock+ a good product is that its simple. I don’t mean that in a negative way at all, the product does what it says on the tin. It encrypts files, removable media, full disk encryption as well as emails and other bits and bobs I was not able to spend time in testing, and it does it in a professional no fuss approach. The menus and clear and simple to understand, policy configuration is easy and flexible, I like the fact you can use different encryption keys in different parts of the business, and for different users, this gives an extra level of access control. I like how easy it is to revoke access to encrypted files and devices in the event of loss, and I like the challenge response stuff for when people forget passwords and I like the secure deletion with the shredder.

I would certainly make organisations (especially SME’s) I work with aware of DESlock+ as well considering their similar home offering to family and friends who just want to encrypt files and don’t need FDE. However as with everything I had a few gripes with the product whilst reviewing. Its great that you can encrypt removable media, but its abit frustrating you cant share the content with non DESlock+ customers (they now have an offering for this coming soon), and I have seen some other products that allow custom configuration messages for users screens, this isn’t a major one for me but its a bonus sometimes. Lastly its my understanding that the product itself does not support distribution across the organisation, so you need to utilise some other tooling to package up and distribute DESlock+. None of this stops me thinking its a good tool, just sharing my thoughts. It is also worth noting the DESlock+ products only work on W2K upwards, so no support for Linux and OSX.

Since I have completed the review DESlock+ has been FIPS 140-2 validated, so congratulations and well done to the guys on that achievement. They have also made a product available called DESlock Reader which will allow non DES customers to decrypt emails, and files that have been encrypted with DESlock+ (obviously you will need to know a pre shared password to decrypt), this something that can be enabled or disabled at a policy level if you don’t want everyone having the ability to potentially share data outside the organisation. Another product is in the pipeline that should be out later this month, and this is DESlock+ Go. This product is all about encrypting removable media to share with 3rd parties in a secure manner. The 3rd party doesn’t need to install any software, it all runs from the encrypted package, and if its writable media such as a USB device, the 3rd party can even write data back to the device to share securely back with the original DES user. Finally they also have an MSI configuration in the pipeline that I think will help with the installation and distribution of the product, especially in larger enterprises.

For pricing your best of contacting DES yourself, but its my understanding the Home versions are about £45, which just provides secure file encryption (not FDE). Business Desktop licences start at around £75 for small numbers of licences and then decrease in cost as the number of users increases over 1000, and the Enterprise Server is about £250. Maintenance is also available at additional cost as needed.

Picture Montage