macmacosnetworkingvpn
I'm using OSX Mavericks at the moment. Looking through VPN options (L2TP in my case), I see that it is possible to "Send all traffic over VPN connection".
However, I cannot figure out if I don't click it, what traffic goes through the VPN connection and what doesn't? Can I specify this? And if I do click it, does it mean that even local subnet traffic goes through this VPN connection?
More generally, I'm really trying to figure out what this checkbox means.
I think, for what you want to do, you can use the Proxy Switchy! extension for Chrome and create a different profile for your VPN and set the Network in the Proxy Switchy! settings as so:
This seems to be the easiest way to achieve what you want as selecting a profile will route through that specific connection.
All your other traffic will be routed through whatever the local connection is, and your Chrome traffic will be routed through the VPN.
You can enable that feature on OS X by going to:
System Preferences → Network → Your VPN Connection → Advanced → Send all traffic over VPN
On your Windows 7 box you can go to:
That should make it so all traffic is sent over the VPN on both systems.
Best Answer
From Mavericks help:
For a real world example, if you had a VPN setup to tunnel to your corporate network over the Internet, the VPN would only send 'intranet' traffic over the VPN tunnel. So for example, if you wanted to access http://mycompany.intranet/ this would send packets over the VPN, but accessing http://apple.com would happen outside of the VPN.
By clicking the checkbox, all traffic would go through the VPN tunnel. In practice you may not want your personal traffic (webmail, personal web browsing etc) to go through your company VPN as it would most likely be logged and it may also be slower than just using your raw internet connection.