RE: Lab OS Choices



I've found a few tests that worked against virtual machines but did not
work against real machines. I agree, in most cases, there really is no
difference.

I also have some routers in my lab. That way, I can set up egress
filtering between the servers and the attackers in the lab. That will
help you get some realism about some things, particularly local exploits
of machines inside the network (like an Exchange client attack). I
think that also increases your credibility when talking with
clients...for example, "In the lab, we set up egress filtering...blah,
blah, blah...and with the filtering enabled, the remote exploit of the
Exchange client worked in that it crashed the client but it made it much
more difficult to get to a command-prompt on that box." That's not
really part of the pen-test itself but the real goal of the pen-test is
to make the network more secure and it definitely goes toward explaining
to the client how to make their network more secure.

-----Original Message-----
From: listbounce@xxxxxxxxxxxxxxxxx [mailto:listbounce@xxxxxxxxxxxxxxxxx]
On Behalf Of Peter Manis
Sent: Saturday, August 11, 2007 11:41 PM
To: Shenk, Jerry A
Cc: pen-test@xxxxxxxxxxxxxxxxx
Subject: Re: Lab OS Choices

Is there a benefit to performing pen tests on physical machines vs
virtual machines? I was under the impression that for the most part
the differences are very slim.

Shaon you mentioned that you thought I wanted to test remotely. It
isn't that I don't want to I just figured for a lab it would be fine
to do it internal. Is there a learning benefit to working remotely vs
locally? I don't mean local like attack ip = 10.0.10.1 and victim ip =
10.0.10.2 both with a 24 bit subnet I mean with routers in between and
subnet changes, etc.

Thanks.

PM

On 8/11/07, Shenk, Jerry A <jshenk@xxxxxxxxxxxxxxxxxxxx> wrote:
You definitely want something that you can exploit so that you can
lean
how the exploits work. You also want to have a variety of operating
systems with a variety of patch levels. I'd also recommend having
enough stuff so that you can test a lot of the operating system that
you'll run into. Having said that, you also need to start
somewhere...then you lab can grow.

I think I'd start with an unpatched Windows 2000 server. There are a
ton of exploits and you can get a good handle on how stuff works.
Honestly, you aren't gonna run into too many unpatched W2K boxes out
there so once you have that box set up, image the drive and start
applying service packs. You will run into W2K boxes with a couple
service packs but not all of them. You'll also want to have a box set
up that is fully patched so that you can understand how your exploits
work against a patched OS.

Another really nice, fun system is a Windows 2003 server without any
patches. You'll also want to take that unpatched W2003 server and
take
an image of that up to the end of March. That's fairly current but
still vulnerable to some REALLY nasty exploits - RPC/DNS for one lets
you own the box and in most cases, the box you'd be owning would be
the
DNS server which also has AD so you can create a user and make them an
enterprise admin...definitely a HUGE hole for a relatively recent OS.
BTW, you can also play with that same exploit on any other DNS server
that's a DC....really nasty!

You want to play with some workstation-class exploits too. Set up a
mail server and an exchange client so you can do some of the exchange
client exploits.

When I'm talking about "setting up a box", I have a couple old servers
with drives that I swap around for this type of stuff....stuff people
were throwing out. So for me, "a box" is really just a single drive.
If you get used equipment, wipe the drives before you mess with 'em.
You really don't want to accidently leak somebody else' data. I know
this is a lab environment and it shouldn't "leak" but still...they
probably didn't wipe the drive or I certainly wouldn't trust 'em.

VMware is also very popular. Each individual machine also fits my
definition of "a box". I would recommend that you have at least a
couple "real machines" that you use but VMware is a really slick way
to
test things out. There are some attacks that act differently on
VMware
and a "real machine"....that's why you have a lab, so you can learn
those differences.

-----Original Message-----
From: listbounce@xxxxxxxxxxxxxxxxx
[mailto:listbounce@xxxxxxxxxxxxxxxxx]
On Behalf Of Peter Manis
Sent: Saturday, August 11, 2007 6:40 PM
To: pen-test@xxxxxxxxxxxxxxxxx
Subject: Lab OS Choices

I am new to the world of pen testing and am working on building a lab.
What operating systems and versions do you recommend for a good all
around lab. Windows of course is a big one, but do you go back to 98?
Being a beginner I would think having all the patches on XP or Vista
might make it difficult to learn. I would also think adding a secure
OS like openbsd would be a waste of time for a beginner to try to gain
access to. All advice is appreciated.


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