As regular readers will know, I’m not a fan of STARTTLS but today I realised that some people are confused as to what it even means. And there’s a perfectly good reason for this – some graphical email software is actually listing STARTTLS as a protocol for talking to mail servers and people are jumping to conclusions.
So what is STARTTLS all about if you go back to basics?
Originally, when only nice people had access to computers, network traffic was unencrypted. If you had physical access to the network you could pretty much read anything you wanted to, as everything connected to the same network saw the same data. This isn’t true now, but encryption you data is a good idea just in case it can be intercepted – and if it’s going over the Internet that’s definitely the case.
In the mid 1990s, the original mass-market web browser, Netscape, decided to do something about it and they (or more specifically their chief scientist Taher Elgamal, invented a protocol called Secure Sockets Layer (SSL) to protect HTTP (web) traffic. Actually, several times as the first couple of attempts weren’t very secure at all.
SSL didn’t really fit in with the OSI model; it runs on top of the transport protocol (usually TCP) but under the presentation layer, which would logically handle encryption but doesn’t usually. To use it you need an SSL layer added to the stack to transparently do the deed on a particular port.
But, as a solution to the encryption problem, SSL took off and pretty much every major protocol has an SSL port along with its original cleartext one. So clear HTTP is on port 80, HTTPS is on port 443. Clear POP3 is on port 110, encrypted on 995. Clear IMAP is on port 143, encrypted on 993.
As is the way of genius ideas in cybersecurity, even the third version of SSL was found to be full of holes. SSL version 3.1, which was renamed TLS, continued plugging the leaks and by TLS 1.2 it’s considered pretty much secure now. TLS 1.3, which interoperates with TLS 1.2, simply deprecates certain cyphers and hashes on the suspicion they might be insecure; although anyone into cybersecurity should tell you that everything is secure only until it’s broken.
Unfortunately, because different levels of TLS use different cyphers and reject others, TLS levels are by no means interoperable. And neither is it the case that a newer version is more secure; bugs have been introduced and later fixed. This’d be fine if everything and everyone used the same version of TLS, but in the real world this isn’t practical – old hardware, in particular, bakes in old versions of SSL or TLS and if you decided to deprecate older cyphers and not work with them, you loose the ability to talk to your hardware.
But apart from this, things were going along pretty well; and then someone had the bright idea of operating encrypted and unencrypted connections on the same port by hacking it at the application layer instead. This was achieved by modifying the application protocol to include a STARTTLS command. If this is received, the application then negotiates a TLS connection. If the receiving host didn’t understand what STARTTLS meant it’d send back and error, and things could continue unencrypted.
In other words, if you’re implementing an SMTP server with STARTTLS, this keyword is added to the protocol and the SMTP server does something about it when it sees it.
What could go wrong?
Well quite a lot of things, actually. Because TLS doesn’t fit in to the OSI model, it’s actually very difficult to deal with the situation where a TLS connection is requested and agreed to but the TLS layer fails to agree on a cypher with an older or newer version on the other end. There’s no mechanism for passing this to the application to say “okay, let’s revert to Plan A”, and the connection tends to hang.
There’s also a problem with name-based virtual servers must all use the same host certificate because the TLS connection must be established before the application layer headers are transferred.
But perhaps my biggest gripe is that enabling STARTTLS makes encryption optional. You’re not enforcing encryption when you need to, and even if you think you are, STARTTLS connection are obviously vulnerable to a man-in-the-middle attack. You have no idea how many times TLS has been turned on and off between the two endpoints.
You might be tempted to think that optional encryption is better than none at all, but in reality it means you don’t care – and if you don’t care, don’t bother. It just leads to a false sense of security. And it can lead to interoperability problems. My advice is to use “always TLS” ports for sensitive data and turn off the old port.
