Sorry but I have the same issue in a fresh installation on Ubuntu Server
10.04. On server boot openvpn autostart fail, but after the login when I
run "/etc/init.d/openvpn start" it start normally. In the
/var/log/syslog it says that it can't assign the ip address to the
server. Is it possible that the tap interface isn't ready when openvpn
start?

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Network services don't start automatically at boot time
https://bugs.launchpad.net/bugs/449326
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