For a while I've noticed that if VPN dies while connected (eg. If you put your computer to sleep before disconnecting) it won't reconnect until after a reboot.
I checked routing tables and logs etc with little success and I JUST realised that when it starts 'racoon' (a key management daemon) starts up. A stale racoon process causes issues when trying to connect hence if you kill it first then try and connect it works fine.
Something like this should do it (from terminal):
sudo kill `ps -U root -o "pid,comm"|grep racoon|cut -d" " -f1`
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