On Fri, Oct 17, 2014 at 02:59:26PM -0400, Ian Grant wrote:
> On Fri, Oct 17, 2014 at 2:49 PM, Bret Lambert <bret.lamb...@gmail.com> wrote:
> > Well, if, as Herr Schroeder seems to be implying, this is used to
> > avoid port scans, I'd look for traffic to/from address:port which
> > don't show up on scans.
> 
> That's why I want to hide it behind an ordinary service.

The point being, Herr Schroeder appears to be a man who would become
one of your users, and has apparently missed that step. A manual that
includes an advisory to do so would likely be a good idea.

> 
> >> Also, the VPN could be tunneled
> >> over HTTP if necessary.
> 
> > I know of at least one company which sells a product which doesn't
> > just read headers, but classifies traffic based upon behavior, e.g.,
> > "small request receives large response -> bulk transfer", or
> > "series of tiny packets which receive a single, larger response ->
> > interactive session". I assume nation-states have developed similar
> > capabilities.
> 
> That's fine. But they have to analyze all the traffic. This is a
> needle in a haystack.

It's a good thing we don't know any nation-states that analyze all
the traffic, then. That would probably be bad.

> 
> > The ability to use statistical methods to eavesdrop on encrypted
> > SIP sessions comes to mind as an example of traffic analysis as a
> > tool to defeat adversaries who are attempting to secure their
> > communications.
> 
> Again, a needle in a haystack.

Assuming that your adversary is going into this blind, and hasn't been
given a list of interesting targets that includes your systems. States
also have access to human intelligence as well.

> 
> Please read the OP before refuting stuff on the list. If you want to
> argue, and you aren't sure of your argument, e-mail me off the list.
> Otherwise it just adds to the general level of confusion, which is
> already higher than I'd expected on this list.

Quoting the original email you sent:

> If anyone here has a better idea, or any other useful advice (even if
> it's "this has already been done!" or "It won't work," but please
> explain exactly why.) or pointers

I'm not attempting to refute the validity of what you're attempting,
I'm pointing out things that probably should be taken into consideration
during implementation/deployment, which I think falls under the heading
of "useful advice". Whether or not it's useful is a judgement left to the
reader.

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