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As a test, shut down the Windows 2008 firewall service. &nbsp;And retry....maybe the firewall is block this setup..
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As a test, shut down the Windows 2008 firewall service.  And retry....maybe the firewall is block this setup..

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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. &nbsp;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. &nbsp;I've been able to get ISAKMP portion of the tunnel to establish, but encrypted traffic never starts flowing over Protocol 50. &nbsp;Does anyone have any experience with a similar setup? &nbsp;Are there some behind the scenes settings that have changed from server 2003 to server 2008?<br />
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Thanks,<br />
Christian
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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?

Thanks,
Christian

IPSEC VPN tunnel between Cisco ASA 5510 and Windows Server 2008

Cisco PIX is a dedicated hardware firewall appliance; the Cisco Adaptive Security Appliance (ASA) is a firewall and anti-malware security appliance that provides unified threat management and protection the PIX does not. Other Cisco devices and systems include routers, switches, storage networking, wireless and the software and hardware for PIX Firewall Manager (PFM), PIX Device Manager (PDM) and Adaptive Security Device Manager (ASDM).

Cisco

Windows Server 2008 and Windows Server 2008 R2, based on the Microsoft Vista codebase, is the last 32-bit server operating system released by Microsoft. It has a number of versions, including including Foundation, Standard, Enterprise, Datacenter, Web, HPC Server, Itanium and Storage; new features included server core installation and Hyper-V.

Windows Server 2008

A virtual private network (VPN) is a network that uses a public telecommunication infrastructure, such as the Internet, to provide remote offices or travelling users access to a central organizational network securely. VPNs encapsulate data transfers using secure cryptographic methods and other security mechanisms to ensure that only authorized users can access the network and that the data cannot be intercepted.