You don't mind that my mail goes to Gmail, right?

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The NYT reports that a lot of users forward their corporate e-mail to external Webmail accounts:
A growing number of Internet-literate workers are forwarding their office e-mail to free Web-accessible personal accounts offered by Google, Yahoo and other companies. Their employers, who envision corporate secrets leaking through the back door of otherwise well-protected computer networks, are not pleased.

...

Corporate networks, which typically have several layers of defenses against hackers, can require special software and multiple passwords for access. Some companies use systems that give employees a security code that changes every 60 seconds; this must be read from the display screen of a small card and typed quickly.

That is too much for some employees, especially when their computers can store the passwords for their Web-based mail, allowing them to get right down to business.

I'm sure annoying authentication schemes are part of the problem—though most of the organizations I know about only require you to use your SecureID card to make a VPN connection. Not that that's not annoying enough...

In my experience, the problem isn't security but rather usability. Probably the most important factor is remote access. People want to read their e-mail on their Blackberries and the companies often haven't been that good about installing the connecting software that the employees would need to do that. So, the employees install their own connectors on their desktop. Actually, remote access in general is a problem. Webmail is super-convenient and lots of companies don't or won't offer it. But you can help yourself by just forwarding your e-mail to Gmail.

Finally, there's the usability issue. Many enterprises run Exchange and expect their employees to use the matching MS e-mail clients. The reports I've heard from people who've tried are not exactly encouraging. On the other hand, Gmail's interface is actually pretty good, and you can also use Gmail with more or less any e-mail client of your choice.

Lawyers in particular wring their hands over employees using outside e-mail services. They encourage companies to keep messages for as long as necessary and then erase them to keep them out of the reach of legal foes. Companies have no control over the life span of e-mail messages in employees Web accounts.
This is absolutely a real concern, but it's a mistake to focus on e-mail here. It's actually incredibly difficult to avoid creating archival copies of sensitive information. First, many (most?) e-mail systems make copies to the local disk to enable offline work. At this point, it tends to end up in scheduled backups. Even if you manage to suppress this by forcing everyone to work offline or implementing local expire, employees routinely save data to disk and then it gets backed up onto permanent backups. Creating access control and retention policies that stick with the data through this kind of transformation is nigh-impossible with any operating system in common use (there's a close relationship between this problem and multi-level security, by the way). And this is if you control the systems people use. It's of course massively harder when you don't.1

"If employees are just forwarding to their Web e-mail, we have no way to know what they are doing on the other end," said Joe Fantuzzi, chief executive of the information security firm Workshare. "They could do anything they want. They could be giving secrets to the K.G.B."
OK, but this doesn't make any sense. First, if your employees want to give your secrets to the KGB , what they need isn't e-mail, it's a time machine. Second, if they want to give out your secrets, they're not going to forward them to Gmail, they'll bring a flash drive to work and copy all their data onto it. It makes some sense to be concerned about inadvertant information disclosure by employees, but once you assume that you're in an adversarial relationship then you've pretty much lost.

Paul Kocher, president of the security firm Cryptography Research, said the real issue for companies was trust. "If you can't trust employees enough to use services like Gmail, they probably shouldn't be working for you," he said.

I certainly agree that if you can't trust your employees not to intentionally give out your confidential information you're in big trouble, but I don't think it's right to extend this to whether you can trust them to comply with all your corporate IT policies. Just from reading this article (and from my personal experience) it's clear that if you followed that policy you'd have to fire a lot of your employees, including good ones—people who are at least to some extent trying to act in the best interests of the company by working more efficiently.

At a higher level, the relationship between corporate IT departments and individual users is often quite adversarial. The IT departments want to standardize everyone on a particular set of software and services and the users want to use software and services of their choice. When the official IT offerings become too restrictive (in the minds of the users) they often resort to self-help, as in this case.

1. There was some interest for a while in using various kinds of cryptographic techniques for this, but it never really took off and was still hard to get right.

2 Comments

Where I am, people tend to forward to Gmail so that they can take advantage of it's reasonably decent spam filtering since our in-house filters are incredibly lame.

Another reason I've heard about is too small a quota in the corporate account.

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