A review of the IronKey USB Smartcard + Flash Drive + Anonymizer

Over the last few years there have been a number of new entrants to the USB flash product space that position themselves as “security devices”, these devices typically build on top of their flash heritage by adding encryption software (ala PGP Disk) that is resident on the token, this software is typically invoked via the Windows AutoPlay mechanisms which then mounts a encrypted volume.

 

These solutions are “neat” and all, but they have a number of short-comings, two of the most significant being:

1.       All of the units I have played with up until now do the encryption in software – The problem with this is that the encryption and decryption happens in user space, this means that one can attach a debugger and extract the associated key material; there are techniques that can be applied to make this more difficult but in the end there is no way to prevent such attacks (see Playing hide and seek with stored keys by Shamir and van Someren).

2.       All of the units I have played with up until now require administrative privileges to “provision” a machine they hook into – This is problematic as well since I often want to use a flash drive on guest PCs as a means to share content (like we used to do with floppy disks)  and people do not want you installing software, especially drivers to get a presentation.

 

The other thing about these tokens is they offer insufficient visible value to justify their increased cost, this is often the case with security solutions after all if it’s designed well and working you barley know it’s there.

 

Then there is the business proposition these tokens have, since the encryption is happening in memory the incremental value is pretty limited since an attacker with physical access (which should generally be presumed) can via a number of ways bypass the protections such devices have, for example a software device that offers a “lockout” capability can be modified (via a single hex editor) to never lock out then your down to brute forcing the password using their own software.

 

There is a new class of devices, best represented by the IronKey offering coming to market now that address these gaps as well as try to address the value-proposition problem-set by introducing subscriber functionality that helps make the token increasingly valuable.

 

Let’s look at the current generation of IronKey devices and explore how its different than the other tokens out there.

 

First off IronKey took a page out of the Apple playbook and have packaged this thing up first class, when you look at the package you can see thought was given it has a crisp look, a solid feel, when you open up the box you see the IronKey itself is well protected sitting safely in a foam bed cut to fit the key.

 

Then there is the token itself, its waterproof, made of aluminum with some sort of lacquer coating to keep it looking nice (and it meets MIL-STD-810F), the inside of the device is potted to  help protect against physical attacks, to top things off they have made the device both tamper evident and tamper resistant (how well their mechanisms work here are outside the scope of this review).

 

But what about the first run experience? Well other than the fact you have to acknowledge to Windows AutoPlay request (that is a onetime problem if you acknowledge the risk and tell Windows to always run the IronKey application when the token is inserted) it goes pretty smoothly, you register with their web service (including Human Interface Proofs, and selection of images to aid in Phishing detection in later sessions). The core service offered by the web service is pin recovery and software updates, but the key thing about the first run experience is that once your registered with the service your encrypted volume shows up to Windows and your ready to go.

 

Once the token is setup you have a few features available to you:

·         Onboard instance of FireFox that is configured to use IronKey’s TOR like Anonymizing network for browsing, this also allows you to keep favorites with you on your token.

·         Onboard password manager that is integrated with both IE and Firefox via ad-ins, this unlike the browsers native password cache stores the passwords on the encrypted volume to keep them protected; this is a important problem for home users (who commonly do not have passwords) where systems have to use weak mechanisms to derive a secret to keep a secret.

·         Onboard password generator that can be used to generate STRONG passwords that you can’t remember but the IronKey can for you (see: The Great Debates: Pass Phrases vs. Passwords. Part 1 of 3, The Great Debates: Pass Phrases vs. Passwords. Part 2 of 3, The Great Debates: Pass Phrases vs. Passwords. Part 3 of 3 and Microsoft Security Guru: Jot down your passwords).

·         A smartcard, currently its only used within FireFox (via the supplied PKCS#11 library) to authenticate to the IronKey service; the key here is that each token has a IronKey issued device certificate that can be used to bootstrap stronger trust relationships with others.

 

Features are one thing, but what about “how” they executed on those features? Well I have not done a formal analysis of the token but from discussions with folks at IronKey and some basic observations I think they have done things right, for example:

·         They used a TLS based mechanism to protect the exchange of the pin/password from user mode to the token; thus one can’t simply install a USB bus monitor and see the exchange of the password, in the past I have looked at products that in a similar situation chose to just obscure the exchange using something as basic as a XOR but these guys went the extra mile to use proven “real” security techniques to protect this exchange, this is particularly important when inserting a device like this into a guest PC.

