Why is user unable to access Outlook when connected to the VPN?

Tags:
Exchange 2003
Microsoft Outlook
VPN
We are using Exchange Server 2003. One user cannot authenticate to Microsoft Outlook using her domain account and credentials when connected through the virtual private network (VPN). Even though she is using her domain credentials, she receives a message stating that she is using a wrong password and cannot authenticate. When she is directly connected to the local area network (LAN) using the same credentials, she has no problem accessing Outlook. I can establish connection between the Exchange server and her computer when she is connected through the VPN. The problem is only the Outlook authentication.

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What type of VPN is this person using? Is it the Microsoft VPN established with the Routing and Remote Access Service, or is it a third-party VPN such as one from Cisco or SonicWall.

If it is the latter, then there is a good possibility that the firewall, or whatever device is managing the VPN, is not passing NetBIOS traffic or that the end-user does not have the DNS and/or WINS server of the LAN configured for the VPN connection.

One possible and straight-forward solution to this is to create entries in the HOSTS and LMHOSTS file that correspond to the LAN IP address of the Exchange Server. Entries in those files will help the mobile user’s computer to “see” the Exchange Server much more effectively, and this should not cause problems when the user also comes into the office and connects directly to the network.

Discuss This Question: 8  Replies

 
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  • Jerry Lees
    Interesting. The only thing I can think of is that maybe she has static wins or dns entries that are presenting a problem for her. I've seen similar situations where a DC was on a 192.168.1.x/24 segment and the user was unable to authenticate because their home network was on a 192.168.1.x/24 segment and the redirector on the machine was sending the traffic to the local network rather than tunneling it to the corprate network.
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  • Laurpier
    I am having a similar problem with about 10 users. We have a Cisco 3000 concentrator , VPN client 4.6, and the laptops are running Windows XP. They can connect through the VPN with no problem, but when they open Outlook, the system hangs on "trying to connect". I can ping the Exchange server. Seems like an authentication issue but I can't find where it is. When the users connect to the network when they are in the office, there is no problem.
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  • Jpeppas
    Good Evening Have you been able to resolve this issue as we have the same happening with our own connection. Would appreciate any assistance as we have exhausted all research on the Microsoft web site
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  • Robert Stewart
    I agree with Bdinerman check the vpn dns configuration and add host files.
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  • Jpeppas
    We have checked the vpn dns configuration and all seems to be in order. Any other suggestions would be appreciated
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  • Robert Stewart
    When she is connecting to the vpn, is she using Web access to get to her email? If so make sure the vpn is pointing to the correct default gateway in order to get to the internet. In short if she is using web access through the vpn most vpn's are defaulted to not allow internet traffic. At least in XP that is. Hope this helps.
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  • Snapper70
    - make sure you have full connectivity - all other apps, pinging, etc work as anticipated? - try reducing the MTU for the VPN connection - VPN, wireless, possibly DSL keep adding to the packet size; and possibly you've exceeded the allowable frame size. Try 1100 or so rather than the default.
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  • Howedy
    I have the same thing but with LAN in some pc's connected to the LAN !
    Is it a virus attack or what?
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