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How Widespread is Secure SMTP Usage?
Honest Postmaster asks: "Maybe I am a paranoid nut, or maybe I just feel like my users email is as sacred as snail mail (which we like to hope is untouched); but i have been getting a sinking feeling about all the news I have been hearing about NSA & Government agencies getting potential carte-blanch to sniff email traffic (if they didn't have such, already). I did a quick search and found RFC 2487, which seems to define secure transfer of traffic between SMTP servers using TLS/SSL. Firstly, is this truly a reasonably 'secure' solution? Secondly it seems to have actual implementations (e.g. exim), but it will only work if both client and server support it -- how widespread is its usage? is it hopeless to expect every ISP, megamail .com to get around to turning this feature on, or will sniffing just be a part of our everyday reality?"
If you want security, you'll have to do it yourself, I think.
This means, use PGP and don't rely on the SSL/TLS security of your mail server.
The simple fact is that, unless you are dealing with money, it's too much trouble to properly set up TLS/SSL for a server.
And yes, both ends need to support encryption for it to work.
I mean, most websites do not use TLS/SSL, so why should most mail servers?
Gentoo Sucks
I normally hate that new age nonsense, but this is a case where it makes sense.
Don't worry about how many other sites support this, just worry about whether *you* support it. If you're sending sensitive material, you need to use an end-to-end protocol (e.g., PGP) regardless. If you're just trying to do opportunistic encryption of the channel (something which is still worthwhile to minimize the damage caused by casual sniffers), the limiting factor will always be the other side if you make sure that you're ready. If it's a site you often trade mail with, you can always encourage them to enable encryption themselves.
It makes no sense to wait for some magic threshold to be reached since that's the way (if everyone did it) to ensure that nobody acts.
For what it's worth, my outbound mail is qmail with the TLS patch. I hope stuff is encrypted, but if I'm worried I still use PGP. (My inbound mail is handled by my ISP, so I can't control encryption there. I grab mail from it via a SSH tunnel.)
For every complex problem there is an answer that is clear, simple, and wrong. -- H L Mencken
The second and third point here I think are most important. Having just set up a ssl/tls mail server running qmail-ldap.
It comforts me to know remote users/roaming users don't have their passwords floating around plaintext.
It's also very easy for a box in promisc can grab any email on the segment that someone can wedge one in legit or other wise.
There has been a lot of talk that PGP is the only unbreakable encryption method out there
Which is complete bullshit, for 2 reasons:
1) PGP, like virtually any other form of cryptography, is breakable. It may not be breakable in a reasonable amount of time, but it is certainly breakable. Do not use "unbreakable" unless something is, in fact, unbreakable (within whatever environmentt you're placing it).
2) Why would PGP be particularly strong over other protocols? It's not. Hell, it doesn't even include MACs in the messages, which brings up all kinds of problems.
maybe because the RSA has finally found a way to break the PGP encryption?
Umm... wait, what? Perhaps you meant the NSA???
Anyway, maybe it was because they realized that they didn't have any kind of proof that PRZ had exported the code, that if they pursued it with criminal charges, more likely than not the unconstitutional restrictions on crypto would have been declared as such and lifted, and PGP was already widely available outside the US so they weren't getting much out of it.
It's standard practice that once you know how to break someone's code, you don't ever let them know which guarantees that you can keep on reading all their transmissions.
Wait... huh? From what I can get out of this, it would imply that the NSA even if the NSA could break the algorithms in PGP, they would keep up bothering Phil forever, to give people the impression that PGP was still a big threat to them.