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Network Security Pen-Test
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RE: Pentesting using Vista?

Subject: RE: Pentesting using Vista?
Date: Sun, 23 Mar 2008 14:46:30 -0700
Vmware is a poor choice for hosting a pen/recon toolset.  I suspect that to be 
true of anything like QEMU or Virtual PC, too.  

Tools like nmap and hping give misleading results and horrible response, when 
piped through a virtual adaptor. In the case of Vmware, there are between 10 
and 15 messages passed from the vm to the host and back - just to transmit a 
single packet/datagram.  

The vnetworking stack also works like a transparent layer 2 proxy - altering, 
normalising and 'optimising' network behavior for the expected workloads  I 
have wasted hours of mapping time this way in the past, and would save you the 
trouble of trying it...

Also, Vista as a host needs to have the firewall and IPsec filtering disabled. 

The OS is also subject to the connetion and pacet rate filtering that was 
introduced for XP SP2.  There are unauthorized binary patches that must be made 
to TCPIP.SYS, for either OS to function as a testers platform.  Otherwise scans 
crawl to zero, and usefull open SYN traffic waits for timeouts in a limiting 
queue, before new SYNs are sent. Add the message-passing latency of your VM 
stack, and this is intolerable.

This is one case where the addage "right tool for the right job" applies.  
Vmware and Vista may have merits for certain applications.  In the pentest 
environment, these should remain as targets - where they will not impede the 
investigator, nor obscure  meaningful network information from examination.

Jeremiah

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