·         As mentioned earlier they have gone out of their way to implement tamper resistant and tamper evident mechanisms into the solution so it’s not simply a crypto-processor; They are even currently in the NIST Implementation Under Test (ITU) Phase for FIPS 140-2 Level 3 certification.

·         It’s actually a high speed USB flash device (high speed 30MBS read, 20MBS write), that’s right you can use the drive for ReadyBoost.

·        Designed with conformance with NIST cryptographic guidelines in mind (Recommendation for Key Management – Part 1: General, Cryptographic Algorithms and Key Sizes for Personal Identity Verification)

·        They built lockout and “file shredder” capabilities into the hardware, unlike their software counterparts an attacker would have difficult time bypassing the lockout mechanisms on this token, if you lock the token out your data is done and the token is a brick and its all done in hardware you can’t just patch a file to get by this protection.

 

Well if after reading all I just said you must think this thing is perfect, well it’s not; that’s not to say the token doesn’t kick proverbial ass (it does IMO) but as a security device striving to in-part be a retail channel play (see: Can you sell strong authentication in the retail channel?) it has accepted the struggle of not becoming a ‘Jack of all trades and a master of none.’, some key concerns:

·         Usability – One of my favorite quotes is “when given a choice most uses will choose consistency over efficiency”, this is particularly important when trying to enter the retail channel (see: More autistic than artistic...); I am not saying that the IronKey offering isn’t usable but if they want this to resonate with consumers (people more like my wife than me) they need to make the software less “geek” friendly and more “human-ready” (I highly consider the use of design shops like Thirtteen23 and frogDesign).

 

There are also some other usability oriented work they could do, for example random generated passwords are great, especially when they are managed by the token but I still want a chance to log into a application or website when I don’t have the token with me for that to be possible I either need to generate my own passwords I can remember or they need to provide a mechanism to generate pronounceable passwords (see FIPS 181).

 

·         So close, yet so far away – The hybrid USB token market is a interesting place you have players like IronKey and GuardID with the smartcard, encrypted volume devices, then there are the traditional flash vendors like Kingston adding hardware encryption to their existing tokens, and then the smartcard vendors like Aladdin are adding flash support to their tokens.

 

I should say that right now I think IronKey is the best overall available offering but that’s some stiff competition, for them to stay on top they need to really innovate in the software they offer so that they can continue to standout as these other solutions are likely to continue to beet IronKey on cost simply because they don’t do as much and ship in larger volumes.

 

·         Is it just too different? – Today consumer electronic devices are starting to use flash drives as a means to do firmware upgrades in the field, this is great as it means it’s now practical to get the latest software on our TVs and home entertainment devices, the downside with devices like the IronKey is that these devices cannot use the encrypted volume and since no clear volume is provided users may end up feeling “burned” that they spent their good money on this token but can’t use it like their lesser expensive cousins.

 

·         Not functional enough? – Although the first version of the IronKey trounces the competition in breadth right now it’s a little short on depth in some areas, the most notable absence is that of CryptoAPI integration; for those not familiar CryptoAPI is the windows platform for Cryptography and Certificates, the token has all of the “right stuff” as it were but the goal of not requiring admin means extending Windows was not possible, they need to find a graceful way to bridge this gap.

 

I also would like to see more consumer oriented functionality maybe integration with WinLogon to enable local logon with the IronKey, maybe a local Windows Single Sign-On functionality that would be able to manage passwords for local applications as well as the current web password manager.

 

There are other possibilities too, like integration with Windows contact manager, maybe roaming user profiles onto the token, integration with the new smartcard root store functionality to carry trust anchors (like the IronKey Browser CA).

 

·         Not secure enough? One of the most significant risks devices like this have is that of pin monitoring (especially on guest systems), the devices use of TLS to protect the passage of the pin from the host PC is great but there is the path between the keyboard and their application that is not protected. Examples include physical key loggers, as well as logical ones.

 

There are a number of techniques that can be applied to mitigate the risks of key loggers, but all of the ones I can think of right now either require a online service to be available at login (e.g., challenge response like systems), administrative privileges and work to get the pin prompt into session 0 (this does not help with physical key loggers or root kits) or hardware changes.

 

·         Can you make these things cool? – Now I am a paranoid security guy, so I personally think these things are cool but sadly (or luckily for the rest of the world) most people are not like me, thus there needs to be something about these that make them “cool” for normal people; since I am as far from a expert on cool as there is I can’t tell you what that is but I strongly believe this will be needed for retail success. On a related note there is a Korean company marketing a graphical password scheme to the masses, the ads clearly are marketed at the young “hip” crowd maybe there is a lesson here.

