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I think I've figured it out. It is a problem with Microsoft's VPN client (on XP) but only when connected to an "always on" broadband connection. We maintain internal and external DNS servers, some of the machine names are the same on both lists so when I request a server that happens to be on both lists my client machine request the external (NATed) IP address.
So it's actually doing exactly what it's supposed to be doing. The problem really is the fact that we have machine names that are the same on both internal and external networks.
On the Mac, all traffic is forced through the VPN and it essentially "forgets" about the external addresses. The same with dial-up and PPPoE.
Does that make sense?
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