Tag Archives: openvpn

Fix no internet in pfSense OpenVPN

I came across an issue with pfSense where I had created an openVPN connection but it would not work with internet traffic. The VPN connection established fine and I could connect to all internal hosts, but all internet traffic simply didn’t work. I checked the firewall logs and there were no firewall denies.

After scratching my head for a while I came across this post which suggests it might be due to the fact that there was no outbound NAT defined for the VPN network I created.

I went to Firewall / NAT / Outbound and sure enough, there was no outbound NAT rule for my VPN network. I manually created it for my VPN network and voila! Internet over the VPN!

Fix pfSense OpenVPN unable to bind to VIP issue

A while ago I bought multiple static IP addresses from my ISP. I configured the IPs as Virtual IP addresses through Firewall / Virtual IPs. Everything was dandy.. until I tried to assign OpenVPN to listen on one of my new IP addresses. No matter what I tried I could only get it to work if it listened on my gateway IP.. none of my other static IP addresses would work. The GUI would let me save the configuration, but if I headed over to Status / Openvpn I would see the following:

[error] Unable to contact daemon Service not running?

Digging further in the logs by going to Status / System Logs and then selecting the OpenVPN tab revealed the following snippet:

Time Process PID Message
May 15 19:42:00 openvpn 73195 Exiting due to fatal error
May 15 19:42:00 openvpn 73195 TCP/UDP: Socket bind failed on local address [AF_INET]<redacted>:443: Can’t assign requested address

After much digging I finally stumbled upon this post in the pfsense threads. In it they mention that in the Firewall / Virtual IPs screen not to bind  (in the interface option) your IP addresses to the WAN interface, but rather to bind them to localhost. That did the trick!

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!

Updated crouton OpenVPN script

Updates to Chrome OS have broken the VPN script I had for crouton. I had to tweak a few things including a default route for my VPN server so that broken VPN connections could automatically reconnect.  I had to work around another new security feature:  selinux denying sed the ability to create temp files in /etc. The updated script works well, though… until Google updates ChromeOS again 🙂

See this post for instructions on how to implement the script.

Here it is:


VPN_SERVER=$(cat $CONF_DIR/$CONF_FILE | grep remote | awk '{print $2}')
DEFAULT_GW=$(sudo route | grep default | awk '{print $2}' )

cd "$CONF_DIR"

# Add google DNS on top of current ones, since openvpn command does not do it
sudo cp /etc/resolv.conf /tmp/resolv.conf
sudo sed -i "1s/^/# new DNS\nnameserver $DNS_SERVER\n# old DNS\n/" /tmp/resolv.conf
sudo cp /tmp/resolv.conf /etc/resolv.conf

sudo openvpn --config "$CONF_FILE" --dev tun0

# When ctrl-c is hit remove tun0 and cleanup the DNS
sudo openvpn --rmtun --dev tun0
sudo cp /etc/resolv.conf /tmp/resolv.conf
sudo sed -i '/# new DNS/,/# old DNS/d' /tmp/resolv.conf
sudo cp /tmp/resolv.conf /etc/resolv.conf
trap 2

Connect Linux OpenVPN client to Netgear VPN Server

My parents got a shiny new Netgear R80000 wireless router which supports OpenVPN out of the box. The client configuration it generates doesn’t work right away, though, when I try to connect from my Linux Mint desktop. The connection is successful but I can’t ping or reach anything on the other network.

I discovered on this forum that you must add a couple options to the config file the router produces. You can do this either on the command line or by modifying the config file. The options are to add an interface to the VPN and to  create a route to the network, like so:

--ifconfig --route

I took the generated non-windows VPN configuration from their router, unzipped it on my linux desktop, and then ran this command:

sudo openvpn --config parents.ovpn --ifconfig --route

It worked like a charm.

Use OpenVPN from within crouton chroot

Update: Google released a ChromeOS update that broke the openvpn script. Find the updated version here.

Update 3/29/17: Added a DNS suffix line to fix broken DNS

I posted a little while ago about how to get openvpn working on your chromebook. That guide required that you run openvpn outside your chroot on the chromebook instance itself.