 

It’s about time I shut up and summarize my experience with the token, I think the IronKey team has done a great job, they have a long road to hoe but they made some good decisions on what to include in their v1 offering as and from my perspective delivered the best available option on the market in for a secure flash device today and as long as they use that platform as the basis for future work and do not orphan the early adopters I think they have a strong chance of success.

Print | posted on Saturday, August 18, 2007 3:05 PM

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# re: A review of the IronKey USB Smartcard + Flash Drive + Anonymizer 8/21/2007 8:39 AM Ryan

There is a neat video/advert on the IronKey here: http://ehbovoorjepc.blogspot.com/2007/08/usb-stick-vernietigt-zichzelf-bij.html


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 re: A review of the IronKey USB Smartcard + Flash Drive + Anonymizer 8/21/2007 11:17 AM Ionia

I've been an avid Ironkey user since I lost my old flash drive with all my spreadsheets on it.
I love the Demo on their site:
https://www.ironkey.com/demo


 re: A review of the IronKey USB Smartcard + Flash Drive + Anonymizer 8/29/2007 6:23 PM Solomon Templekin

This is another device that because it not open source / open hardware, it not really secure (in any authentic use of the word).

It likely contains all sorts of spyware that is mandated by various government agencies (and whatever bonus spyware the company puts in it that gathers information the company thinks it can sell later on).

For example, there is no guarantee that your 'safe surfing' records are not given/sold to various outside agencies.

Additionally, there is no guarantee that all your passwords are safe if you use the online backup (because of alternative access keys and various key escrow rules).

As it says on the IronKey website:

"If required by law, through subpoena or other legal requirement, we will release information in our possession about members that are the subject of an investigation."

The company that succeeds in this space will have THE CUSTOMER's security as their exclusive focus. This is not IronKey with their super vague "other legal requirement".

Maybe the product should have been named "IronCuff".

On the company's financial side, Bill Harris will make sure IronKey gets flipped at the right price to the right buyer. This means that IronKey will sign a few big name customers, get a little more buzz going, and that'll do it. A nice shiny looking product is a good first step.

At the end of the day, this company will amount to a few fat cats getting richer and a dead on the vine product line at some big conglomerate.


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# re: A review of the IronKey USB Smartcard + Flash Drive + Anonymizer 8/30/2007 10:43 AM Ryan

Thanks for posting Solomon; I don’t personally buy into the if it’s not open-source it can’t be secure mind-set (although I am a past contributor to open source projects and consider myself an-advocate); that’s not to say that you’re not entitled to your opinion.

Something that you may not be aware of is that FIPS 140-2 evaluations require you to provide the source for the code within the cryptographic boundary, thus we have a fairly reasonable assurance (once they finalize their evaluation) that the crypto on the device is neither evil or incorrect in its cryptographic implementations.

As for the anonimizer, IronKey claims their solution is a implementation of the well reviewed (and open-source) Tor, Tor uses cryptography to provide perfect forward secrecy for the traffic that goes through its network. Although it is true that a onion router (used in Tor) does have access to the clear text as it exits its interfaces the traffic gets routed through a mix of routers so that no single router can compromise all traffic. IronKey has also gone one step further by configuring private DNS servers to help protect against DNS redirection attacks (I verified this). In the end though if you do not trust IronKey as a company you should not believe their software is in-fact a proper Tor implementation, or that their onion routers have not been modified to collude.

With that being said as a start-up I find it un-likely they have spent the energy to make their Tor implementation “evil” as their goal is surely to make a product they can sell and they should have more business positive priorities; if you do not trust them however you always have the option of using the eff tor network instead (although it would be slower).

That takes us to your claims on their backup service, although their backup logic is not part of the FIPS 140-2 evaluation (thus your source requirement is not met) they claim that they encrypt the backup data with a AES -256 key generated on token, kept in the token before they submit the data to their servers for archival. The key thing about this is that with this design even though they offer a token password recovery mechanism they do not have the ability to decrypt the data, they need your token.

Without a third-party audit, or opening their source I can’t think of any proofs they could offer that they do what they claim here but in this case again it just seems un-likely to me that a company struggling to become relevant would expend energy making the product “evil” when if they want to continue to exist they need to be relevant, the later seems like a more likely place for them to spend their energy.

When it comes to products like this I am more concerned with ignorance (I always liked the quote “Don’t attribute malice when ignorance is a reasonable substitute.”); based on the other design properties the device has and my personal experience with their founder (Dave Jevans) I am optimistic that ignorance is not currently a issue with this product.

