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I have been working on migrating our OpenVPN server from Debian 5 to Ubuntu 10.04 for a couple weeks now. Went through a slew of issues, mostly having to do with being a major newb in this realm. None the less, I now have everything working great except when the server boots. OpenVPN exits after this line in the syslog:

host ovpn-server[1230]: tcp/udp: Socket bind failed on local address [AF_INET]192.168.100.5:1194: Cannot assign requested address

Where would I fix this? I figured someone here will see this and be like, "You silly newb..." Help please! :D If you need more info I will be happy to provide it, just let me know.

~placidsolace

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Additionally if I start OpenVPN manually right after boot, either from webmin or via terminal, it works fine. –  placidsolace Oct 25 '13 at 20:27
    
Could this be as simple as a conflicting DNS entry? I thought DNS auto-updated the IP for a host when changed? –  placidsolace Oct 28 '13 at 14:19
    
Okay definitely not a DNS thing, it simply won't apply the IP to the OpenVPN server. The br0 interface gets assigned fine during boot but this error happens every time. What could this be... anyone? –  placidsolace Oct 29 '13 at 15:35
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