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This is often explained in a needlessly confusing way.

STARTTLS isn't a problem, the problem is if a user checks a box (or moral equivalent) saying it's optional obviously bad guys will opt for "No". If your client is set to _require_ STARTTLS, then an adversary blocking STARTTLS has the same effect as if they just blocked the IP address of the mail server, you get an error and it doesn't work.

There's no reason to use "opportunistic" STARTTLS for your own mail servers (ie IMAP or SMTP to an outbound relay). Nobody should be configuring their own gear, or corporate gear, to just let somebody else decide whether it uses encryption.

Opportunistic encryption still has a place in server-to-server SMTP relaying, but if you're choosing options like "if available" in a desktop/phone mail client that's wrong.




It may be better than nothing, but it's far from a sure thing: If you can BGP announce an IP, you can get a certificate from letsencrypt.

This is a trivial attack vector not just for state-actors, but also stupid kids: in the early 2000s, I announced Microsoft's AS from my own network (AS21863) to see what would happen and got a significant amount of microsoft.com's traffic. There was no security, and there still isn't: Most multihomed sites that change links frequently inevitably find themselves unfiltered either through accident or misplaced trust.

For this reason, TLS without key-pinning (even with IP filtering, as is popular with a lot of banks/enterprise) is far less secure than people realise, and on unattended links (server-to-server relaying) it offers only some casual confidentiality (since detection is unlikely) at best.

If you use MTA-STS, you have a good chance of detecting this kind of attack though. I've not seen anyone use a long policy on a distant but popular network to require someone BGP hijack two big networks to beat it, but I suspect such a disruption would be felt across the Internet.


Letsencrypt supposedly has deployed a system that makes the connections from different locations around the world to make this attack more difficult and also you can’t get a letsencrypt certificate for gmail.com or microsoft.com (or Gmail.* or microsoft.* for that matter), there’s a block list for high value targets.


I would hope letsencrypt has a number of heuristic safeguards, but I can guarantee they do not make connections from multiple routing paths: My ad server registers a certificate during the SNI hello (but before the certificate is presented), and I get a certificate after a single ping.




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