It's running on a Dell R720 and wanted to give myself room to play with other VMs because I don't want the whole server to be for TrueNAS. 2 x E5-2697 v2, 128 GB RAM, and 8 x 3 TB SAS HDD in RAID 10 is way too much for my TrueNAS needs.I did not realize that you were running TrueNAS as a VM; there is likely some configuration in there that needs to be fixed (unfortunately I know little about that end of things). As a general rule I would recommend that anytime you want to go beyond a simple file server you should run on bare metal and even then probably not something you should do.
The thing is, I don't understand why your script won't get any connection at all but I can install a plugin just fine, the only issue is that the jail will lose connection / DNS after OpenVPN is connected on it.
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Even on my old server that has a transmission plugin jail with OpenVPN running fine on, I can't recreate it in a new jail, the same issue happens when OpenVPN is connected.
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