Can't access server

  • Heya folks,
    I am in a bit of a pickle:
    1 pfsense server in gcloud serving as vpn server.
    1 server on-premise to serve as a web host on, let's say port 8084.
    On-premise is connected through openvpn to pfsense.

    I need to NAT from the pfsense between WAN and LAN interfaces in the pfsense.

    I have followed 5+ guides, but it just won't freaking work (a bit agitated at this point, as I've been doing this on/off for more then 2 weeks, troubleshooting and reinstalling servers for troubleshooting purposes).

    External IP is something different (
    Gcloud WAN interface is connected to address: (/24 subnet)
    Openvpn network is
    On-premise is connected on (/24 subnet)

    On-premise can ping Google and various websites, but I can't for the sake of me do a NAT between wan interface and openvpn.
    Is there anyone that can help me with this in any way shape or form?
    Even pointing me in a direction would be helpful somehow.

    Of course I am willing to provide all the logs and info that is necessary to solve this, it would mean a lot to me if this got resolved! :)

    First question that will most likely be asked:
    Why not just host the webbserver on gcloud?
    Well it can't fit within the free tier VM as it needs to connect to a SQL server as well.

  • LAYER 8 Rebel Alliance

    Did you assign the OpenVPN Interface?


  • @Rico I've assigned the ovpn adapter (named ovpns1) as a LAN interface, and I have enabled it as well.

  • LAYER 8 Rebel Alliance

    Hmmm not really sure to correctly understand your problem or not.
    You have something like this?


    So my Browser connects to your pfSense1 WAN ( and hits the Webserver ( at your pfSense2 via the OpenVPN tunnel?
    If this is what you are trying to do I suggest you to post all of your configuration via screeshots. You must have something wrong because I have stuff running like that just fine.


  • I am not good at drawing network diagrams, but I tried to draw one as good as I could :)

    Network Diagram.PNG

  • LAYER 8 Rebel Alliance

    So your on-prem Webserver is also running as OpenVPN client which is connected to your gcloud pfSense? You are only running this one pfSense? What is your OpenVPN mode?