Clintonemail & Shadow IT

Note: The information in this post is from the Wikipedia article.

The Clinton email scandal is an interesting shadow IT failure. Based on the Wikipedia article, the domain and mail server were setup in 2008 at a residence before moving to a data center in 2013 for management.

In this situation, we have a user that wants mobile device access on her BlackBerry. I was a BlackBerry Enterprise Admin at that time. At that point in my career, I had advocated and implemented a mandatory password policy and a mandatory device encryption policy on BlackBerry devices for a global enterprise. I’d also implemented device health / status monitoring using the BlackBerry monitoring. BlackBerry also offered remote wipe capabilities that mostly worked. She was asking for the most secure device at that time. She wasn’t asking for an iPhone 1 nor an initial Android. She went rogue and setup her own mail server. I’m going to guess her setup didn’t include a BlackBerry Enterprise Server. IT just said no, the user went rogue.

There should be a history of security incidents / reports around this mail server usage. Why didn’t the security monitoring team notice anything? From a mail flow perspective, this should have stood out as odd. I’m assuming this would have been a relatively high volume external domain. Why didn’t the DLP team notice anything? There should have at least been alerts for classified information leaving the network. Why didn’t audit / compliance catch this? They should have caught the mail filter exemptions that surely existed.

Unless they all did and the reports were buried…

The final wrinkle in the story for me is she eventually moved the server to a cloud provider. Their website mentions they provide managed security services. What are their security practices like? Could any of their employees see her data? Did the investigation include reviewing data handling practices at this organization?


As a followup, I listened to the entire testimony via the Lawfare Podcast. Per the testimony, James Comey indicated the content on her mail server was improperly marked. A properly marked document should have a header and a footer. How did the DLP solution allow an improperly marked document leave the network? Shouldn’t it have flagged the document as being non-compliant?