Tunnelblick not Properly Setting up Tunnels with Two VPN Connections

[Alex Rothberg]

I have two VPN connections to networks with CIDRS of:

10.0/16

10.16/16

Either of the VPN connections works by it self but if I make both VPN connections, tunnelblick sets up the routes incorrectly:

$ netstat -nr -f inet |  grep tun
10/16              172.27.232.1       UGSc            2        0   utun0
10.16/16           172.27.232.1       UGSc            1        0   utun0

You can see that the same tunnel is being set for both.

I can manually fix the issue by running:

$ sudo route delete -net 10.16
delete net 10.16

$ sudo route add -net 10.16 -interface utun1
add net 10.16: gateway utun1

$ netstat -nr -f inet |  grep tun
10/16              172.27.232.1       UGSc            2        0   utun0
10.16/16           utun1              USc             1        0   utun1

[jkbull...gmail.com]

Tunnelblick doesn't do anything with routing; it is all done by OpenVPN. See Tunnelblick support for some links to resources for OpenVPN help.

If you can't get OpenVPN configured to do what you want, you can create a "connected.sh" script that will run automatically when a connection is made and perform the "route delete -net 10.16; delete net 10.16" ; see Tunnelblick VPN Configuration Scripts.