Using OS X's VPN connection from Windows Guest

[nikster]

Hi,

The reason I bought VMWare Fusion back when was that the NAT worked the way I thought it would work: The VM would simply use the OS X host's internet connection. If VPN was on on OS X, it would be on in the Windows guest.

But something recently broke this for WiFi. When I connect to VPN on OS X over WiFi, then try to access our internal networks from the Windows guest(s), it doesn't work.

Strangely, this is only for WiFi. When I am connected to VPN over iPhone tethering, the windows guests see the VPN just fine.

Anybody has any ideas on this? It used to work over WiFi too. It's rather inconvenient as it is. I changed the network interface order so that the VPN is on top, but that didn't help either.

Thanks for any ideas...

[ColoradoMarmot]

Interestingly, we've just confirmed a new apple bug with the VPN - the racoon process get's hung on disconnects at times.  If you go into finder and do:

cd /user/sbin

sudo ./racoon

It'll let you reconnect.  Don't know if it's related.

One idea - have you tried pinging an IP address on the private network inside the VM?  If that goes through, it may be a DNS issue.

[nikster]

You're right, it *is* DNS!

I can't believe I never tried this! What a brilliant idea.

So yeah it's DNS. I can access the same site that doesn't work using the name using its IP address (which I get from OS X by just pinging the server).

So DNS works on the OSX side, but not on the VMWare Fusion side / Windows client. And it's only sometimes, as sometimes it seems to be OK

Again let me know if there's anything I can do to debug this because a DNS issue might very well be very specific to my company VPN configuration. Our company VPN has a lot of DNS issues on the OS X side and I had to add many servers to my (OS X) hosts file to make things work. 

The particular site I am trying to access works fine in OS X, and doesn't need an entry in my hosts file, however. So I could try two things - add the server to my OS X hosts file which shouldn't do anything but who knows.

And add it to the Windows hosts file as a workaround.

PS: I tried ipconfig /flushdns in the windows client to no avail - this is failing at some other level.

[ColoradoMarmot]

We have the same issue sometimes - I just manually add the company DNS servers to the config inside the VM - it's brute force, but then everything works.

This might also explain why it changes between airport and LAN - do you have the same DNS settings on the host for both?

[nikster]

Another update: It's a non-issue with the new VPN server / connection we are now using at the company. This new VPN forces all traffic over the VPN, whereas the old would allow OS X to bypass the VPN for non-VPN sites. The old one also had DNS issues on the OS X side which were resolved by adding entries to the hosts file.

Our new VPN has no DNS issues on the OS X side, and works perfectly on the Windows guest as well.

So the VPN before was a bit wonky - the only fault I can perhaps see with VMWare is that it seems to ignore the entries in the Mac OS X .hosts file.