Outlook 2007 on Windows 7, 64-bit, will not connect to Exchange Server 2003 over IPsec VPN.
It works fine locally, and if you disconnect the local connection and do NOT reboot the computer, then Outlook will connect once you establish a VPN connection.

If I reboot remotely, and then connect via VPN, I can ping by name and I can ping by IP. I have tried turning off the Windows firewall. I have tried changing the traffic from UDP to TCP. I can connect to network shares, and name resolution to other systems is working fine.

The Exchange server is not a DC.

This has only been a problem for laptops, using a software VPN client, for the past 3 months. All of the laptops are HP.
April 17th, 2013 10:29pm

Hi there,

Exchange 2003 is out of support, it is recommended to upgrade to higher version like Exchange 2010 or higher. Your understanding would be appreciated.

Just for your reference, you may try the possible resolution below:

1. Check the VPN DNS releated configuration. You might need to contact the VPN provider to for further suggestion.

2. If Outlook is connecting via RPC over HTTP, there might be a imcompatability. Try to connect via RPC to see if this works.

Hope it is hlepful.

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April 18th, 2013 9:42am

We use a 3rd party VPN Software from Logmein called Hamachi which works well , we at the moment Believe it is possibly related to the user profile . has we have one laptop now working on one Profile but not on the other.

we are going to take that further.

July 16th, 2013 4:43am

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