[ubuntu-uk] OT - secure email?

Jon Spriggs jon at sprig.gs
Tue Sep 3 12:51:22 UTC 2013

OK, there's a longer form version of it on a recent Security Now
podcast (again, Steve Gibson), but the long and short of it is that
the NSA (and GCHQ, and I'm sure there are many many more) are (in
theory) inspecting traffic upstream of the various Data Centres that
Google, Yahoo, et al are using, and therefore, unless your S2S (Server
to Server) connections are also using TLS (only Google supports that,
I believe) then no matter how "secure" your C2S (client to server)
connection is, no matter how much your ISP promises not to inspect the
content, whenever the resultant mail leaves that server and crosses an
interception point, it will be parsed by government agencies.

There are rumours (although, I don't recall the source) that NSA etc.
are requesting the expired TLS certificates from companies such as
Google, so they can decrypt the stored-for-later-decryption collection
of packets.

Ultimately, we should have moved off SMTP as a communication method
many years ago (in the same way we moved away from telnet and FTP),
but it's an easily understood and implemented protocol that
non-techies can grasp. The move from HTTP->HTTPS was prompted by the
financial industries worried about the risks of interception, but this
is easily controlled because the focal point of an HTTPS connection is
the same as the focal point of an HTTP connection, and so it's
relatively simple to redirect that HTTP (insecure) connection to an
HTTPS (secured) connection, just by saying "Don't ask here, ask over
there"... there's nothing inherent in the SMTP protocols (as far as I
can tell) that would do the same thing, plus the decentralized and S2S
nature of SMTP makes it much harder to say "Don't use plain text with
this host".

Just to clarify, I'm not saying MyKolab is particularly a bad actor
here (I don't really know much about them, beyond the fact that PJ
promoted them and Steve suggested that wasn't a great idea), but by
suggesting it is a "secure" host you are ignoring the underlying
problems in SMTP as a whole, especially as the initial question was
started with "Given the revelations about PRISM".

Personally, I'd prefer to see something on an always-on device such as
an Android or iOS phone that is physically local to you, which
provides your mail services - either using something like BitMessage,
or SMTP which has forced GPG encryption before relaying (ideally over
Tor), so that the communications are always managed by you... but this
won't happen until more people get concerned about this stuff.

Jon "The Nice Guy" Spriggs

On 3 September 2013 12:09, Alan Pope <alan at popey.com> wrote:
> On 3 September 2013 11:55, Jon Spriggs <jon at sprig.gs> wrote:
>> Sadly, even MyKolab isn't really secure [0]
> Got anything better than a single tweet from Steve "RAW SOCKETS!"
> Gibson? I have a hard time taking anything he says seriously.
> Cheers,
> Al.
> --
> ubuntu-uk at lists.ubuntu.com
> https://lists.ubuntu.com/mailman/listinfo/ubuntu-uk
> https://wiki.ubuntu.com/UKTeam/

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