I'm running Shrew on Windows 2003 with the VPN server running on a
FritzBox 7230. Problem is that I always get the error "negotiation timout occurred" when trying to connect. However with the same configuration I'm
able to connect just fine from a Win XP VM running on the same PC.


Hi Lars,

WinServer2003 is not listed as a supported OS for Shrew (only Windows
2000/XP/Vista/Win7) in the documentation - so it may not be supposed to
work at all: http://www.shrew.net/software

I had the opportunity to test a 2003 VM by now (had to find the install
disk first) and it's working there as well. So while not officially
supported it works.

Sometimes Shrew can be affected by other VPNs installed on a machine.
Do you have any other VPN clients installed on the WinServer2003 OS?
Have you maybe got WinServer setup to terminate IPSec/L2TP VPNs from
clients?

I had other VPN clients but uninstalled them. Can't spot a driver or stuff
that's left over from any of them, even checked registry.

If you can, check the log output on the VPN gateway to see if the
request from the WinSvr2003 machine is even reaching the gateway.  Post
any relevant info from there to see if that helps us in any way.

Sadly Fritzbox doesn't provide that useful logging. There's nothing at all
in there for the unsuccesful connections, for the successful ones there's
"connected" and "disconnected: timeout".

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