Re: not really pgp signing in van

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On Mon, Sep 9, 2013 at 9:41 PM, Ted Lemon <Ted.Lemon@xxxxxxxxxxx> wrote:
On Sep 9, 2013, at 9:26 PM, John R Levine <johnl@xxxxxxxxx> wrote:
> Um, didn't this start out as a discussion about how we should try to get
> people using crypto, rather than demanding perfection that will never
> happen?

Yes.

> Typical S/MIME keys are issued by CAs that verify them by
> sending you mail with a link.  While it is easy to imagine ways that
> could be subverted, in practice I've never seen it.

The most obvious way that it can be subverted is that the CA issues you a key pair and gives a copy of the private key to one or more others who would like either to be able to pretend to be you, or to intercept communication that you have encrypted.   I would argue that this is substantially less trustworthy than a PGP key!

The CA NEVER ever gives the user the key in any of the systems I have worked on.

VeriSign did offer a key recovery system for enterprise use with central key generation but the keypair is generated on the enterprise side and never passed to the CA.


Of course you can _do_ S/MIME with a non-shared key, but not for free, and not without privacy implications.   (I'm just assuming that an individual can get an S/MIME Cert on a self-generated public key—I haven't actually found a CA who offers that service.)

Comodo offers that exact service today.

https://secure.comodo.com/products/!SecureEmailCertificate_Signup


Now this product still has the usual problems of S/MIME and PGP in that there is no infrastructure that allows a receiver to easily acquire the certificate (except by bulk query on the CA LDAP server) and there is no way to know what the sending policy should be.

The key pair is generated in the browser using the _javascript_ mechanism (as far as I know, I have not checked but my understanding is that this is how it works).

Just applied for a cert for Safari on phill@xxxxxxxxxxxxxxx. Worked fine. 


But the process of getting the certificate into my email client is far from simple. Apple mail certainly has the capability to do S/MIME but the controls to enable it are buried deep.

 
> Same issue.  I can send signed mail to a buttload more people with
> S/MIME than I can with PGP, because I have their keys in my MUA.
> Hypothetically, one of them might be bogus.  Realistically, they aren't.

Very nearly that same degree of assurance can be obtained with PGP; the difference is that we don't have a ready system for making it happen.

I don't see the value of this argument.

We have to fix key distribution. We have to make the CA actions transparent. That means a redesign of that whole part of the technology. If we are looking forward to new email systems then we can combine PGP Web of Trust with S/MIME message formats.
 
E.g., if my MUA grabs a copy of your key from a URL where you've published it, and validates email from you for a while, it could develop a degree of confidence in your key without requiring an external CA, and without that CA having a copy of your private key.   Or it could just do ssh-style leap-of-faith authentication of the key the first time it sees it; a fake key would be quickly detected unless your attacker controls your home MTA or the attacked identity's home MTA.

Eliminate the CA and you eliminate the parties with the incentive to sell the solution.

Whatever scheme is picked to complete secure email there is going to be a problem finding end users certs and end user policies. And there may be a market for solving that problem just like there is a market for blocking spam. 

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