4 ms·

Why is mail so broken? We send so much confidential information over email, yet have no reliable way to secure the information. We insist on https, so why are w

by josho 12y ago

Why is mail so broken? We send so much confidential information over email, yet have no reliable way to secure the information. We insist on https, so why are we ok with the current lame security around mail? Folks go out and get S/MIME setup, it's not ideal, but a start at least.

atmosx 12y ago
I'm no expert but it's most likely that like FTP, SMTP was NOT designed for the internet. It was designed for LANs or MANs. Security was not one of the core features. Same goes with many old protocols... But that's expected the drama is when new protocols are designed with the same flaws.
- josho 12y ago
  Yup, I get that. Same can be said of http--so we solved that problem and created https. I just don't get why folks like IBM, Microsoft, et al never bothered to push secure email standards. I'm surprised their customers never pushed them to do it. SMTP with starttls is not secure because as an end user I have no idea if my mail is getting sent securely.
  - throwawayaway 12y ago
    You have to go back to the export controls thing in the nineties to understand that: http://www.ussrback.com/crypto/nsa/lotus.notes.nsa.backdoor.txt http://www.ussrback.com/crypto/nsa/lotus.notes.nsa.backdoor....
dredmorbius 12y ago
There were people thinking about security in the 1970s, but the proposals were quashed. A comment from this past August from Karl Auerbach, who was there: I worked on TCP/IP security systems back in the 1970's. In fact one of the threads that led to IP being peeled off from the then monolithic TCP was done on my blackboard at SDC in 1974. The reason we did that was to insert a security/encryption protocol over the packet layer - if it sounds like DNSSEC it should. But in 1974. But it was on a project done for "the government" so it never saw the public light of day. And: We made a huge mistake back in the 1970s when we failed to require a mandatory packet security layer between IP and the protocols over it. (We knew even then that we needed it - and had existence proofs of running code - but the gov't wouldn't let those who knew out into the wild to evangelize the concept. So in some sense the problem we have today is do to excessive closure by certain governmental authorities. Even today I am not at all sure what I can say about this stuff. (He's still under some security prohbitions). https://plus.google.com/106435630686948313794/posts/i4KmivYfXrN https://plus.google.com/106435630686948313794/posts/i4KmivYf...
6d0debc071 12y ago
> We insist on https, so why are we ok with the current lame security around mail? Think how many points you have to change if you want your email to be encrypted among your list of common correspondents vs if a website wants to support HTTPs. You have to change a lot more in one go for email to be secure than you do for a given website.
- josho 12y ago
  Yup, it's going to be hard--lets just not bother. I get it, you've got to update SMTP, the mail client, and likely other points (mail storage). But that's no reason not to try. Look at DKIM and SPF--we've maid steps to protect against forgeries.
  - 6d0debc071 12y ago
    I'm not advocating either way, I'm just saying that it's a problem with a higher barrier to clear since it requires far more buy-in to be meaningfully implemented. You can go and encrypt your email right now but unless you get an organisation with an incredible degree of power to back you you'll be sending messages most people can't read and recieving unencrypted stuff in return.

by josho 12y ago

atmosx 12y ago

I'm no expert but it's most likely that like FTP, SMTP was NOT designed for the internet. It was designed for LANs or MANs. Security was not one of the core features. Same goes with many old protocols... But that's expected the drama is when new protocols are designed with the same flaws.

josho 12y ago
Yup, I get that. Same can be said of http--so we solved that problem and created https. I just don't get why folks like IBM, Microsoft, et al never bothered to push secure email standards. I'm surprised their customers never pushed them to do it. SMTP with starttls is not secure because as an end user I have no idea if my mail is getting sent securely.
- throwawayaway 12y ago
  You have to go back to the export controls thing in the nineties to understand that: http://www.ussrback.com/crypto/nsa/lotus.notes.nsa.backdoor.txt http://www.ussrback.com/crypto/nsa/lotus.notes.nsa.backdoor....

dredmorbius 12y ago

There were people thinking about security in the 1970s, but the proposals were quashed. A comment from this past August from Karl Auerbach, who was there: I worked on TCP/IP security systems back in the 1970's. In fact one of the threads that led to IP being peeled off from the then monolithic TCP was done on my blackboard at SDC in 1974. The reason we did that was to insert a security/encryption protocol over the packet layer - if it sounds like DNSSEC it should. But in 1974. But it was on a project done for "the government" so it never saw the public light of day. And: We made a huge mistake back in the 1970s when we failed to require a mandatory packet security layer between IP and the protocols over it. (We knew even then that we needed it - and had existence proofs of running code - but the gov't wouldn't let those who knew out into the wild to evangelize the concept. So in some sense the problem we have today is do to excessive closure by certain governmental authorities. Even today I am not at all sure what I can say about this stuff. (He's still under some security prohbitions). https://plus.google.com/106435630686948313794/posts/i4KmivYfXrN https://plus.google.com/106435630686948313794/posts/i4KmivYf...

6d0debc071 12y ago

> We insist on https, so why are we ok with the current lame security around mail? Think how many points you have to change if you want your email to be encrypted among your list of common correspondents vs if a website wants to support HTTPs. You have to change a lot more in one go for email to be secure than you do for a given website.

josho 12y ago
Yup, it's going to be hard--lets just not bother. I get it, you've got to update SMTP, the mail client, and likely other points (mail storage). But that's no reason not to try. Look at DKIM and SPF--we've maid steps to protect against forgeries.
- 6d0debc071 12y ago
  I'm not advocating either way, I'm just saying that it's a problem with a higher barrier to clear since it requires far more buy-in to be meaningfully implemented. You can go and encrypt your email right now but unless you get an organisation with an incredible degree of power to back you you'll be sending messages most people can't read and recieving unencrypted stuff in return.