Pfsense Site-to-Site IPSec IKEv2 Routing

  • Hey there,

    I'm looking for advice on how to route traffic between 2 non-PfSense routers over a PfSense-to-PfSense site-to-site IPSec IKEv2 connection.

    I've achieved a site-to-site connection successfully and I have all LAN clients from both sites talking to each other.

    Site A looks like this: Internet -> WAN -> LAN -> Windows Server router at using RRAS / NAT to a switch serving (where all my Site A clients are connected)

    Site B looks like this: Internet -> WAN -> LAN -> Windows Server router at using RRAS / NAT to a switch serving (where all my Site B clients are connected)

    Right now I have full duplex connectivity between and and therefore can access everything in and can access everything in However, I cannot figure out how to get to talk to

    Any help would be greatly appreciated.

    Thank you very much

    EDIT: I'm assuming NAT and some routes need to be applied in some way but I don't know how :<

  • Are you using 24.0.x.0/24 as the local internal networks for your hosts? Fix that first, it's a mistake that will bring you tons of headaches later on…

    With that said, if I understood correctly you just need to add IPsec Phase2 settings between and on both ends of the tunnel. That's it. You cannot really route in the traditional way with IPsec tunnels.

  • Hey! Thanks for the reply. I have a couple of diagrams that I have created that might clarify. What you said basically covers it. However, I'm afraid that may not be sufficient since the LAN clients on 10.x.x.x cannot access 24.x.x.x in either sites. I can ping from 24.x.x.x to 10.x.x.x on each site, however the reverse doesn't work because because the 24.x.x.x subnet is NAT-ed by the RRAS server as seen in the diagram. (Red means no connectivity)

    And yes, I will fix the 24.x.x.x subnets to a private IP range!

    ![Internal Diagram - Page 1 (1).png](/public/imported_attachments/1/Internal Diagram - Page 1 (1).png)
    ![Internal Diagram - Page 1 (1).png_thumb](/public/imported_attachments/1/Internal Diagram - Page 1 (1).png_thumb)

  • Ok, forget what I said earlier, in this case it wouldn't work. In fact I don't think it would ever work as long as those Windows Servers are still NAT'ing traffic. This is the main problem with NAT in general, you lose end to end connectivity. I can't think of a way to make it work because the 24.x.x.x networks are completely invisible and not routeable past each NAT'ing server.

    I'm afraid you will have to redesign that a little bit in order to get rid of unnecessary address translations.
    Can't you hook up both your 24.x.x.x and 10.x.x.x networks directly to the pfSense? Why does the 24.x.x.x network have to go through the other network first? If both reach pfsense directly, it will work pretty much straight away.

    BTW, great diagram!

  • I was starting to think this was the case because I can't find anyone that will give me a straight solution lol… so a static route won't work if that's the case?

    I really wanted to leverage RRAS for routing because most of my clients rely on Windows ADs that live in both sites. I've tried creating routes and stuff but I figured my lack of success was due to my lack of networking knowledge and lack of implementation experience with routing... :(

  • Solved by removing the RRAS in between so now DHCP and NAT live on the PfSense firewalls. Thanks for the suggestion! Also no more subnets for private IPs!

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