Site to site VPN between pfSense and DD-WRT

I’ve been trying to establish a site-to-site VPN connection between my house and my parents’ for a couple years now. Each time I try I become frustrated and eventually give up. No longer! I’ve finally gotten a site to site VPN working between my pfSense router and my parents’ Netgear Nighthawk R8000 running DD-WRT v3.

It was quite the undertaking for me to get these two systems talking. I drew a lot of inspiration from here. In order to get this to work you need to keep these things in consideration:

  • Protocol, port, device type, encryption cipher, hash algorithm, TLS authentication, and certificate settings all need to match
  • VPN IP addresses need to be assigned to both the server and the client
  • Routes for each network need to be established on both devices
  • Firewalls need to be configured to allow traffic to/from each network through the VPN tunnel

I used the following settings to get things working between these two devices:

OpenVPN Server (pfSense)

If you haven’t already, generate a certificate authority and server certificate. Do this in System / Cert Manager and click Add. When generating the certificate make sure the Certificate Type is Server Certificate.


  • Server mode: Peer to Peer (SSL / TLS)
  • Protocol: UDP
  • Device mode: tap

Cryptographic settings

  • Enable authentication of TLS packets: checked
  • Automatically generate a shared TLS authentication key: checked
  • Peer certificate authority & Server Certificate:  Select appropriate CA / certificate from the dropdowns here
  • DH Parameter length: 2048
  • Encryption algorithm: AES-256-CBC
  • Auth digest algorithm: SHA256 (256 BIT)
  • Certificate depth: One (Client + Server)

Tunnel Settings

  • IPv4 Tunnel network: Enter a unique (not existing on either netwonk) network here in CIDR format, ex
  • Ipv4 Local Network(s): Enter the networks you would like the remote network to access
  • IPv4 Remote Network(s): Enter the networks you would like the local network to access
  • Compression: Enabled with Adaptive Compression

Advanced Configuration

Optional? I found that for some reason the routing table wasn’t properly populated with the remote network on my pfSense server. I added a custom option to take care of that:

route <remote network> <remote subnet mask> <remote VPN IP>

In my example it ended up being “route”

Key export

You will need to export the Certificate Authority certificate as well as the client certificate & private key files for use with dd-wrt. Do this by going to System / Cert Manager. There are little icons to the right of the certificates where you can click to download them.

Export the CA certificate as well as both the certificate and key from whatever was specified in the Server Certificate section from the above OpenVPN configuration.

OpenVPN client (dd-wrt)

Go to Services / VPN and look for the OpenVPN Client section

  • Start OpenVPN Client: Enable
  • Tunnel Device: TAP
  • Tunnel Protocol: UDP
  • Encryption cipher: AES-256 CBC
  • Hash Algorithm: SHA256
  • User Pass Authentication: Disable
  • Advanced Options: Enable
  • LZO Compression: Adaptive
  • NAT: Enable
  • Firewall protection: Disable
  • Bridge TAP to br0: Enable
  • TLS Auth Key: <Paste the contents of the “Key” section under pfSense’s Cryptographic settings area of the OpenVPN server configuration>
  • CA Cert: <Paste contents of downloaded CRT file from pfsense’s CA>
  • Public Client Cert: <Paste contents of downloaded CRT file from pfsense’s certificate section>
  • Private Client Key: <Paste contents of downloaded .key file from pfsense’s certificate section>

IN THEORY this should be all that you have to do. The tunnel should establish and traffic should flow between both networks. Sadly it wasn’t that simple for my setup.


One-way VPN

After setting up the tunnel I saw everything was connected but the traffic was unidirectional (remote could ping local network but not visa versa.)

On the pfsense router, I ran

netstat -r | grep 192.168

(change the grep to whatever your remote network is)

I noticed that there were no routes to the remote network. To fix this I appended a server option in the OpenVPN server config (adjust this to match your networks)


Blocked by iptables

Adding the route on the server helped but things still weren’t getting through. I enabled logging on the DD-WRT side, consoled into the router, and ran the following:

watch -n 1 "dmesg | grep 192.168.98"

This revealed a lot of dropped packets from my OpenVPN server’s network. After a lot of digging I found this forum post that suggested a couple custom iptables rules to allow traffic between the bridged network and the OpenVPN network (adjust interface names as necessary)

iptables -I FORWARD -i br0 -o tap1 -j ACCEPT 
iptables -I FORWARD -i tap1 -o br0 -j ACCEPT

This doesn’t survive a reboot, so you’ll want to enter those two commands in the Administration / Commands section of the dd-wrt web configuration and click “Save Firewall”


Finally, after a custom routing rule on the pfsense side and a custom iptables rule on the dd-wrt side, two way VPN has been established!

CentOS7, nginx, reverse proxy, & let’s encrypt

With the loss of trust of Startcom certs I found myself needing a new way to obtain free SSL certificates. Let’s Encrypt is perfect for this. Unfortunately SophosUTM does not support Let’s Encrypt. It became time to replace Sophos as my reverse proxy. Enter nginx.

The majority of the information I used to get this up and running came from digitalocean with help from howtoforge. My solution involves CentOS7, nginx, and the let’s encrypt software.

