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One of our web servers just failed PCI-DSS compliance because the vuln. scan detected the OS was Windows Server 2003 Service Pack 1 (obviously very outdated!).

My question is how did the vuln scan detect this as I can't seem to find a way to source the same information without having AD access to that box (it's on a service providers network). Even with nmap, it only provides guesses to the OS version:

Aggressive OS guesses: Microsoft Windows Server 2003 SP1 or SP2 (99%) So how do I verify this before sending a very, very angry email to our provider? If this is accurate, then I'd say this is negligence and my email tone to them won't be very good.

I have no login access to this box.

  • 1
    Have you tried fingerprinting using metasploit / armitage? – James May 8 '13 at 21:40
  • Can't you just ask the person who discovered this issue how they determined it? I assume they work for your company in some capacity. – Ramhound May 8 '13 at 22:34
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Close all ports. Reassign the port RDP. Modify the TTL. And most likely your system does not determine from the response).

Modify the TTL:

[HKEY_LOCAL_MACHINE\System\CurrentControlSet\Services\Tcpip\Parameters]
DefaultTTL 64 DWORD

Reassign the port RDP (mstsc :3333):

[HKEY_LOCAL_MACHINE\System\CurrentControlSet\Control\Terminal Server\WinStations\RDP-Tcp]
PortNumber 3333 DWORD

Reassign the VPN port:

[HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Control\Class\{4D36E972-E325-11CE-BFC1-08002bE10318}\0003]
TCPPortNumber <VPN port number> DWORD

Disable IPv6

HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Services\Tcpip6\Parameters
DisabledComponents 0xffffffff   DWORD

command, disable IPv6 Teredo, 6to4, ISATAP:

netsh interface teredo set state disabled
netsh interface ipv6 6to4 set state state=disabled undoonstop=disabled
netsh interface ipv6 isatap set state state=disabled

Change response services, and so on and so forth ...

Close all not need ports.

| improve this answer | |
  • while this is good information, unfortunately I think you missed in my OP where I stated we have no login access to this box. Also, simply hiding the leaked info is not a solution because the box is seriously vulnerable to even skiddies using metasploit and a definite PCI-DSS failure. – SnakeDoc May 8 '13 at 22:09
  • @SnakeDoc This station with W2K3 SP1 inside your perimeter or infrastructure? If so, you can influence the situation of software and hardware. If not, notify the administrative client and do not strain). – STTR May 8 '13 at 22:45

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