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Routable VPN Between ASA and Windows RRAS

Unanswered Question
Feb 3rd, 2014
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Hi all,

I'm trying to figure out the best way to create a routable VPN between my production network and a small DR server that I have colo'd offsite.

On the production side I have an ASA 5515-X ( and on the DR side I have a Windows Server 2012 R2 server running RRAS, DHCP, NAT, and Hyper-V.  The DR server has a virtual environment with a subnet of behind NAT (diagram attached for a visual).  I've seen some tutorials online for how to create a routable VPN between the two, some utilizing the Windows Advanced Firwall to create an IPSec tunnel.  So far, I've not been able to get the tunnel to come up.

Before I spend even more time trying to troubleshoot this, I was wondering what the best way to create a secure connection between these two subnets is and if anybody has done something similar successfully.



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Jason Mon, 03/24/2014 - 10:55
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None yet, I've been stuck on this for a while now.  My latest attempt caused the DR site to go offline and required hands-on at the colo site to get it back online due to a bad ipsec policy, so I've backed off a bit on trying things.

grandisle Thu, 10/02/2014 - 07:11
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I am looking into the exact setup you are currently trying (or tried) to implement.  Did you have any luck?

Any words of wisdom and/or tips/tricks?


Jason Thu, 10/02/2014 - 07:49
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I've given up trying to make it work at this point.  I'm definitely interested in getting this to work still.  If I see any suggestions, I'm happy to guinea pig it :)




I had this problem myself right now. I didn't find any answer from Cisco's site, I'm going to post the one that I found on Microsoft site:


In the document says: "Cisco ASA being an End-Of-Line product, the OS update for these devices seem unlike". Well this information had helped me 2 weeks ago when I order the ASA firewall and choose another option.

I will try to implement the solution and tell you how it goes.


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