OpenVPN Gateway is offline, but everything works
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I have an interface setup for a VPN client service (ie, all my local network traffic goes out through the VPN). The VPN interface is up and working with and address assigned to it. All this seems to be working. All my traffic shows up as going through the VPN. However, the gateway shows as offline and now working. I'm doing my best to understand that. Can anyone tell me why it is offline?
Thanks.

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Probably this, assuming you're on net30 topology which you appear to be:
https://doc.pfsense.org/index.php/Why_can%27t_I_ping_some_OpenVPN_adapter_addressesDisable monitoring for that, or make sure you have a route pushed for the tunnel network and then setup a monitor address for .1 in the tunnel network, which might work.