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I've got an odd issue when connecting outlook 2003 to my exchange server over a pptp vpn connection. The connection is sporadic, and will often jump from connected to "Trying to connect..." while still indicating that the current folder has been updated recently. Over a LAN there are no issues, but am not sure how to troubleshoot this further. I have a similar problem if I use outlook 2007.
I'm experiencing the the same problem. Would be nice if this could be resolved.
I'm not sure I can help you without more information about your configuration, but I thought I'd add mine for reference. Is your VPN connection normally stable? I've seen the same connection instability in Outlook on Windows machines so it could be related to your particular VPN configuration or your router/ISP among other things. It may not be related to Crossover.
I'm connecting Outlook 2003 successfully (and with good stability) to my Exchange 2003 server over VPN using VPN Tracker 5.4.4 to a Sonicwall, which I believe is IPSec, not PPTP. I'm using Crossover 8.0.1 on OS X 10.6.1.
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