The Sorry State of E-Mail

As I briefly mentioned last week I’ve been spending time setting up a new e-mail server. For years I’ve been using OS X Server to run my e-mail server because it was easy to setup. But there are a lot of things I dislike about OS X Server. The biggest problem was with the change from 10.6 to 10.7. With that update OS X Server went from being a fairly serious piece of server software that a small business could use to being almost completely broken. Apple slowly improved things in later released of OS X but its server software remains amateur hour. Another thing that I dislike about OS X Server is how unstable it becomes the moment you open a config file and make some manual changes. The graphical tool really doesn’t like that but it also don’t give you the options necessary to fine tune your security settings.

My e-mail server has grown up and now runs on CentOS. I’ve tried to tighten up security as much as possible but I’ve quickly learned how sorry of a state e-mail is in. One of my goals was to disable broken Transport Layer Security (TLS) settings. However this presents a sizable problem because there are a lot of improperly configured e-mail servers out there. Unlike web servers where you can usually safely assume clients will be able to establish a connection with a sever using properly configured TLS no such assumptions can be made with e-mail servers. Some e-mail servers don’t support any version of TLS or Secure Socket Layer (SSL) and those that do often have invalid (expired, self-signed, etc.) certificates. In other words you can’t disable unsecured connections without being unable to communicate with a large number of e-mail servers out there. Let me just say that as much as I hate how everybody uses Google because it makes the government’s surveillance apparatus cheaper to implement I appreciate that the company actually has properly configured e-mail servers.

Another problem with securing e-mail servers is that they rely on the STARTTLS protocol. I say this is a problem because the first part of establishing a secure connection via STARTTLS is asking the server if it supports it through an unsecured connection. This has allowed certain unscrupulous Internet service providers (ISPs) to intercept and edit out the mention of STARTTLS support from a server’s reply, which causes the client to revert to an unsecured connection for the entire communication. This wouldn’t be a problem if we could safely assume all e-mail servers support TLS because then you could configure servers to only use TLS.

What’s the answer? Ultimately I would say it is to move away from e-mail as we currently know it. But that’s easier said than done so I will continue to strong urge people to utilize Pretty Good Privacy (PGP) to encrypt and sign their e-mails. Even if a PGP encrypted e-mail is transmitted over an unsecured connection the amount of data a snoop can collect on you is far less (but since PGP can only really encrypt the contents of the e-mail a great deal of metadata is still available to anybody observing the communication between e-mail servers).

I also urge people to learn how to setup their own e-mail servers and to do it. Ars Technica and Sealed Abstract have good guides on how to setup a pretty secure e-mail server. However there is the problem that many ISPs block the ports used by e-mail server on their residential packages. So implementing an e-mail server out of your home could require getting a business account (as well as a static Internet protocol (IP) address). A slightly less optimal (because your e-mail won’t be stored on a system you physically control) option of setting up your e-mail server on a third-party host is a way to bypass this problem. Unless people stop relying on improperly configured e-mail servers there isn’t a lot of hope for salvaging e-mail as a form of secure communication (this should give people involved in professions that require confidentiality, such as lawyers, a great deal of concern).

Many people will probably become discouraged after reading this post and tell themselves that securing themselves is impossible. That’s not what you should take away from this post. What you should take away from this post is that the problem requires us to roll up our sleeves, further our knowledge, and fix it ourselves. Securing e-mail isn’t hopeless, it just requires us to actually do something about it. For my part I am willing to answer questions you have regarding setting up an e-mail server. Admittedly I won’t know the answer to every question but I will do my best to provide you with the knowledge you need to secure yourself.

3 thoughts on “The Sorry State of E-Mail”

  1. I know it is not an Optimal setup but simply using something like Thunderbird with a PGP plugin and pulling your Email off of a public Email server like goggle is better than most and google has no problems ferrying your encrypted traffic along with everything else. Plus when you have it set to delete email from the server when it accesses it there are not emails left for the Feds to say have been abandoned.

    1. The question when it comes to deleting e-mails on a third-party server is whether or not they get purged from backups. Since it’s impossible to verify e-mails you’ve deleted are removed from backups you left having to assume they’re still there for feds to obtain.

      But I will repeat that Google actually has properly configured e-mail servers that utilize modern cipher suits and TLSv1.2 if the server being connected to supports them. That’s a huge plus right there.

  2. Yes but you at least get the flimsy legal protection of the mail not being considered abandoned, which is supposed to force the use of a warrant. That and anything I don’t want anyone else to see is going to be encrypted anyways.

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