Saturday, October 31, 2009

YouSendIt Indictment is a Cloud Warning

IDG is reporting that the former CEO of YouSendIt, Khalid Shaikh, was indicted this week by a grand jury for launching DoS attacks against his former company.

Disgruntled ex-employees sabotaging their old company happens all the time. When that employee is a former CEO or CTO (and Shaikh was both) it makes you wonder what kind of data that person may have had access to. Especially when the company in question is one of the market leaders in so-called managed file transfer.

Managed file transfer companies help people get around limits on the size of email attachments. If you are sending a 2GB file, email is just not an option. Fedexing a DVD is a royal pain and makes you look about as tech-savvy as a government agency that still insists on receiving faxes. This has given rise to a large managed file transfer market, which includes vendors like Accellion, Axway, Globalscape, and many others. There are basically two types of file transfers - the one where your data stays on your servers, and the one where the vendor hosts the data. YouSendIt is in the latter category.

There is something very convenient about externally hosted managed file transfer - you don't have to configure and manage your own server, for starters. But you lose control of your data, and when your provider is breached your data might be exposed. This won't keep you up at night if the only files at risk are photos of your pet cat. But what about companies that use YouSendIt or other cloud services to transfer confidential files?

To be certain, there is absolutely no indication that Shaikh or any one else at YouSendIt accessed any data improperly. The only charges relate to the DoS attacks. But the incident serves as a good example that when your data is in the cloud, you need to be sure that your cloud provider has the right measuers in place to protect against external and internal attacks to their network.

There are not many enterprises that can withstand an attack from a technically sophisticated former insider who is willing to criminally attack the enterprise. After all, this person knows

1) the network and data architecture like the back of their hand
2) security vulnerabilities
3) passwords that haven't changed (and how many companies change all their passwords every time someone leaves?)

This is why the internal data handling policies of cloud providers are critical to the protection of their customer data. The more robust their data structure is, the less likely that an insider can compromise sensitive data.

So how secure is the data on YouSendIt's servers? YouSendIt has a detailed security policy that describes their overall security narrative. Against an insider, the most important security measure is data encryption. But their policy implies that data is not actually encrypted on YouSendIt's servers:

All files stored on YouSendIt servers are encoded and stored using a scrambled name, which makes it impossible for a network intruder to identify the file by its original name or read the contents of the file. In order to access and download a file from YouSendIt’s servers, either the full download link or complete user credentials are required.

I don't really know what "encoded and stored using a scrambled name" means, but I can't imagine it means encryption. After all, if they were actually encrypting, wouldn't they just say that?

So let's assume that there is no actual encryption - not just obfuscation - in place. This means that any employee of YouSendIt can access raw files if they gain access to the right server.

I have written before about how encryption in the internal environment is not always worth the price, particularly for database encryption which can be costly from both a complexity and licensing perspective. Encryption in that case does little to protect the organization against the bad apples in its midst, because those people likely have access to the raw unencrypted data in much easier to reach places. But in the cloud this whole calculus is reversed, which is why encryption of data should be a requirement for any cloud deployment.

I certainly do not mean to pick on YouSendIt. As far as cloud managed file transfer systems go, they at least have a detailed explanation of their security policies on their site. The fact that they are one of the larger companies in this space also provides some reassurance. But the indictment of their former CEO should act a a general wake-up call for anyone who is thinking of using cloud services for confidential information.

In the end, enterprises need to make their own risk assessment for using such cloud based services. For low to medium security files, using a cloud managed file transfer solution does not introduce significant new risk. However for highly sensitive files, incidents like the YouSendIt attack are further evidence that enterprises should either stick with internally hosted solutions, or should use the cloud with caution. Encrypting files prior to using the cloud is one measure that grants additional peace of mind at the cost of slight inconvenience.


  1. Hi Boaz. Great article, you've hit the nail of the head regarding the trade off when using managed services as opposed to an in house solution. Its a topic I'm very interested in as a supplier of secure file transfer solutions and had previously written about on our blog (

    There has in recent times been some significant steps forward in addressing the security of files using internally hosted solutions for enterprises, such as Biscom Delivery Server. Biscom for example secures the data from the desktop to the server and then encrypts the data at rest and provides SSL encyption on download by the recipient. Effectively closing the security loop.

    I'm quite surprised by YouSendIt's lack of encryption of the data but then with the volumes of data traversing their servers the additional load placed on them for this process may have some bearing. You might have a better idea than I regarding that.

    Best regards,
    James Lewis
    Pro2col UK

  2. Thanks for the comment James. Encryption at rest is probably overkill for services that are used to transfer large video files that are either not particularly confidential or are only confidential for a short period of time. So to the extent that YouSendIt is primarily used for such file transfers, there is a valid business argument for not encrypting the data at rest.

    For internally hosted solutions, encryption at rest only marginally improves security at the cost of considerable complexity. The last time I did a detailed evaluation of MFT products, I found that most internally hosted solutions do not encrypt data at rest. This seems to be changing now, probably as a result of regulation and customer demand.


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