Install necessary packages

sudo yum install nginx letsencrypt
sudo firewall-cmd --add-service=http --permanent
sudo firewall-cmd --add-service=https --permanent
sudo systemctl enable nginx

Inform selinux to allow nginx to make http network connections:

sudo setsebool -P httpd_can_network_connect 1

Generate certificates

Generate your SSL certificates with the letsencrypt command. This command relies on being able to reach your site over the internet using port 80 and public DNS. Replace arguments below to reflect your setup

sudo letsencrypt certonly -a webroot --webroot-path=/usr/share/nginx/html -d -d

The above command places the certs in /etc/letsencrypt/live/<domain_name>

Sophos UTM certificates

In my case I had a few paid SSL certificates I wanted to copy over from Sophos UTM to nginx. In order to do this I had to massage them a little bit as outlined here.

Download p12 from Sophos, also download certificate authority file, then use openssl to convert the p12 to a key bundle nginx will take.

openssl pkcs12 -nokeys -in server-cert-key-bundle.p12 -out server.pem
openssl pkcs12 -nocerts -nodes -in server-cert-key-bundle.p12 -out server.key
cat server.pem Downloaded_CA_file.pem > server-ca-bundle.pem

Once you have your keyfiles you can copy them wherever you like and use them in your site-specific SSL configuration file.

Auto renewal

First make sure that the renew command works successfully:

sudo letsencrypt renew

If the output is a success (a message saying not up for renewal) then add this to a cron job to check monthly for renewal:

sudo crontab -e
30 2 1 * * /usr/bin/letsencrypt renew >> /var/log/le-renew.log
35 2 1 * * /bin/systemctl reload nginx

Configure nginx

Uncomment the https settings block in /etc/nginx/nginx.conf to allow for HTTPS connections.

Generate a strong DH group:

sudo openssl dhparam -out /etc/ssl/certs/dhparam.pem 2048

Create SSL conf snippets in /etc/nginx/conf.d/ssl-<sitename>.conf. Make sure to include the proper location of your SSL certificate files as generated with the letsencrypt command.

ssl_certificate /etc/letsencrypt/live/;
ssl_certificate_key /etc/letsencrypt/live/;
ssl_dhparam /etc/ssl/certs/dhparam.pem;

Here is a sample ssl.conf file:

server {
        listen 443;

        ssl_certificate /etc/letsencrypt/live/<HOSTNAME>/fullchain.pem;
        ssl_certificate_key /etc/letsencrypt/live/<HOSTNAME>/privkey.pem;
        ssl_dhparam /etc/ssl/certs/dhparam.pem;

        access_log /var/log/<HOSTNAME.log>;

        server_name <HOSTNAME>;

        location / {
                proxy_set_header Host $host;
                proxy_set_header X-Real-IP $remote_addr;
                proxy_set_header X-Forwarded-For $proxy_add_x_forwarded_for;
                proxy_set_header X-Forwarded-Proto $scheme;

                proxy_pass http://<BACKEND_HOSTNAME>/;


Redirect http to https by creating a redirect configuration file (optional)

sudo vim /etc/nginx/conf.d/redirect.conf
server {

        location /.well-known {
              alias /usr/share/nginx/html/.well-known;
              allow all;
	location / {
               return 301 https://$host$request_uri; 


Restart nginx:

sudo systemctl restart nginx


HTTPS redirects always go to the host at the top of the list

Solution found here:  use the $host variable instead of the $server_name variable in your configuration.

Websockets HTTP 400 error

Websockets require a bit more massaging in the configuration file as outlined here. Modify your site-specific configuration to add these lines:

# we're in the http context here
map $http_upgrade $connection_upgrade {
  default upgrade;
  ''      close;

server {     proxy_set_header Upgrade $http_upgrade;
    proxy_set_header Connection $connection_upgrade;


Fix FreeNAS multipath error with USB drives

I have a Mediasonic 4 bay USB drive enclosure plufgged into a FreeNAS system as a backup. This enclosure randomizes hardware ID information which  confuses FreeNAS. The main symptom of this is the error message about multipath not being optimal.

The way to fix this is do drop to a command line and destroy the mistaken multipath configuration (thanks to this site for the information)

For Freenas 9.x:

gmultipath destroy disk1 disk2 disk3

For FreeNAS Corral it’s a bit different. You have to brute force remove the kernel module for multipath (thanks to this site for the explanation)

mv /boot/kernel/geom_multipath.ko /boot/kernel/geom_multipath.ko.old

Keep in mind that you may have to do this after each update.

An additional problem is that for some reason GUI doesn’t see the drives but the OS does. If you want smart checking on those other drives you have to do a bit of hackery by creating a SMART job for the visible drives, then manually dropping into a shell to add the invisible ones. Below are my notes for when I did this (I’m not sure these changes survive a reboot)

sudo vi /etc/local/smartd.conf
/dev/da2 -a -n never -W 0,0,0 -m root -M exec /usr/local/www/freenasUI/tools/sma -s S/(01|02|03|04|05|06|07|08|09|10|11|12)/../(1|2|3|4|5|6|7)/(00)

ps aux|grep smartd

kill -9 (pidof smartd)
sudo /usr/local/sbin/smartd -i 1800 -c /usr/local/etc/smartd.conf -p /var/run/