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Configure Persistent VPN Connection

Posted on 2010-11-23
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Last Modified: 2012-05-10
I am evaluating a could based Server.  The OS is Windows Server 2008, I need that server to maintain a persistent VPN connection to my network since this Server will be a member of the Domain and will need to use Active Directory.

We have a Cisco ASA5505 on the edge of this network, I'd like the sever to connect via VPN when it boots and maintain the VPN connection.

How do I configure this?

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Question by:SYOUNG
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5 Comments
 
LVL 7

Expert Comment

by:marektech
ID: 34196703
You say you have a Cisco ASA 5505 on the edge of this network. What have you got on the other side? The best would be to create a site to site VPN between your ASA and the firewall at the server host.
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Author Comment

by:SYOUNG
ID: 34196829
The other Server is in the cloud so there is no device on the other side to configure a site-site vpn connection.
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LVL 71

Accepted Solution

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Qlemo earned 500 total points
ID: 34208006
Create an OpenVPN (free) network as a peer-2-peer connection and OpenVPN running as a service. That would allow for SSL-based always-on connection.
Use ShrewSoft VPN or Cisco Client in batch mode on W2008 to establish a client VPN connection.
Windows 2008 itself is only able to maintain VPN based on PPTP, L2TP/IPSec, or IPSec with IKEv2. Those are not available at the Cisco side, AFAIK.

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Author Comment

by:SYOUNG
ID: 34215044
Downloaded and configured Shrew.  Created a batch file, the batch file runs fine alone but when I try to create it to run as a service I can't get it to work.  I also created a sheduled task to run the .bat file at startup but that doesn't seem to work either.
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LVL 71

Expert Comment

by:Qlemo
ID: 34216364
Did you try without using a batch file? Just the bare commandline?
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