On Mon, Jun 29, 2015 at 1:48 PM, Michelle Sullivan <[email protected]>
wrote:

> Brandon Long wrote:
> >
> >
> > On Fri, Jun 26, 2015 at 7:03 PM, Michelle Sullivan <[email protected]
> > <mailto:[email protected]>> wrote:
> >
> >
> >
> >     Sure SMTP can have the lowest common denominator, but I thought the
> >     whole point of the protocol and extensions was:
> >
> >     1/ You want to ensure the email is not readable by a 3rd party you
> >     encrypt (PGP/SMIME) it..
> >     2/ You want to ensure credentials for SMTP-AUTH are not
> >     compromised you
> >     SSL3/TLS/TLSv1.2,DH=4096 the connection
> >
> >     and what you don't do is:
> >
> >     3/ Encrypt the connection so no-one can see my email in transit....
> >     because yeah sure all servers will always TLSv1.2....
> >
> >
>
> Yeah probably was a little to matter of fact there.. probably should
> have saved, edited and sent later.
>
> > The point I have about bringing up Snowden is that for bulk
> > collection, they'll go where they can and find the weak link.
>
> I understand that, which means the sending or receiving computers unless
> they can hitch in a snooping point somewhere in between....
>
> > We won't be that link, if I can help it.  We have a ways to go, of
> course.
>
> .... however that's not necessarily going to stop with all the counter
> measures because someone will allow it, but as you correctly pointed
> out, at least it won't be you.
>
> >
> > Especially since #1 for everyone is a really long pole.  Sure, if
> > you're an actual target, #1 is a minimum... or not using this
> > infrastructure at all might be an even better choice.
>
> The main concern I have is if I want to exchange email, you're going to
> make it mandatory that I TLS 1.2 all connections with you?  (or you with
> me..?)
>
> Here's my thought (and where it gets complicated)
>
> If I request to send unencrypted, I expect you to accept it.
> If I request to send encrypted I expect you to at least keep the
> encryption to the level I have requested (and possibly try to negotiate
> higher levels if both servers can agree.)
>
> If you send to me and request encryption an I don't support (or to the
> level you request) it you can make a policy decision whether to continue
> (as I can in reverse.)
>
> Now the complicated bit....
>
> Who says what should or should not be encrypted?  Well when it comes to
> what should be encrypted that's easy... The person sending, if they want
> encryption then their desire for encryption should be honored or them
> given the option to go elsewhere.  If the person sending is not bothered
> about encryption encrypting or not is totally optional at the providers
> preference.
>
> Now the problem here is for the end user to request a encrypted email
> the *only* way to ensure that is by encrypting the email itself because
> as a provider of a service by it's very design was not intended to be
> encrypted (and lets face it transport layer encryption is an optional
> bolt on) is to deliver it yourself to the server that the destination
> email address (and storage) resides on, and as you know with your
> service that's just not possible (practically or with any sort of
> scalability.)
>
> Now when it comes to that policy as a provider you can say, "Ok all
> email transport will be encrypted to 'this' standard leaving our network
> or will not be sent" as a policy and "All email transport inbound must
> be encrypted to this standard or it will not be accepted" problem is do
> the users want that for the very small percentage of email that should
> be encrypted...?
>
> Note: My servers require authentication for relay, all authentication
> sessions must be encrypted (for the actual authentication and the
> remainder of the authenticated session.)  My MX servers (in and
> outbound) do not required transport layer encryption... and currently
> won't even support it (and I don't actually want to support it - too
> many SSL library root hacks in the past for me to trust high volume
> gateways to end user attacks... same reason I force only the login and
> registration and personal details on the website into the TLS sessions
> and force it back to plain text for 'normal browsing' (it's easier to
> spot hacks/attempts where there is little traffic rather than in streams
> of data to the order of gigabytes per day) - obviously that works for
> me, and wouldn't work for the likes of Google+ and Facebook because it's
> mostly personal details, but I'm sure you get the point.)
>
> Thoughts/comments welcome.
>

Sure, there's a bit of political or privacy argument involved here, that
some people think "why does this need to be encrypted".  There does seem to
be a shift, however, to encrypting by default.  The Mozilla blog post has a
bunch of pointers in it for reasons and calls to encrypt by default:

https://blog.mozilla.org/security/2015/04/30/deprecating-non-secure-http/

I don't expect to convince folks of that in this forum, nor to downplay the
costs of doing this, and the challenges for interoperability.

That said, so far today, only 0.015% of our outbound messages that were
over an encrypted link were using SSLv3.   At our volume, that's not
nothing, unfortunately, but it's a pretty small amount to allow to continue
to allow the possibility of breaking the rest.  TLSv1 is still about 5%,
way too high to deprecate at this point.

Inbound is 0.1% at SSLv3, 37% at TLSv1.

Also apropos https://tools.ietf.org/rfc/rfc7568.txt

I know, this is somewhat off-topic for the DHE length, but there you go.

Brandon
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