Guide to OpenVPN for Mac OSX users with an Ubuntu Feisty Fawn server.


Before we get started, let's define a short legend for differentiating between things that need to be done on the gateway and on the client. The gateway will be your (Ubuntu) server. I myself use a VPS hosted at SliceHost. They offer some great service and have a nice community, both on their forum and on #SliceHost at FreeNode. The client is a Mac OSX machine in this case; though the instructions might be similar enough to get you up and running on any other operating system.

This is a gateway example.
Open your favourite terminal and execute:

echo 'some example text'

And if you need to edit a file, it will look like this:
## Everything noted with ## are instructional comments about what you need to do.
## Telling you for instance to:
## Comment out everything and add:

# Actual file comment.
This is some text that needed to be added.
The client example is similar, though styling is a bit different.
Open your favourite terminal and execute:

echo 'some example text'

And if you need to edit a file, it will look like this:
## Everything noted with ## are instructional comments about what you need to do.
## Telling you for instance to:
## Comment out everything and add:

# Actual file comment.
This is some text that needed to be added.

Let's get started!

Now that that's done, let's get started with the real thing!


OpenVPN on the Gateway

We'll begin with installing openVPN on the gateway:

sudo apt-get install openvpn

After that, make sure our openvpn config is always used:
## Comment out everything and add:
# Start our openvpn.conf automatically:

We'll need to edit some openvpn configuration files and generate some keys for the people we want to have access. There are some nice example configs, so we'll be using them. We'll need root access for the next dozen of instructions, so let's su and head to the openvpn config directory:

cd /etc/openvpn/
cp -r /usr/share/doc/openvpn/examples/easy-rsa/ .

Now that we got some examples to work with, let's edit them.

## Comment the line that starts with:
## export EASY_RSA
## And add this below:
export EASY_RSA=/etc/openvpn/easy-rsa/2.0

## You can also set some defaults for your certificates.
## Find the following variables and set them appropriately.
## For me I'll use the city of Amsterdam, Noord-Holland (NH) in the Netherlands (NL)
export KEY_CITY=Amsterdam
export KEY_ORG="FiXato-OpenVPN"
export KEY_EMAIL="fixato@an.example"

Time to source that information into our current shell session:

source ./easy-rsa/2.0/vars

And build the necessary certificates. (Certificate Authority, Server key, Client key and Diffie Hellman.) You can probably rename your server and client(s) however you want, but need to remember the names for later configuration. Answer yes when asked if you want to sign the certificates and want to commit them.
When it asks for a Challenge Password, you can just leave it blank and enter.
The Common Name that is asked when building a server key needs to be the same as the argument given to the build-key-server command ('server' in our example).
The Common Name that is asked when building a client key needs to be the same as the argument given to the build-key command ('client1' in our example).

./easy-rsa/2.0/build-key-server server
./easy-rsa/2.0/build-key client1

We'll copy the generated keys over when we get to the Client steps. It's time now to set up the openvpn.conf we told OpenVPN to autostart:

## Add: 
dev tun
proto tcp
## Change this port number if you want a non-standard port.
port 1194

ca /etc/openvpn/easy-rsa/2.0/keys/ca.crt
cert /etc/openvpn/easy-rsa/2.0/keys/server.crt
key /etc/openvpn/easy-rsa/2.0/keys/server.key
dh /etc/openvpn/easy-rsa/2.0/keys/dh1024.pem

user nobody
group nogroup
## Leave this as-is; it is the VPN virtual network address.


status openvpn-status.log
log-append /var/log/openvpn
#verb 3

push "redirect-gateway def1"

# Remove comment if you want lzo compression
# comp-lzo

You might want to change your port to something else, in the light of security through obscurity. If you don't want a log and status log, comment those lines out by putting a # in front of it.

If you want to use compression, remove the # in front of the comp-lzo line. I can recommend against using comp-lzo though, since in my tests it seriously slowed down the connection.
Note: if you changed the name of the server key, the cert and key files in the above config probably need to be changed too.

Now you need to enable IP-forwarding on the server.

echo 1 > /proc/sys/net/ipv4/ip_forward

This won't be remembered across reboots though, so either make an @reboot (Vixie) crontab for it, or do as I did and edit /etc/sysctl.conf

## Uncomment the line that says

If that doesn't work though, you can try adding this instead:


You can drop back to being a normal user now if you are still logged in as root. You will probably need to add some rules such as opening ports and NAT forwarding to your firewall. If you are using iptables, have a look at the iptables troubleshooting section. Since you technically set up a NAT, you will most likely need to add a NAT Masquerade rule:

sudo iptables -t nat -A POSTROUTING -s -o eth0 -j MASQUERADE

Be sure to replace eth0 with the network adapter that is used for your main internet connection. On OpenVZ hosts chances are this is venet0. OpenVZ hosts can complain about a missing kernel module if tap/tun is not enabled on the container at all.

The final step for the gateway server is to start OpenVPN:

sudo /etc/init.d/openvpn start

OpenVPN on the Client

On the client we need to install an OpenVPN client, for Mac OSX I use Tunnelblick which is currently hosted at Google code. After opening the .dmg file, copy the file to your Applications. When this is done, let's transfer the client certificates from the gateway to the client, I prefer to use SCP for this.

You will probably need root ssh access to the file. If you don't have that, make sure you've copied the keys to your homedir instead. If you have created multiple client certificates, or changed the names of the certificates, then don't forget to scp those over as well.

scp root@your.gateway:/etc/openvpn/easy-rsa/2.0/keys/{ca.rt,client1.{crt,key}} ~/Library/openvpn && sudo chown $USER ~/Library/openvpn/{ca.rt,client1.{crt,key}}

Now that we have a client, we will need to configure it. Be sure to set your Gateway server's IP where it says YOUR-GATEWAY-IP-GOES-HERE and if you also picked a non-standard port, change that in this config as well. The same applies for any client certificates you've created on the gateway.

