Subject: [perpass] Mail encryption as an example

From: Yaron Sheffer <[email-masked]>
Date: Sat, 17 Aug 2013 14:51:24 +0300

Hi,

Stephen mentioned that S/MIME is not good enough because headers 
(to/from) are still exposed. But there's still tons of benefit when the 
content is encrypted, even if the metadata is exposed (provided users 
know that it is exposed, of course). E.g. I would like all my internal 
company email to be encrypted, even if tracing recipients is trivial for 
the attacker.

In other words, is the scope of the mailing list/solutions limited to 
security of individuals, as opposed to organizations?

 From a deployment perspective, I think we know how to provide privacy 
("identity protection") only by using heavyweight solutions, such as 
onion routing. But there's a whole lot of important things we could do 
(make S/MIME usable, standardize OTR, revive IPsec OE) if we remove this 
constraint. Are such items in scope of this discussion?

Thanks,
     Yaron

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From: Stephen Farrell <[email-masked]>
Date: Sat, 17 Aug 2013 12:59:05 +0100

On 08/17/2013 12:51 PM, Yaron Sheffer wrote:
> (to/from) are still exposed. 

Didn't really mean "not good enough", more that protecting those
headers would be my favourite improvement to make.

> But there's still tons of benefit when the

Absolutely.

I think there is a qualitative difference between this discussion and
our usual security protocol discussions - in the latter case (as you
say above) we always aim for "strong" mechanisms, where even the
weakest link is "strong."

In this case, its not quite so clear - it could well be that less
strong mechanisms would produce a better outcome - opportunistic
encryption for example as you also mentioned above - if they for
example increase the cost of pervasive passive monitoring sufficiently
or change the set of endpoints at which such monitoring is doable
so that those endpoints might not be seen as good partners with
whom to co-operate, for folks who would like to monitor.

S.

> 
> Thanks,
>     Yaron
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> [email-masked]
> https://www.ietf.org/mailman/listinfo/perpass
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>

---

From: Russ Housley <[email-masked]>
Date: Sat, 17 Aug 2013 14:25:46 -0400

There is a technique for protecting the subject line for S/MIME, but the recipients MUST be exposed for the mail to b delivered.  This exposure can be limited to the clients and various mail servers if SMTP/POP/IMAP are run over TLS.

Russ

On Aug 17, 2013, at 7:51 AM, Yaron Sheffer wrote:

> Hi,
> 
> Stephen mentioned that S/MIME is not good enough because headers (to/from) are still exposed. But there's still tons of benefit when the content is encrypted, even if the metadata is exposed (provided users know that it is exposed, of course). E.g. I would like all my internal company email to be encrypted, even if tracing recipients is trivial for the attacker.
> 
> In other words, is the scope of the mailing list/solutions limited to security of individuals, as opposed to organizations?
> 
> From a deployment perspective, I think we know how to provide privacy ("identity protection") only by using heavyweight solutions, such as onion routing. But there's a whole lot of important things we could do (make S/MIME usable, standardize OTR, revive IPsec OE) if we remove this constraint. Are such items in scope of this discussion?
> 
> Thanks,
>    Yaron