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Please post IPCONFIG /all <br />
<br />
when connected. &nbsp;
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what does that have to do with anything? &nbsp;they are getting connected successfully and are resolving using proper dns server to the proper mail host. &nbsp;The IP isn't the problem.
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What happens when he tries to open outlook?<br />
What do you mean by &quot;it works when connected to the modem directly&quot;<br />
How is the vpn client resolving names?<br />
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I think &quot;instaIT&quot; is on the right track, you should start by verifying the client is using the active directory dns server used by the exchange server and the internal fqdn of the exchange server resolves to the internal ip address of the exchange server.<br />
<br />
For example, <br />
ping exchange-server-name.domai<wbr />n.com <br />
from the client.<br />
<br />
Donnie 
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When I say it works when conencted to the modem directly, I mean that if the users home Dlink router is bypassed then the user can vpn in and open his outlook client and it will connect. &nbsp;Once we put the router back in the chain, it fails again.<br />
<br />
It definitely is resolving names using the right DNS server and then the address is in the host file as well as a backup. &nbsp;It can definitely hit the right interface via ICMP, but whatever reason when outlook tries to connect, it fails. &nbsp;What does outlook use to connect when you set it up for LAN use? &nbsp;Is it just tcp/ip? &nbsp;Any specific port that it uses?<br />
<br />
Thanks!
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The user can't get outlook connected to the exchange server configured with LAN settings when behind their home firewall and using our VPN. &nbsp;I would have set it up with RPC over https but unfortunatley they didn't go that route here. &nbsp;They can conenct when outside their router. &nbsp;The vpn tunnel is good because they can get to network drives, so I know that VPN passthrough is working fine. &nbsp;Any thoughts on how to troubleshoot this? &nbsp;The name is resolving correctly as well. &nbsp;Any help would be greatly appreciated.
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The user can't get outlook connected to the exchange server configured with LAN settings when behind their home firewall and using our VPN.  I would have set it up with RPC over https but unfortunatley they didn't go that route here.  They can conenct when outside their router.  The vpn tunnel is good because they can get to network drives, so I know that VPN passthrough is working fine.  Any thoughts on how to troubleshoot this?  The name is resolving correctly as well.  Any help would be greatly appreciated.

User is VPN'ed into the office and can't connect to the exchange server using the outlook LAN settings, it works when connected to the modem directly though.

Microsoft Outlook is a personal information manager from Microsoft, available as a part of the Microsoft Office suite. Although often used mainly as an email application, it also includes a calendar, task manager, contact manager, note-taker, journal, and web browser.

Outlook

Exchange is the server side of a collaborative application product that is part of the Microsoft Server infrastructure. Exchange's major features include email, calendaring, contacts and tasks, support for mobile and web-based access to information, and support for data storage.

Exchange

Hardware-based firewalls provide more sophisticated protection for inbound and outbound traffic than the simple Windows software firewall or the basic NAT firewalls found in routers. These devices implement techniques such as stateful packet inspection, deep packet inspection, and content filtering; and may include built-in antivirus and anti-malware protection.