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Author Topic: Pen Testing VMWare Image  (Read 5042 times)
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hyro
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« on: September 23, 2010, 05:34:52 AM »

Hi there,

I think I have found the right forum section - I will be starting my final year at uni soon and we will be doing some pen testing using VMWare images. What I would like to know and what I haven't been able to find out is, is it easy?
We will be given a few images of a web server, a workstation (and something else) to work on

I have identified Nikto as the tool to use to pen test the web server image.

What I am trying to get at is how is Backtrack used to 'connect' to the virtual image?

I'm so confused - I think I may fail all of this  Sad
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hayabusa
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« Reply #1 on: September 23, 2010, 07:21:05 AM »

Assuming the point of the class is to train you for real-world scenarios, then it really should be simulation of physical boxes, etc, and the VM images should be treated no differently than physical servers / machines on the network, for the most part.  Assumably, they'll still be attached to a 'network' of some sort (physical or virtual,) so reconnaissance / info gathering, attack vectors, privilege escalation and covering tracks should all be done the same way.

The OSCP certification (and CEH for that matter) that are discussed a lot on this forum all use VM images to practice against, as it aides the course instructors in making sure multiple students have access to the same 'build', for learning purposes.  Many of us on here use VM's (VMWare, Hyper-V, Xen, etc) for testing in our labs.  The only real difference, depending upon the type of practice you want to get, is the lack of routers / firewalls in between, in some cases, etc.  But if they're teaching you how to go after the boxes, themselves, once you can 'see' them, then it's no different, for your purposes.

Connecting BackTrack is as simple as booting it, giving it an IP, and using it to go after the VM, just as you would a physical box on the network.

As for your webserver image, Nikto, Samurai WTF and MANY other tools and distros exist, for the purposes of Web server / web app scanning.  You'll have fun!
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~ hayabusa ~ 

"All men can see these tactics whereby I conquer, but what none can see is the strategy out of which victory is evolved." - Sun Tzu, 'The Art of War'


OSCE, OSCP , GPEN, C|EH
dante
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« Reply #2 on: September 23, 2010, 09:35:12 AM »

Hi there,

I think I have found the right forum section - I will be starting my final year at uni soon and we will be doing some pen testing using VMWare images. What I would like to know and what I haven't been able to find out is, is it easy?
We will be given a few images of a web server, a workstation (and something else) to work on

I have identified Nikto as the tool to use to pen test the web server image.

What I am trying to get at is how is Backtrack used to 'connect' to the virtual image?

I'm so confused - I think I may fail all of this  Sad
I will try to give you a picture of how typically it all works.

Your host os can be any OS of your choice.
One of your guest os will be backtrack and the other guest os will be the webserver image. If you have chosen "bridge" mode while configuring both the VMs then you will see both the machines as a part of your LAN connected directly to the router. Both the webserver VM and backtrack VM are now in the LAN. You can attack the webserver VM, from the backtrack VM.
But setting up your VMs in bridge mode should be AVOIDED unless they are patched.
You should instead use "host-only" mode while configuring the VMs as a vulnerable webserver image is involved.
If this does not make much sense now, once you are setting up the vms yourself you will get the full picture. Just get in and start getting your hands dirty. You will be fine.

Dont be scared. If you enjoy hacking this will be the most fun you ever had in your academic life.
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H1t M0nk3y
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« Reply #3 on: September 23, 2010, 12:32:24 PM »

Quote
I'm so confused - I think I may fail all of this

Don't get discouraged at the start! People one this forum have all started at this point and we have all made it through!  Wink

Try what dante and hayabusa proposed and post your feedback, we will then help you!
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OSCP, GPEN, GWAPT, GSEC, CEH, CISSP
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