Advice needed for networking multiple jails with openvpn

Greetings! I am having trouble understanding how to configure my network in the manner I desire. I googled around and searched the forums and have come across all kinds of stuff however I'm not sure what is best practice and such. I saw a lot of terms such as aliases, dummy interfaces, taps, bridges, etc.

I attached an image of what I am trying to achieve. I have a remote server with one public IPv4 address and I am trying to configure a virtual network on the server for communication across the jails and communication through a separate virtual network for management and monitoring. The management/monitoring network is to be routed through a openvpn connection. I am using pf nat and redirection to handle the link from the public ip to the jails.

I am mainly not sure how to implement this virtual network and I need advice on what tools to use. My background is in hardware and software with limited networking so I could be doing this completely wrong. Any advice is greatly appreciated.


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The way I do this is by having a single openvpn from the jail server (sita A) to Nagios (monitoring) server (site b). I have nrpe installed on the jail server, the nagios host can queries the NRPE client on the jail server which is configured to check if apache is running for example using check_http. I have one openvpn connection, 1 nrpe client monitoring all the jails and disk space on the host etc.

As for communications between the jails, as an example I have webserver01 configured on, webserver 2 on, sql server on They all have one single IP address.