Protocol-relative URLs in email

When you link to an external resource – an image, a javascript file, some css style – from a web page you do so with a URL, usually something like “https://example.com/blahblah.css” or “http://example.com/blahblah.css”.
The world is beginning to go all https, all the time, but until recently good practice was to make a web page available via both http and https.
The problem is that if you try and load a resource from an http URL from a page that was loaded via https it’ll complain about it, and not load the resource.
And if your users web browser is loading the http version of your page because it’s Internet Explorer 6 and doesn’t speak modern SSL then it’ll be unable to load anything over https, including any of your resources.
So whether you choose https or http protocol for loading your page resources it’s going to break for someone.
One common trick to avoid the problem is to use a protocol-relative URL. That looks like “//example.com/blahblah.css”, and it’ll load the resource over the same protocol that the page was loaded over.
While we can safely use “https://…” everywhere now, “//…” URLs are still a common idiom for things like loading things like CSS libraries from public content-distribution networks as well as your own resources.
I was reading long-but-excellent writeup about Stack Overflow’s migration to TLS (hey, I read this sort of stuff for fun) and they point out something I hadn’t considered – mail clients don’t really have any sensible way to use protocol-relative URLs. The mail client loaded the “page” from a mailbox and so has no base document protocol to work from (even if there’s a <base> element in the content it’s not likely to affect a mail client). If the user is reading it via webmail or a mail client that’s using an embedded web browser to render HTML it might work, sometimes, but it’s not going to reliably load that resource in general.
So, if you’re copy-pasting content from your web collateral to reuse in an email, make sure you’re not loading anything external – including images – via a “//…” style URL. Rewrite them to use “https://…”.
 

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Yesterday Gmail announced on their blog they would be pushing out some new UI to users to show the authentication and encryption status of email. They are trying to make email safer.
There are a number of blog posts on WttW for background and more information.

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Protect your email with TLS

You probably use TLS hundreds of times a day. If you don’t recognize the term, you might know it better by it’s older name, SSL.
TLS is what protects your data in transit whenever you go to Google, or Yahoo or even this blog. The little padlock in your browser address bar tells you that your browser has used the TLS protocol to do two things. First, it’s decided that the server you’re connecting to really is operated by Google, or Yahoo or us – you’re (probably) not having your session intercepted by someone in the middle between you and the webserver, either to read your traffic or modify it en-route. Second, it is encrypting all the traffic between you and the webserver, so that it can’t be passively monitored while in transit. Because of concerns about ubiquitous surveillance many websites – including ours – are moving to use TLS for everything, not just for protecting a login page or a credit card number.
That’s great for the web, but how does it apply to email? One place it’s used is for connections between your mail client and your local mailserver – sending mail to the smarthost via [rfc 4409]SUBMIT[/rfc] and fetching mail using [rfc 2595]IMAP or POP3[/rfc] almost always use TLS. That protects the privacy of your messages between you and your ISP and also protects the username and password you use to authenticate with.
Mail traveling between ISPs didn’t used to be encrypted “on the wire” , but about 15 years ago [rfc 3207]an extension to SMTP was proposed[/rfc] that would allow ISPs to negotiate during each session whether they should encrypt it or not. This extension, often referred to as STARTTLS after the command it uses, allows gradual rollout of encryption of mail traffic between ISPs without requiring any sort of flag day. A mailserver that supports STARTTLS will tell everyone who connects to it “Hey! I support STARTTLS!”. When a smarthost that also supports it connects to that mailserver it will go “Great! I support STARTTLS too! Lets do this!” and convert the plain text SMTP session into an encrypted session protected by TLS.
Fifteen years seems like a long period in Internet time, but non-intrusive protocol changes can take a long time to deploy. Facebook Engineering have done the work to see how that deployment is going with their survey of the current state of SMTP STARTTLS deployment. The results are really quite positive – over three quarters of the mailservers they sent mail to supported STARTTLS, covering nearly 60% of their users. That’s definitely enough to make supporting STARTTLS worthwhile.
More about TLS and encryption tomorrow.

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Cryptography and Email

A decade or so ago it was fairly rare for cryptography and email technology to intersect – there was S/MIME (which I’ve seen described as having “more implementations than users”) and PGP, which was mostly known for adding inscrutable blocks of text to mail and for some interesting political fallout, but not much else.
pgp
That’s changing, though. Authentication and privacy have been the focus of much of the development around email for the past few years, and cryptography, specifically public-key cryptography, is the tool of choice.
DKIM uses public-key cryptography to let the author (or their ESP, or anyone else) attach their identity to the message in a way that’s almost impossible to forge. That lets the recipient make informed decisions about whether to deliver the email or not.
DKIM relies on DNS to distribute it’s public keys, so if you can interfere with DNS, you can compromise DKIM. More than that, if you can compromise DNS you can break many security processes – interfering with DNS is an early part of many attacks. DNSSEC (Domain Name System Security Extensions) lets you be more confident that the results you get back from a DNS query are valid. It’s all based on public-key cryptography. It’s taken a long time to deploy, but is gaining steam.
TLS has escaped from the web, and is used in several places in email. For end users it protects their email (and their passwords) as they send mail via their smarthost or fetch it from their IMAP server. More recently, though, it’s begun to be used “opportunistically” to protect mail as it travels between servers – more than half of the mail gmail sees is protected in transit. Again, public-key cryptography. Perhaps you don’t care about the privacy of the mail you’re sending, but the recipient ISP may. Google already give better search ranking for web pages served over TLS – I wouldn’t be surprised if they started to give preferential treatment to email delivered via TLS.
The IETF is beginning to discuss end-to-end encryption of mail, to protect mail against interception and traffic analysis. I’m not sure exactly where it’s going to end up, but I’m sure the end product will be cobbled together using, yes, public-key cryptography. There are existing approaches that work, such as S/MIME and PGP, but they’re fairly user-hostile. Attempts to package them in a more user-friendly manner have mostly failed so far, sometimes spectacularly. (Hushmail sacrificed end-to-end security for user convenience, while Lavabit had similar problems and poor legal advice).
Not directly email-related, but after the flurry of ESP client account breaches a lot of people got very interested in two-factor authentication for their users. TOTP (Time-Based One-Time Passwords) – as implemented by SecureID and Google Authenticator, amongst many others – is the most commonly used method. It’s based on public-key cryptography. (And it’s reasonably easy to integrate into services you offer).
Lots of the other internet infrastructure you’re relying on (BGP, syn cookies, VPNs, IPsec, https, anything where the manual mentions “certificate” or “key” …) rely on cryptography to work reliably. Knowing a little about how cryptography works can help you understand all of this infrastructure and avoid problems with it. If you’re already a cryptography ninja none of this will be a surprise – but if you’re not, I’m going to try and explain some of the concepts tomorrow.

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