# We are a client, not a server/gateway.

# We use a TUN interface
dev tun

# We use the TCP protocol
proto tcp

# Prevent a man-in-the-middle attack by only allowing to connect to a server which has set the server-only bit on its cert (
remote-cert-tls server

# The hostname/IP and port of the server.
# You can have multiple remote entries
# to load balance between the servers.
## If you chose a non-standard port, change 1194 to the port you picked.
remote YOUR-GATEWAY-IP-GOES-HERE 1194          

# Keep trying indefinitely to resolve the
# host name of the OpenVPN server.  Very useful
# on machines which are not permanently connected
# to the internet such as laptops.
resolv-retry infinite

# Most clients don't need to bind to
# a specific local port number.

# Downgrade privileges after initialization (non-Windows only)
user nobody
group nobody

# Try to preserve some state across restarts.

# SSL/TLS parms.
# See the server config file for more
# description.  It's best to use
# a separate .crt/.key file pair
# for each client.  A single ca
# file can be used for all clients.
## If you picked different names for your client certificates, change here
ca ca.crt
cert client1.crt
key client1.key

# Enable compression on the VPN link.
# Don't enable this unless it is also
# enabled in the server config file.
# comp-lzo

# Set log file verbosity.
verb 3

# Make sure the right gateway settings are used.
push "dhcp-options DNS"
push "dhcp-options WINS"
push "redirect-gateway"

You should now be able to start Tunnelblick. It will add a new icon to the top right of your menubar. Click on it and connect to your new VPN connection! Also check out the 'Details' options, so you can check the 'Set nameserver' checkbox.
Once you get connected, visit or and see if it reports your gateway's IP.

route -n
netstat -nr

The ifconfig should report your new tun0 device and the route/netstat commands (route for Ubuntu and netstat for OSX) should show it is routing the client's traffic through your gateway server. The ping should indicate it has access to your new tun0 via the new virtual private network.

If you have problems connecting to your gateway, or resolving DNS, be sure to check out the iptables troubleshooting guide below. You will probably need to open up your firewall for your new tun0 device.

It is wise to set up a new location profile for your OpenVPN connection, where you use static/manual settings instead of DHCP. OSX seems to prioritise the DNS settings it gets from the DHCP server over the manual DNS settings set by OpenVPN, thus kinda failing domain name lookups.

Network/DNS settings

It is advised to add external DNS servers to your Network preferences. My preference goes to OpenDNS
First open your Network Preferences: and click on the Advanced button followed by the DNS tab to get the list of DNS servers and add the OpenDNS servers (at time of writing and to it: Apply these settings and your connection, even via the OpenVPN connection, should use the OpenDNS servers for domainname-lookups.


Of course you can still encounter some issues. Here are the issues I've encountered.


If you are using IPtables, these are some rules for the gateway server that will probably help you out. I'm no expert on iptables though, so I'm not quite sure of what the risks are of adding these rules, but they were what I needed to get my VPN tunnel working without disabling all my iptables rules.

You'll most likely want to open up the openVPN port 1194:

sudo iptables -I INPUT -p tcp --dport 1194 -j ACCEPT

Since you technically set up a NAT, you will most likely need to add a NAT Masquerade rule:

sudo iptables -t nat -A POSTROUTING -s -o eth0 -j MASQUERADE

If you reject most traffic, make sure you allow input/forward/output traffic for your tun0 device:

sudo iptables -I INPUT -i tun0 -j ACCEPT 
sudo iptables -I FORWARD -i tun0 -j ACCEPT 
sudo iptables -I FORWARD -o tun0 -j ACCEPT
sudo iptables -I OUTPUT -o tun0 -j ACCEPT 

If you already have an iptables.rules file from which you automatically load your firewall rules, you can add the following before your reject all rules:

## Add to your *nat section:

## Add to your *filter section:
-I INPUT -p tcp --dport 1194 -j ACCEPT
-I INPUT -i tun0 -j ACCEPT 
-I FORWARD -o tun0 -j ACCEPT
-I OUTPUT -o tun0 -j ACCEPT

You will probably want to save your iptables rules after everything is working.

sudo iptables-save > /etc/iptables.up.rules

You can easily import these rules later with:

sudo iptables-restore < /etc/iptables.up.rules

Or add them to your network config so they are automatically reloaded:

## Add this to automatically restore your stored iptables rules when then network goes up.
pre-up iptables-restore < /etc/iptables.up.rules

Routing issues after network switching:

I've encountered some problems when switching between local networks after having had the VPN on. It seems that after I've switch to a different LAN, I can't reach the gateway host from the new local network, thus not allowing me to set up the VPN from the second VPN. My guess is that not all routes are reset after disconnecting.

I used to just reset my machine, but now found a solution that seems to work.
To find out what route seems to be incorrect use:

netstat -rn

In my case it was w.x.y.z/32, where w.x.y.z is my gateway's IP.
You can remove it via:

sudo route delete w.x.y.z/32

Contact details

@FiXato on Twitter
Other details can be found on my Google profile

References used:

Install OpenVPN on Ubuntu An old guide aimed at Ubuntu for gateway and client, which initially helped me set up my openVPN connection. Some of the instructions are either outdated or incomplete though.
OpenWRT / Firewall/Routing Issue with OpenVPN which pointed me in the direction of the tun0 rules.
UbuntuForums topic which helped me make ip forwarding on the gateway permanent.
@reboot Vixiecron rule
Tunnelblick wiki: Using Tunnelblick


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