Connecting Outlook 2007 to Exchange 2003 over VPN

Posted on 2010-09-21
Last Modified: 2012-06-27
I have an intermittent problem connecting Outlook 2007 to an Exchange 2003 server over my VPN.  I always use a hosts file on the computers and most of the time it works fine.  However, sometimes it does not.  The problem appears when I hit the "check name" button and it fails to resolve the user.  I have this problem about 25% of the time when I try to connect this way.  Outlook 2003 never has a problem synchronizing over the VPN to the Exchange server.

Any Ideas?
Question by:Kirchtoe
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Expert Comment

ID: 33729209
You must be using split tunneling and the DNS settings for DHCP are not resolving internal name/IP addresses. VPN should assign new DHCP settings w/ an internal DNS server.

If you can, stay away from hosts files.

Expert Comment

ID: 33730035
Are you using the fully qualified domain name?

^^ is right, stay away from host files, they are never a good idea.


Author Comment

ID: 33734218
I have a DNS and DHCP server on each side of the tunnel that handles those duties for each network.  On the LAN where I am trying to connect the Outlook client, where do I specify the FQDN?  Do I add it to my DNS or in DHCP.
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Accepted Solution

Richard1985 earned 250 total points
ID: 33734295

Depending on the IP ranges on each network I would specify the exchange server in the host file against local IP - if the network ranges are the same this would cause issues. This will effectively avoid DNS issues and should work.

Do not use multiple exchange entries such as:     Exchaange     Exchange.local

Instead use:
<local IP>       <Exchange name>.local

As duplicate entries can create loopbacks and crash Outlook over VPN - this was the cause of a similar issue I had. Try it and let me know.


Author Comment

ID: 33738808

I entered the complete FQDN of the server in my hosts file and it worked!

thank you

Expert Comment

ID: 33738825
You should still stay away from host files.

When you connect to the server, use the FQDN and it should connect without a host file entry.

Expert Comment

ID: 33742060
Glad that worked for you Kirch,

Personally I have never had issues using the FQDN only in host files as long as network IP ranges are different.

Thanks for the points :o)

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