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Re: What is being a pen tester really like?
From: "Diarmaid McManus" <diarmaidmcmanus () gmail com>
Date: Wed, 9 Aug 2006 21:38:12 +0100

Omar,

Unfortunatly, your comments about contracts is true. I was speaking
from an ideal situation, which, unfortunatly, as we all know, rarely
if ever happens.


I don't believe that saying that "no penetration should fail" provided only
that "all areas are covered" (i.e. without caring about any other kind of
restrictions) can be proved to be true in all cases.

Driving a car through the window of the buisness' offices and grabbing
the server counts as sucsessfull penetration in any case.. in an ideal
situation in which you are allowed drive a car/articulated lorry(more
fun, i'd assume) through your client window. ;)

a) We are always able to get in, then what is the benefit then for companies
to pay big bucks to perform these tests if everyone already knows the
results?

But do they know where these vulnerabilities lie? If we patch as many
vulnerabilities as we find, we seriously lower the risk of a
penetration ever happening by malicous attackers. They have timelimits
too in many cases ;) To quote Sun Tzu:

"Against those skilled in the attack, an enemy does not know where to
defend. Against the experts in defence, the enemy does not know where
to attack."

Strengthen security to the highest degree, and the attacker will
(hopefully) not know where the weakest point in your defenses are to
attack.

b) We can't always get in or provide proof that we can get in, then we have
called ourselves incompetent in front of the client, even if the assessment
was found useful for the client as an indication that they were doing
something in the right direction to increase security.

Not incompetent, if we talk to knowledgeable people, i.e your clients
IT staff, and let them know what a good job they've done at their
security policies, and say you couldnt find a way around them, i dont
think you'd be found incometent ;) (Unless of course a break in was
discovered a few days later, or, worse again, whilst you were
delivering your report to the managers et al ;) )


I strongly believe that being able to get in does not always reflect the
competence of the assessor (big mistakes by the client can make things
extremely easy, even for the most inexperienced and unskilled of the
pentesters). Likewise, not being able to get in shouldn't be a single good
reason to consider a pentester as incompetent :-).

I agree 100% here, if someone has one outward facing router with an
excellent firewall with all systems patched 100% and no known
vulnerabilities for them, etc etc, and no access is gained, the pen
tester cannot be called unskilled. If someone has an old BSD machine,
for instance, acting as firewall, with OpenSSH 1.x (*shudder*) for
administration, and the pen tester gets access, this hardly means that
(s)he's a good pen tester.

~Diarmaid

On 09/08/06, Omar A. Herrera <omar.herrera () oissg org> wrote:
Hi Diarmaid,

> -----Original Message-----
> From: Diarmaid McManus [mailto:diarmaidmcmanus () gmail com]
>
> Apologies, I was under the impression from my quick read that Kluge
> meant "Its a pen test if you don't _attempt_ a penetration" rather
> than "Its a pen test if you _fail_ to penetrate".
>
> However, no penetration test should fail. You should always be able to
> get access if your client allows you to cover all areas, such as
> Physical testing, Social Engineering, etc.

I agree that any pentester, given enough resources, skills, attack vectors
and time should be able to get in (same as with any attacker). The problem
is that I doubt that there are many contracts with such a scope (all which
I've seen at least include a restriction in time).

I don't believe that saying that "no penetration should fail" provided only
that "all areas are covered" (i.e. without caring about any other kind of
restrictions) can be proved to be true in all cases. Besides, that would
seem to imply that pentesters are experts in all areas (or that pentest
companies have experts in all areas).

Now, if we accept as a fact that pentest requires penetration or at least
proof that you can penetrate (in any case), we also are getting ourselves
into trouble. If:

a) We are always able to get in, then what is the benefit then for companies
to pay big bucks to perform these tests if everyone already knows the
results? Only to satisfy themselves that this is true? Wouldn't they be
better spending this money in reducing the risk rather than proving again
what we are considering an axiom?

b) We can't always get in or provide proof that we can get in, then we have
called ourselves incompetent in front of the client, even if the assessment
was found useful for the client as an indication that they were doing
something in the right direction to increase security.

I strongly believe that being able to get in does not always reflect the
competence of the assessor (big mistakes by the client can make things
extremely easy, even for the most inexperienced and unskilled of the
pentesters). Likewise, not being able to get in shouldn't be a single good
reason to consider a pentester as incompetent :-). There are many other ways
(imperfect but still more accurate) to assess how competent an assessor was
during a pentest (i.e. through measurable QA requirements).

Cheers,

Omar Herrera


> On 08/08/06, Dotzero <dotzero () gmail com> wrote:
> > On 8/8/06, Diarmaid McManus <diarmaidmcmanus () gmail com> wrote:
> > > Actually kluge, i think you'll find that that would be 'Its not
> > > nuclear weapons testing if there are no nuclear weapons', which, you
> > > will find, is actually not nuclear weapons testing.
> > >
> > > Penetration testing, by defenition, (and to keep many happy ill throw
> > > in IMO here) requires penetration of the systems you are testing, or
> > > at least proof that you _can_ penetrate them if you so wish.
> > >
> > > Yours,
> > > ~Diarmaid.
> > >
> >
> > I have to agree with Kluge. Penetration testing is testing the ability
> > to penetrate. That is different than saying that penetration is a
> > prerequisite for testing.
> >
> > You might have a very short report if you find no way of actually
> > penetrating but you still performed the test.
> >
> > Dotzero
> >



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