Penetration Testing: RE: Pen-testing remote VPN services over IP

["Pete Herzog" <pete () isecom org>]

Chris,

In the OSSTMM 2.5 we have included the following as well:

        -Enumerate the VPN servers using TCP/UDP scans.
        -Use scans searching for response to different IP Types Packets.
        -Use ike scans to fingerprint the VPN server implementation and version.

-Protocol Responses
        PPTP :  IP Type: 47 (GRE)       TCP: 1723
        IPSec:1.        UDP: 500 (IKE)
        IP Type: 50 (ESP)
        IP Type: 51 (AH)
        L2TP:1. UDP : 1701
        L2F:1.  UDP: 1701

        -Outline the VPN security policy using different authentication /
encryption algorithms.
        -Verify the existence of mechanism to control the client machine
misconfiguration and unfiltered ports
        -Check the ability of the client software to allow split tunneling (default
route to internet and static routes to the corporate network)

Sincerely,
-pete

Pete Herzog, Managing Director
Institute for Security and Open Methodologies
__________________________________________
ISECOM is the accreditation authority for the
OPST - OSSTMM Professional Security Tester and
OPSA - OSSTMM Professional Security Analyst


> -----Original Message-----
> From: Chris McNab [mailto:chris.mcnab () trustmatta com]
> Sent: Thursday, November 06, 2003 20:22 PM
> To: pen-test () securityfocus com
> Subject: Pen-testing remote VPN services over IP
>
>
> Hi,
>
> As part of some research I am undertaking recently, I'd like to
> know if any
> of you have any decent information relating to the following areas of
> _remote_ assessment of VPN services over IP.
>
> The topics I have covered and documented fully so far include:
>
> - IPsec enumeration, scanning for UDP/500 and using Roy Hills' tools
> (ike-scan) to identify the gateway
> - Various overflows relating to ISAKMP / IKE packets being sent
> to UDP/500,
> as in MITRE CVE
> - Offline aggressive mode IKE pre-shared key cracking, by sniffing VPN
> traffic and using IKECrack
> - Check Point aggressive mode IKE username enumeration (using Roy Hills'
> fw1-ike-userguess over UDP/500)
> - Check Point Telnet authentication service (TCP/259) user enumeration
> - Check Point information leak attacks that reveal network interface
> addresses, over both TCP/256 and TCP/264
> - Check Point RDP encapsulation filter bypass techniques, using UDP/259
> - Offline Microsoft PPTP (TCP/1723) MS-CHAP challenge-response cracking
>
> Two areas in which I've identified a need for tools are:
>
> - Check Point brute force password grinding tool for FWZ or IKE, to
> compromise SecuRemote username/password combinations
> - PPTP brute force tool, to compromise those user/password
> combinations also
>
> Does anyone know of such offensive brute force tools, or techniques I have
> missed (against ISAKMP and Check Point)? if so, any input would be greatly
> appreciated.
>
> Regards,
>
> Chris
>
>
> Chris McNab
> Technical Director
>
> Matta
> 18 Noel Street
> London W1F 8GN
>
> http://www.trustmatta.com
>
>
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