On Sep 9, 2013, at 9:26 PM, John R Levine <[email protected]> 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!

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.)

> 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.

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.

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