Email encryption

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The last time I seriously took a look at email encryption was at my old job, using GroupWise 5.5. I did some poking around here with Exchange/Outlook and made it work, but it wasn't a serious look. Back then there was still real doubt about which standard would reign supreme: PGP (or GPG) vs S/MIME. PGP had been around for ages, where S/MIME used the same PKI infrastructure used by banks for secure online banking.

Outlook and GroupWise both had S/MIME built in. Both used the Microsoft crypto API. Remember, this was GW 5.5 so there was no Linux version yet.

If you look at posts on Bugtraq, clearly PGP is reigning supreme. A lot of posts there tend to be signed, and almost all of the signatures are GPG (the GnuPGP) or PGP. So that would tend to suggest that PGP-style stuff is winning. Except... bugtraq is primarily a Linux list that also bashes Microsoft, so the preference for the old school secure email (PGP) is easy to understand.

Yet why are the major email systems shipping with S/MIME built in?

There are several reasons why digitally signed email hasn't caught on. First and foremost it requires active use on the part of the user, in the form of explicitly stating "I trust this user and their certificate". Second, managing certificate renewals and changes adds work. Third, certificates for S/MIME are subject to the same SSL problems web-site certificates are, price. Fourth, the certificates (be it PGP or S/MIME) generally are only usable on a single operating system instance, which makes portability challenging. still offers free email SSL certificates for personal use. I haven't read the details, but I suspect that 'professional use' is invalidated, which would prevent WWU from going to them whole-sale. I'll have to look.

The very nature of secure email makes it something only people who want it will strive for. This is not something that can be pushed down from On High unto the masses for enterprise deployment. Like sites with bad SSL certificates, Outlook will throw a Warning! message when it receives an email signed by a certificate it doesn't trust or know about. End users are notorious for being annoyed by pop-ups they view as superfluous. As with SSL certificates we have the Trusted Certificate Authority problem, which means that any external signed communication needs to be signed with a certificate already known by everyone (i.e. VeriSign, or similar).

And ALL of this doesn't look at the problem of digitally signed email in web clients like gmail. I have many friends who use their web browser as their primary email interface. AJAX can do a lot, but I don't know if it can do secure decryption/validation of email. I'm pretty sure AJAX can do insecure decryption/validation, which sort of violates the point. Right now, in order to do actual secure email you have to use a full mail client with support for the relevant protocol(s). Which means that, as above, only people serious about email security will take the steps to do email securely; it can't be mandated and invisible to the user.

So, things haven't changed much in the 4-5 years since I last looked at it.

Portability could be solved through creative use of a directory-service. I know for sure that eDir can store SSL certificates just peachy, the trick is getting them out and integrated into a mail client by way of LDAP. Active Directory has similar capabilities, but even Microsoft hasn't implemented AD/SMIME integration.

That said, directory integration provides its own problems. I, with my god like powers, can create and export private keys for generic users and through that securely impersonate them. This creates a non-repudiation problem, and is the reason that Microsoft's SecureAPI has a setting to require a password to be entered before using a certificate for signing. That password is currently set on the local machine, not in AD, which is how god-like-me can be foiled in my quest to forge emails.

Still, email security remains the purview of those to whom it is important. Lawyers and security professionals are the groups I run into most often that use it. I know some hobbyists that use the technology between themselves, but that's all it is, a way to prove that they can make the technology work in the first place. It still isn't ready for "the masses".

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Regarding GPG, restek is a big fan. Most of the devs use it on a daily basis with Thunderbird+Enigmail. Yes, we are known for being open-source friendly.After using it for a while, I cringe whenever I see credentials sent in plain-text. If there's anything the recent MediaDefender email leak teaches us, it's that email is a huge attack surface; especially when email forwarding and unencrypted webmail are so common. I know there's a firefox extension out there that will sign/encrypt any-old text. I'm assuming it's relatively secure.