IPSEC VPN tunnel between Cisco ASA 5510 and Windows Server 2008

Posted on 2010-01-08
Last Modified: 2012-05-08
I've set up several tunnels like this between the ASA and Server 2003, but this is the first time I've needed to set one up on Server 2008.  The configuration interface looks the same as it did on 2003 and I've configured all the settings the same way I did before, but it isn't working.  I've been able to get ISAKMP portion of the tunnel to establish, but encrypted traffic never starts flowing over Protocol 50.  Does anyone have any experience with a similar setup?  Are there some behind the scenes settings that have changed from server 2003 to server 2008?

Question by:ChristianT
    LVL 33

    Expert Comment

    As a test, shut down the Windows 2008 firewall service.  And retry....maybe the firewall is block this setup..
    LVL 3

    Accepted Solution

    The firewall service is actually already shutdown.  It has been the whole time.

    Thanks for the suggestion.


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