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Sorry for the confusing question earlier. I have edited it to make it to be more in accordance with the site.

I am conducting a penetration test on a network where they have Windows 2008 R2 for all the servers (File server, DC etc) and Windows 7 for desktops(end users). One thing I have found that they are somewhat behind on patching schedule, but nothing serious so as to get a shell on any important system.

I understand it is difficult to get a shell straight away on these systems, thus I want to know what procedure people follow when testing such secure networks. What should be my methodology to tackle this situation and where should I focus most?

TIA

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What tools are you using ? How did you scan the network ? Do know that its not THAT easy to get shell on Win 2008 R2 and Windows 7 unless some real crappy piece of software is running on with known vulnerabilities. – asudhak Sep 24 '12 at 13:00
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I don't see how anyone can provide information in order to help you based on the information you provided. It sounds like they are either better off then you realize. I do hope you will patch their systems for them, why you would do pentration testing on known fixed exploits confuses me. Furthermore something is odd about this question and fires off my spider senses. – Ramhound Sep 24 '12 at 13:01

closed as not a real question by Terry Chia, Iszi, Jeff Ferland♦ Sep 24 '12 at 15:35

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