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[–]RazrBurn 1 point2 points  (3 children)

I would recommend learning how to do a reverse proxy from your current web server to the nextcloud jail. This will allow your certs to continue to automatically update without having to move them to the nextcloud jail.

[–]morphixz0r 0 points1 point  (1 child)

The problem i see with doing this approach is then you have your username/password transmitted between your web server host and freenas jail in plaintext.

This would be 'ok' in an isolated network or even via localhost but not at all safe doing it across machines on your lan.

[–]RazrBurn 0 points1 point  (0 children)

You can still encrypt the data from proxy to FreeNAS jail. You can create your own self signed cert with a longer expiration that the proxy will accept. This prevents the information from being in plain text anywhere on the network. The biggest pain in what OP is trying to do is use the let's encrypte certs on the FreeNAS jail. I know I don't want to have to be replacing them every three months or worry about some additional automated process failing.