Lately I’ve been really feeling the need to have openvpn run within a crouton chroot instead. The solution is to take the script from the post above and divide it into two parts. One part you will still have to run outside your chroot but you will only have to do it once on each reboot. The other part can safely live inside your chroot.

First, on your chromebook itself (not in a chroot) make a small script to tell the shill service not to kill tun0:

sudo echo "

#Allows the tun0 device to function
sudo stop shill
sudo start shill BLACKLISTED_DEVICES=tun0" > /usr/local/bin/shill

chmod +x /usr/local/bin/shill

Next, create this script within your chroot. Be sure to modify the environment variables to suit your setup.



cd "$CONF_DIR"

# Add google DNS on top of current ones, since openvpn command does not do it
sudo sed -i "1s/^/# new DNS\nsearch $SEARCH\nnameserver $NAMESERVER\n# old DNS\n/" /etc/resolv.conf

sudo openvpn --config "$CONF_FILE" --dev tun0

# When ctrl-c is hit remove tun0 and cleanup the DNS
sudo openvpn --rmtun --dev tun0
sudo sed -i '/# new DNS/,/# old DNS/d' /etc/resolv.conf
trap 2

Voila, we now have openvpn working inside our chroots again.

Fix openVPN on chromebooks

Edit: I’ve updated the script due to more updates in ChromeOS. Find the update here.

Around October of 2015 an update came out to Google Chromebooks that had an unfortunate side effect for me: openvpn no longer worked. Despite my having created a tunnel device seconds earlier, openvpn complained that a tunnel device didn’t exist.

I finally found a fix for this here. It turns out that the update caused the “shill” process to aggressively kill the tun0 interface. The clever workaround as posted by pippo0312 works flawlessly. It involves creating the openvpn tunnel in chromium itself rather than in a crouton chroot as I had previously done.

The original script took an argument for an ovpn file to use. Since I only have one VPN profile I just modified it to specify the ovpn file I use.

Place the script in /usr/local/bin on your chrome install (not a chroot) and mark it executable by issuing chmod +x

#!/bin/sh -e
trap '' 2
# Stop shill and restart it with a nicer attitude towards tun0
sudo stop shill
sudo start shill BLACKLISTED_DEVICES=tun0
# Sleep 10 seconds to allow chromebook to reconnect to the network
sudo sleep 10
sudo openvpn --mktun --dev tun0
sudo sleep 3
# Add google DNS on top of current ones, since openvpn command does not do it
sudo sed -i '1s/^/# new DNS\nnameserver\nnameserver\n# old DNS\n/' /var/run/shill/resolv.conf
# Lauch openvpn, finally...
sudo openvpn --config $1 --dev tun0
# When ctrl-c is hit remove tun0 and cleanup the DNS
sudo openvpn --rmtun --dev tun0
sudo sed -i '/# new DNS/,/# old DNS/d' /var/run/shill/resolv.conf
trap 2

Now you can just issue the command of the name of your script and vpn works again! hooray.

Configure full VPN tunnel in Sophos UTM

For years now I have had a successful split tunnel VPN with my Sophos UTM. Recently I’ve wanted to have a full tunnel option for greater security in remote areas (hotel wi-fi, etc.) Unfortunately setting up such a thing in Sophos is NOT straightforward.

The biggest problem I had was that no websites would work after the VPN was initiated. NSlookup was fine, connection was fine, even internal sites would load properly, but no external internet.

Thanks to this post I finally found the culprit: the pesky allowed networks feature for each UTM function. In my case, the VPN was allowing all the necessary traffic through but my transparent proxy was denying web access. I had to add my VPN pool to the list of allowed networks to my proxy.

To summarize, this is what you must do to have a full VPN tunnel:

  • Configure the desired method in the Remote Access section. Take note of whatever IP pool you use for your VPN. In my case I used VPN Pool (SSL)
  • Ensure that internet access is in the list of allowed networks for the user you’ve configured for VPN (Any, or Internet IPv4/6)
  • Add your VPN pool to the list of allowed networks for each service you use.
    • Network services / DNS
    • Web Protection / Web Filtering
  • Profit