The sad state of SMTP encryption
blog.filippo.io
The sad state of SMTP encryption
1–10 of 65 posts
Re: The sad state of SMTP encryption
#2Wow, that's an eye opener. Thanks for the write up.
Re: The sad state of SMTP encryption
#3It seems to me a little biased: CloudFlare post about DNSSEC and now Filippo, who works for CloudFlare.
Re: The sad state of SMTP encryption
#4S/MIME also neatly solves the problem.
Re: The sad state of SMTP encryption
#5In fact (as the article admits), the encryption is fine and fully effective against a passive attacker, the problem is that it's not much use against an active man-in-the-middle. But, that's not something anyone but a NSA or ISP can easily do between mailservers.
Re: The sad state of SMTP encryption
#6Right now I am thinking a HSTS-like solution is the best idea for now, though I do wish for a DNSSEC2 eventually.
Re: The sad state of SMTP encryption
#7In fact (as the article admits), the encryption is fine and fully effective against a passive attacker, the problem is that it's not much use against an active man-in-the-middle. But, that's not something anyone but a NSA or ISP can easily do between mailservers.
The problem is that most of my emails will end up on Gmail, Yahoo! or Hotmail. Since nearly no one uses PGP, the emails sit on a google, apple, yahoo, microsoft server in plain text for any ads or 'gov' company to see and analyze in bulk.
Until we 'solve' THIS problem, there's no point in discussing what happens in between IMHO.
Re: The sad state of SMTP encryption
#8S/MIME also neatly solves the problem.
The problem is not encryption, S/MIME works well enough for that.
The problem is you don't have public keys for people you send to.
And there's not a reason for many to get the keys.
I wish I could say "I'll read your unencrypted email tomorrow" (and delay it from getting to my inbox).
Re: The sad state of SMTP encryption
#9It's indeed not a nice situation, I'd love for my mailserver to insert a line into the message subject something like: 'TLS not used' when this is the case (or a plugin for Roundcube (Next?) that colors the subject, how cool would that be?). Just so I know and are aware of suspicious things. Enforcing TLS (and valid certs + strong encryption) is just not very practical yet, although it will definitely not affect mayor players' connectivity (Google, Apple, MS). Still, a lot of problems will arise, to see how many exactly, this is a rough indicator: http://www.google.com/transparencyreport/saferemail/
I predict in my group of friends I can receive/sent from/to almost everyone if I would enfore TLS on my server. Except to/from that one guy that is savvy enough to have his own domain but hosts his email at a cheap, crappy provider.
Re: The sad state of SMTP encryption
#10In fact (as the article admits), the encryption is fine and fully effective against a passive attacker, the problem is that it's not much use against an active man-in-the-middle. But, that's not something anyone but a NSA or ISP can easily do between mailservers.
If you can see a DNS request going out and can send a fake response that arrives before the real one, you have enough resources to pull off a MITM.