SMTP Downgrade Attacks and MTA-STS

14 pointsposted 14 hours ago
by 8organicbits

6 Comments

turnsout

31 minutes ago

Is there a recommended setting for Postfix users based on this article?

rswail

7 hours ago

It's irritating (to say the least) that we have a distributed information service (DNS) that so botched its security implementation that logical things like storing public keys now require a web server, running http (!) and allowing a GET on /.well-known/blah

Is there no alternatives to DNSSEC that would have allowed the equivalent of DANE to be provided somehow?

8organicbits

3 hours ago

Blog author here, great question. I think HTTPS was chosen because, as an industry, we have exceptional knowledge of how to securely serve static web content. Some folks are using GitHub Pages for their mta-sts subdomain, for example. It's quite painless to set up and easy to reason about the security it provides.

Using TLS provided by the mail server may have been possible, similar to how the HSTS header is sent over the HTTPS connection. But unfortunately the MTA-STS policy if for the receiving domain (@example.com) and the receiving mail server may be run on a completely different domain. We need a signal that cryptographicly relates to the receiving domain.

rubatuga

3 hours ago

Defaulting to SSL only is the easiest way. I'm surprised the industry has not moved on yet ... my mail server enforces SSL only.

Wicher

an hour ago

Even if you enforce SSL-only on inbound mail, you're still vulnerable to the downgrade attack (or rather: the "prevent upgrade to TLS attack") - someone can MITM, and the sender will be speaking non-SSL to the MITMer, who'll speak SSL to you. To you things would look fine. Enter MTA-STS, with which the sending mail server can deduce that no, things are not OK.

Or are you saying you're not doing STARTLS at all and servers delivering mail to you have to do an SSL handshake before getting to speak SMTP to you? I'm quite surprised if that's compatible with the wider SMTP world.

8organicbits

2 hours ago

That's a hard choice. Google reports that 2% of the email they send goes out unencrypted, it's too large a percent to ignore. If you are using Postfix, would you mind sharing which setting you use? They all have challenges.