From: M Bealby (mbealby@gmail.com)
Date: Sat Jul 22 2006 - 02:59:17 EDT
From: wymerzp@sbu.edu
Subject: VMware and pen-testing
Date: 21 Jul 2006 17:59:06 -0000
> Hello, I am a student of computer science trying to learn more about
> the art of pen-testing. I have several tools at my disposal: nmap,
> enum, Metsploit Framework, Cain and Abel, ect. I obviously cannot
> test these against commercial networks (I could but I certainly
> don't want to go to jail) I have used nmap though due to it's
> unobtrusive nature. I therefore downloaded the evaluation version of
> VMware. I set up virtual machines with a host only connection;
> furthermore, I see the virtual machines network connections in
> network connections. I am running windows XP. I cannot figure out,
> probably due to my inexperience at networking, how to connect to the
> machnies once I have them up and running so I can run nmap scans
> against them (among other things). Any help would be appreciated,
> including links or whatever knowledge you guys could pass on.
> Regards, Zach
Hi Zach,
Virtualisation is an excellent method of creating lab environments for
practicing penetration testing. You mentioned you downloaded the
evaluation version of VMware. Now this might be what you are
referring to, but VMware Server 1.0 [1] was released for free recently and
is great for this kind of testing.
Linking all your virtual machines with host only networking sounds
like a good start, especially if you are new to the art. It will
avoid any mistakes affecting your local network / Internet connection.
To link the machines together you create a virtual network (which will
be called VMnet X, where X is a number from 1 to 9). If you place
this network in host-only mode it acts like a virtual switch, routing
packets between virtual machines with network cards allocated to that
VMnet. Some VMnet's are reserved, and I'm not exactly sure how it is
done on Windows, but each VMnet will be allocated a (user-specified)
IP range.
For example, let's assume you setup VMnet 5 to be host-only networking
on the network 192.168.140.0/24. Then, to link your virtual machines
together across this switch you will need to add a network card to
each virtual machine and point it to VMnet 5. In addition to this you
will need to setup the networking information in each guest operating
system to have an IP in that range (e.g. for two virtual machines,
192.168.140.10 and 192.168.140.11). If all is done correctly, they
should be able to ping and communicate between each other.
One thing to note is that if you are running host-only networking and
are attempted to connect to the machines from the host operating
system (the one running VMware) you will not be able to see them (I
think). Because of this I suggest creating a new virtual machine
running one of the live-cd based penetration testing Linux
distributions such as back:track [2]. This is probably the easiest
method to get plenty of tools to practice with in your lab.
Now that you have the attacking side set up you should install a
variety of operating systems to attack. I would recommend installing
a few older Linux/BSD distributions (without updates), as these will
have known flaws that can be exploited easily. Also install a couple
of newer distributions to observe the differences. The main
difference should be that the newer distributions are normally more
secure 'out-of-the-box'. A great advantage about using Linux/BSD for
this purpose is that it is all free of cost. Another free operating
system you might want to try is Solaris [3].
However, if you wish to install some Windows based machines (and to be
complete, you should) then Microsoft makes trial editions (90 days) of
most of their software available for free. The downloads are
scattered throughout the Microsoft website, but a Google search [4]
usually brings up a few.
I hope this helps you get started and good luck with your learning,
Martin
[1] http://www.vmware.com/server/
[2] http://www.remote-exploit.org/
[3] http://www.sun.com/software/solaris/get.jsp
[4] http://www.google.com/search?q=site:microsoft.com+trial
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