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Configuring a Site-to-Site PKI (SSL) OpenVPN Instance

This how-to covers how to setup OpenVPN using Site-to-Site PKI (SSL). For users who want to make a hub-and-spoke multi-site setup, as opposed to a mesh, this method may be a good fit.

One pfSense® router is the server and the others are clients. The primary/main office is typically the server, but whichever site has the most bandwidth and fastest firewall may be the best choice.

Generate keys/Certificates

This how-to article will be using pfSense software for the PKI infrastructure. If there is already an existing infrastructure or do not wish to use pfSense software for this task, existing certificates may be used or generated elsewhere. CAs/Certificates generated outside of pfSense software must be imported into pfSense.

The CA and Certificates may be created under System > Cert Manager from the pfSense webGUI, or use certificates made with the OpenVPN wizard. The certificates are stored in config.xml, so a normal configuration backup will keep them safe.

Ensure there is one CA, one Server Certificate, and one User certificate for each client site. For the Common Name of each certificate, use the hostname of the firewall or some other easily distinguishable unique name for each site.

Server Setup

The bulk of the OpenVPN server setup is fairly straightforward, similar to that for a remote access setup.

  • Server Mode: Peer to Peer (SSL/TLS)

  • TLS Authentication: Check box boxes

  • Peer Certificate Authority: The CA created in the cert manager

  • Server Certificate: The Server certificate created in the cert manager

  • IPv4 Tunnel Network: An unused subnet. When using subnet topology, OpenVPN will assign one address out of this pool to each client. When using the older “net30” topology, OpenVPN will carve /30 networks (4 IP addresses each) for each client connection out of this network. Make sure this network is large enough to handle all of the clients. With net30 allocations, a /24 will fit 63 clients (64 total /30 entries, but the server itself uses the first.)

  • IPv4 Local Networks: Local subnet that clients can access here at the server location. Additional local subnets may be added, separated by commas.

  • IPv4 Remote Networks: A comma-separated list of all the remote client LAN networks (e.g.,

Finish the Server Configuration

Look over the settings, and adjust any other required settings, such as the Encryption Algorithm, Compression, etc.

Press Save when done.


In order for the server to reach the client networks behind each connection, both a route to the network (IPv4 Remote Networks entry) to tell the system that OpenVPN knows about that network, and also an iroute that tells OpenVPN to which specific connection a subnet belongs.

To add an iroute, visit VPN > OpenVPN on the Client Specific Overrides tab.

Add an entry for each client, and on each one:

  • Set the Common Name field to the name of the certificate for the site

  • On pfSense software version 2.2, use the IPv4 Remote Network/s here on the Client Specific Override to add iroute networks.

  • On older versions of pfSense software, in the custom options/advanced box, add an iroute statement for the client network:

    iroute a.a.a.a b.b.b.b;

    Where a.a.a.a is the subnet’s starting IP, and b.b.b.b is the subnet mask.

Firewall Rules

Be sure to add firewall rules under Firewall > Rules, on the OpenVPN tab.

Also add a firewall rule on WAN to permit traffic to the OpenVPN port configured for the server.

Client Setup

Export the CA certificate only (not the CA key), along with the client certificate and client key for this site. Import them into the client firewall under System > Cert Manager.

For the client VPN configuration:

  • Server host or address: The server’s IP address

  • Server port: The server’s OpenVPN port.

  • TLS Authentication:

    • Check Enable authentication of TLS packets.

    • Uncheck Automatically generate a shared TLS authentication key.

    • Copy/Paste the TLS shared key from the server configuration.

  • IPv4 Tunnel Network should be left blank

  • Peer Certificate Authority: The CA imported to the cert manager

  • Client Certificate: The User certificate imported to the cert manager

  • Use the same Protocol, Encryption Algorithm, and Compression settings as chosen on the server.

Finish Up

Save the client configuration. It will attempt a connection to the server. If it does not connect immediately, check the logs under Status > System Logs on the OpenVPN tab on both the client and server firewalls.