cr2025x1 wroteThe steps' questions are only valid when given condition is fulfilled.
And that's weird. You were able to make a site-to-site even when you used NAT on both sides? That is very weird.
You're talking about NATing packets outbound to WAN, right? If you're NATing packets going to VPN connection, well... It is just not possible as I know.
Well, however, if NAT is completely disabled then DHCP clients of the pfSense will not be able to reach the Internet, except the router itself.
I'm not sure why you'd think that. There are docs for setting up a site-to-site VPN with pfsense on both sides with NAT.
https://doc.pfsense.org/index.php/OpenVPN_Site_To_Site
Am I not understanding you right?
cr2025x1 wrote
Then I suggest another thing.
You said you can't ping to 10.0.0.1 from the server. However, the pfSense can ping the server side.
And you also said you're allowing every inbound packets. Are you saying about rules of WAN interface?
To me, it seems obvious that this is a firewall problem.
If that my guess is right, you should add the rule to LAN interface, not WAN interface, considering my experience.
And I will guess that the pfSense's 10.0.0.0/24 resides in its LAN interface, which I believe 'rl0'.
Because if I omit the whole process related to the OpenVPN tunneling, the ping request from server will first come to OpenVPN interface ovpnc1, not WAN. It will completely bypass WAN zone.
And the request packet will try to enter LAN zone, as the recipient of the packet is 10.0.0.1 and the interface with that address is in LAN zone.
But if the firewall has no rules at LAN zone to pass packets that the source of packet is 10.250.0.0/16, it will block it. I said LAN, not WAN.
https://www.dropbox.com/s/7zvsg6dpjke7y43/Screenshot_2016-03-20-13-57-26.jpg?dl=0
https://www.dropbox.com/s/67qcsa9j1u8kzxm/Screenshot_2016-03-20-14-00-03.jpg?dl=0
I tried it, even though I had a strong feeling it would not work. It may be needed at some point, but right now I can't even see pings reaching pfsense anywhere. I already checked the ovpnc1 interface for the pings from the server, and found nothing.