SHA-1 for mail, SHA-2 for web

June 10th, 2015 by

SSL Certificates do two things. They encrypt the traffic between the end user and the website, and they provide authentication that confirms the website is who they say they are. As we previously wrote about at present the authentication step is done using a piece of maths called SHA-1.

What the SHA-1 function does, is to provide a signature that says ‘The Certificate Authority confirms that the public key for Mythic Beasts is ….’. It’s extremely important that nobody else can forge this signature, otherwise anybody could present their public key instead of the Mythic Beasts public key and intercept all of the data.

Now SHA-1 has been subject to a lot of analysis by people attempting to forge keys, and slowly progress has been made. SHA-1 has not been “broken”, but thanks to improvements in mathematics and computing, the estimated cost of forging a certificate has steadily fallen from more-money-than-exists to a-large-country-could-do-it and in the next 5 years is likely to reach script-kiddy-with-a-botnet-could-do-it.

So Google, Firefox and others now refuse to accept SHA-1 based certificates that will last into 2017. Whilst you can’t forge them now, in two years time it’s likely that well funded organizations may be able to do so. As a result, the Internet has had to migrate to SHA-2, a new function that achieves the same as SHA-1 for proving authenticity but has no known attacks: forging a SHA-2 signature is currently believed to be entirely infeasible. Google’s announcement of their intention to deprecate SHA-1 was greeted with dismay and anger, but in the end had the desired effect. The certification authorities moved quite quickly to make SHA-2 the default.

At Mythic Beasts this week, we replaced our SSL certificate for all our servers. As expected, the new certificate we were issued was SHA-2 based. Deployment of the new certificate went smoothly, sufficiently smoothly that not a single customer noticed. A short time later we realised that we now didn’t seem to receive any support mail at all.

Our ticket tracking system runs on top of mono, an open source reimplementation of .NET. The older version of mono it uses doesn’t have support for SHA-2 certificates, so our tracker was seeing the secure connection, failing to authenticate and refusing to send or receive email. Briefly we worked around this by turning encryption off for the support system – as the traffic is entirely within our network we aren’t so worried about it being intercepted.

However, we know that our end-users use a wide variety of different clients for email, some of which are quite old and obscure. So we thought it was rather likely that we were breaking email functionality for existing customers with the SHA-2 certificate. We decided the sensible thing to do would be to use the new SHA-2 certificate just for websites, and obtain a new SHA-1 certificate for mail applications.

We will face the same issue again in 12 months. (Except we don’t even know if the certification authority will still offer the choice of getting a SHA-1 certificate then.) We’re hoping that a year will force a number of updates to mail clients and system libraries such that next year we can deploy SHA-2 everywhere. Eventually, we will have to draw a line, and say that if our customers’ clients don’t support SHA-2, they will have to upgrade them, or use unencrypted access.

In a little known fact, here are two old men singing about SSL security beginning with a limited understanding of SHA hashes. It delightfully uses the metaphor of a journey to meet their loved one to show how the process of security is a continuous process that can never be fully achieved.