If the wireless interface is configured as 'system-wide' in
NetworkManager the host interface will be up without a log-in and
openvpn will establish the tunnel as soon as the route appears.

If NetworkManager establishes the wireless connection after GDM log-in
the openvpn connection establishes itself as soon as the route appears.

I don't have any openvpn connections defined via NetworkManager. I have
the openvpn service defined in /etc/openvpn/connection.conf.
/etc/rc2.d/S16openvpn runs at boot-time.

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OpenVPN client does not recognize WLAN connections
https://bugs.launchpad.net/bugs/347788
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