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Accessing email through IPSec VPN

Posted on 2010-03-30
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Last Modified: 2012-05-09
I have a small network with a Watchguard firewall and using IPSec as my VPN access. The problem i have is with emails. I have an Exchange 2007, Server side, and Outlook 2007 client side.
When i connect to the network through my VPN, i cannot get updates to my outlook. I've tried everything i can think of and nothing seems to be working.
Does anyone have any idea what i'm doing wrong? Any help would be greatly appreciated...
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Question by:NFMC
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13 Comments
 
LVL 6

Expert Comment

by:Mailroot
ID: 29120867
Now this is Server side Article ; http://support.microsoft.com/kb/320027, but should be a concern

-Ethan
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LVL 20

Expert Comment

by:Rick Fee
ID: 29120883
If you ping the local name of your Exchange server do you get proper name resolution?
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Author Comment

by:NFMC
ID: 29122031
NO, I am unable to ping the name, however, i can ping the ip address.
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LVL 13

Expert Comment

by:murgroup
ID: 29126844
Easiest thing to do is create an entry in the host file on your workstation that points to the exchange server. Host file is in c:\windows\system32\drivers\etc.
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Author Comment

by:NFMC
ID: 29189710
I tried editing the Host file , but still does not work.
I can ping the ip address
I can ping the FULL domain name, but i can't ping the name and get a full translation.
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LVL 2

Expert Comment

by:markswelch
ID: 29253089
You can add your domain into the the DNS Suffix for the network adapter, any request not an FQDN will be resolved as host.yourentereddomain.com.
Network Adaptor, TCP/IP stack, advanced, DNS tab, "DNS suffix for this connection"

You could also use and hand out via WINS via your VPN IP DHCP Pool

Hope this helps
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LVL 20

Expert Comment

by:Rick Fee
ID: 29253604
Is your AD namespace the same as the public namespace?
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LVL 20

Expert Comment

by:Rick Fee
ID: 29253725
Sorry that is AD DNS namespace....is it the same as the internet DNS name space
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LVL 13

Expert Comment

by:murgroup
ID: 29372660
Want to confirm also your using two different subnets? This can cause issues if both main office and remote are on the same subnet.
ie.
Office: 192.168.1.0
Remote: 192.168.2.0
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Author Comment

by:NFMC
ID: 29449721
Yes, AD DNS namespace are the same and I'm on two different subnets.
However, I do not have a WINS server, do i need to set one up?
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LVL 20

Assisted Solution

by:Rick Fee
Rick Fee earned 2000 total points
ID: 29456272
Ok I have ran into this issue...I have run into this a few times in the past.    You have to change the bind order...the problem is your remote client queries a internet DNS server.    I have a script that I placed in the VPN client to launch after the client has a connection.   This changes the DNS order and puts the AD DNS servers at the top so it queries it first.    I have attached the script.
http://support.microsoft.com/kb/311218 

BindingOrderForVPN.vbs
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Author Comment

by:NFMC
ID: 30536791
EndureKona, sorry, but that did not work either...
Any other suggestions
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Accepted Solution

by:
NFMC earned 0 total points
ID: 32259357
I finally resolved this issue by updating the Watchguard Client VPN software. It turns out to be a bug fix in the latest upgrade and this was the first issue to report it. Everything is working well and I really appreciate everyone's help in this matter. THANKS!!!
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