Mail server

Why Hillary Clinton’s Mail Server Is Less Weird Than You Think

People bypass the precautions that IT departments take for them all the time: they forward corporate emails to private addresses on Gmail, Hotmail, or Yahoo! ; they insert untested USB sticks into machines; and they copy files to their own devices. Usually they do this stuff in order to get the job done more efficiently. By running a private mail server, Hillary Clinton was doing a more complex version of the kind of stuff millions of other Americans do.

Calling Clinton’s setup “home brew” sounds like she got someone’s nephew to create untested code that ran on a Raspberry Pi computer. The reality is that she seems to have used vendors well known and reputable. Political points aside, the fact that many call his arrangement home shows how the widespread use of webmail has changed expectations. Just ten years ago, it was not uncommon for those with some technical ability to operate their own mail servers. Now, that’s considered a bit weird, even among geeks who bemoan the privacy-invasive centralization of these services.

I configured my server in 2003 to do three things: consolidate a myriad of historical email addresses; reduce spam; and ensure that I was in control of my most critical communication function. My setup works as well as Gmail or Hotmail, but no one scans my messages for targeted advertising and no one can get the full archive by making a secret deal. Clinton’s motives are unlikely to be the same, but I would expect control to be on her list, especially given her political history. Having its own server also exempts it from changing its address each time its professional status changes. It also keeps him from being at the mercy of mass-market providers who cut and change services to their advantage, not his.

The two main reasons the public are concerned about their decision to use a home mail server rather than one officially run by the State Department are transparency and security.

As a public servant, Clinton is required to ensure that copies of her correspondence enter the historical archives. At least in theory, running a private mail server gives Clinton the power to select which emails she chooses for logging, withholding or permanently deleting the rest. As millions of people can attest, however, you can never be sure that no copy will surface later. A smart government official wishing to keep communications secret would do well to avoid anything electronic. In this case, Clinton’s situation mirrors ours: To what extent should employers – in this case, us – have the right to monitor their employees?

Security is more complex. Email is an inherently insecure medium with many moving parts, each of which can be compromised, attacked, or misconfigured. Encryption is essential to protect messages against interception or tampering, both in transit and at rest. It is increasingly common to configure mail servers to use Transport Layer Security (TLS) to encrypt all incoming and outgoing channels. Although the National Security Agency as well as the UK government’s communications headquarters have apparently compromised TLS, it will still defeat most potential snoopers. A mail server using TLS has a cryptographic code called a certificate, which the mail software and other servers check on every connection to verify the identity of the server. Most servers pay a certificate authority a few hundred dollars for a single certificate; however, many smaller ones sign their own. Experts quoted by Bloomberg report that Clinton’s server used a self-signed certificate that came with the device his server is running on. It’s a vulnerability that sites such as Gawker, Wired and Gizmodo have exposed, noting that the government itself uses much stronger military-grade encryption and certificates. Message-level encryption, which is built into the email client software rather than the servers themselves, is a separate issue. Ideally, you would want the Secretary of State to use it as well. We don’t know if Clinton did it.

All this to protect against two main risks: interception and tampering. For a Secretary of State communicating with high-level diplomats in other countries as well as with her own staff, it is crucial that her messages reach only the intended recipients, but also to be sure that only messages from actually from her were sent. For most of us, the danger that our email has been spoofed ends in embarrassment and perhaps tech support cleaning viruses from our click-loving friends’ computers. For a secretary of state, it could mean upending months of delicate negotiations.

Experts generally agree that even the best efforts will not protect you from serious, persistent and targeted attacks from actors of the size and resources of a nation-state who can, if online attacks fail, send someone break into your home and install a keylogger on your computer. It’s fair to say that Clinton is unlikely to have the technical resources and funding the government has to protect her emails, although she could counter that with the leak in 2011 of 250,000 US diplomatic cables. And we can hope that she saw email as a bad channel for highly sensitive communications. Until we see the official account, it’s hard to guess how outraged we should be.