On your last points on their business, I would not be surprised if a company as specialized as this gets acquired at some point; it makes sense really, but even if that does happen since the token does not take a hard dependency on the service your data would still be yours, and still be safe (given the assumptions I mention above).

Your post has got me thinking though, I would like to see the IronKey CA undergo a SAS-70 and WebTrust for CA’s audit, it would also be great for them to publish the CAs Certificate Policy Statement as well as a Relying Party Agreement so that its clear what assumptions folks can take on their CA infrastructure.


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 re: A review of the IronKey USB Smartcard + Flash Drive + Anonymizer 11/5/2007 11:38 AM Jason Bing

I agree, Ironkey is very secure, and is a durable, well made piece of equipment. The only problem with it is the price. You can do the same thing for under $40. Check out this article here:

http://www.bauer-power.net/2007/11/seriouslywhy-pay-more.html


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# re: A review of the IronKey USB Smartcard + Flash Drive + Anonymizer 11/5/2007 1:03 PM Ryan

On price your right they are expensive (possibly more so than they should be even).

But comparing the Toshiba referenced in that post (http://www.geeks.com/details.asp?invtid=U2H-004GT&cat=UFL) to the IronKey is an apples to oranges comparison; simply put its nowhere near the device the IronKey is.

Specifically it’s just a plain-old-flash drive, like the one you probably already have that you can put software (freeware) on that gives it some of the same capabilities but it’s all done in software and that’s the rub.

Since its all software crypto its trivial for any other software (malware) running in the same user context of the encryption software to get the keys and decrypt the content; one could argue that the lack of defense from a key logger in the IronKey makes this risk moot but it doesn’t, the thing is a software key logger requires your code to run as root a user mode application could easily be able to attack a software only solution.

There are so many other differences I don't have the time to go over them but Dave apparently has responded to that post with some of the highlights here:
http://www.bauer-power.net/2007/11/rebuttle-from-ironkey.html.

Bauer’s response to Dave seems to focus on claims around the brute force strength of the IronKey and how a sufficiently long and secure password can mitigate that risk; and at the high level there is truth to that statement the devil is as they say in the details; and the practical issue is that people pick crummy passwords even the security “geeks” do, and the use of hardware significantly reduces the risks associated with that habit.

Now I am not saying that using software crypto is a waste, it does mitigate many attacks but a determined attacker could easily bypass the protections of such systems while doing so against a hardware based solution requires a different class of attacker.


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 Independant Security Assessment 11/12/2007 11:13 PM Andrew Probert

I've just heard about the product and certainly the onboard crypto / browser integration gets rid of a myriad of deployment issues.

I'd suggest an appropriate way to assure of anything like this is not SAS70 / Webtrust, but instead with an EAL4+ or EAL5 evaluation. http://en.wikipedia.org/wiki/Evaluation_Assurance_Level

A number of smartcard vendors have gone down this path already, with Visa Open Platform/PKCS#11, Multos open standards, and fixed function PKI / PKCS#15 crypto-chips.

I'll be posting some questions of this type to the discussion group.



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# re: A review of the IronKey USB Smartcard + Flash Drive + Anonymizer 11/15/2007 2:59 PM Ryan

SAS70/WebTrust and FIPS/CC look at totally different things, the SAS70/WebTrust would be relevant to their operational issues while the FIPS/CC evaluations look at the token itself.

The last posters comment was specifically related to the trustworthiness of their private TOR network, see http://www.schneier.com/essay-182.html for information on the topic.

Both evaluations are relevant if you don't trust IronKey; that being said satisfying both or a myriad of others would also not guarantee the privacy the other poster was looking for only a solution with code and operations he personally could review that is operated by individuals he personally trusts would meet his requirements.

FYI they are already undergoing FIPS/CC evaluations (or so I understand, they are listed on the NISY FIPS 140 in progress list).


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# re: A review of the IronKey USB Smartcard + Flash Drive + Anonymizer 11/15/2007 3:01 PM Ryan

SAS70/WebTrust and FIPS/CC look at totally different things, the SAS70/WebTrust would be relevant to their operational issues while the FIPS/CC evaluations look at the token itself.

The last posters comment was specifically related to the trustworthiness of their private TOR network, see http://www.schneier.com/essay-182.html for information on the topic hence the relevence of the operational audits.

Both evaluations are relevant if you don't trust IronKey; that being said satisfying both or a myriad of others would also not guarantee the privacy the other poster was looking for only a solution with code and operations he personally could review that is operated by individuals he personally trusts would meet his requirements.

FYI they are already undergoing FIPS/CC evaluations (or so I understand, they are listed on the NISY FIPS 140 in progress list).

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