Accessing Server 2008 R2 from a remote access VPN pool using Cisco Client but S2008R2 is “Destination host unreachable”

Unanswered Question
May 10th, 2012

I'm using Cisco ASA 5505 IPsec VPN to access Locally, I can access to my 2003 server and reach shared folders, but in the same network 192.168.20.X, but I can't access to my 2008R2 server. I tried with different ways and nothing works.  

1> Connect from outside using Cisco Client. X.X.X.X to my local cisco IP-Pool (10.254.254.X)

2> In my Cisco configuration I allowed the access from my IP-Pool to my local network (192.168.20.X)

3> After connecting from outside, I can access to ALL my Map Drives and Shared files on local network 192.168.20.X (PC and 2003 server).

4> But my server (main one) File Server 2008R2 is “Destination host unreachable” and is in the same network 192.168.20.X.


PC's: ( to

Printer's: ( to

Servers: ( to 230)

I can access to everything but not to my Windows Server 2008 R2. And there are ALL my Company Files.

HELP Please.

I have this problem too.
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Alex LP Thu, 05/10/2012 - 17:36

Possible firewall on server

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Posted May 10, 2012 at 11:59 AM
Replies:1 Avg. Rating:
Views:941 Votes:0
Tags: windows, asa, 5505, 2008r2

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