OSEC

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Re: Lab OS Choices

From: Peter Manis (manisdigital39.com)
Date: Mon Aug 13 2007 - 07:18:19 CDT


Shaon,

You were correct in what you thought I was looking for, I just really
don't know enough about pen testing yet to know what setups are most
effective for learning. With the equipment I have I probably can
setup a simulated inet.

Thanks for your help.

On 8/13/07, Shaon Diwakar <shaon.diwakaryahoo.com.au> wrote:
> Hi Peter,
>
> I was under the impression that you might have wanted to setup a pen test lab for attack & penetration type of work. As far as I know, there is no real learning benefit from working remotely versus locally - though, others on the list might have further insights? Then again, I'm sure using your existing hardware & creativity - you'd be able to simulate an external network locally :)
>
> Regards,
> sHz
>
> ----- Original Message ----
> From: Peter Manis <manisdigital39.com>
> To: "Shenk, Jerry A" <jshenkdecommunications.com>
> Cc: pen-testsecurityfocus.com
> Sent: Sunday, 12 August, 2007 1:40:32 PM
> 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 <jshenkdecommunications.com> 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: listbouncesecurityfocus.com [mailto:listbouncesecurityfocus.com]
> > On Behalf Of Peter Manis
> > Sent: Saturday, August 11, 2007 6:40 PM
> > To: pen-testsecurityfocus.com
> > 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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