Apple removed support for pptp as part of the iOS 10 release. Apparently pptp is susceptible to man in the middle attacks so I guess that’s a good thing. The bad thing is that OpenVPN is really really difficult to setup. You’re going to know some basic things about networking to set it up and be prepared for a lot of frustration. Here are the important parts to my setup
- DD-WRT router running build 20180 setup for internal network of 192.168.0.*
- Using Mac options (not windows)
- Connect via iPhone (same setup for iPad, have not tested via Mac yet though)
Similar to how you setup SSL certs for a web server (if you ever have done that), you’re going to have to setup keys for the server (your dd-wrt router) and your client (your iPhone, for instance). The best guide I found do this is this post from sparklabs. It will guide you to download EasyRSA and to generate your server and client keys. Be sure to save them in different directories so you don’t get confused which is which. Also ensure to rename your dh.pem file to dh2048.pem as it states in the instructions. For the client .opvn configuration, I renamed mine to match my key name: client1.opvn
Server (DD-WRT configuration)
This was a huge problem for me and nothing seemed to work right. I’m running build 20180 which seems to be buggy so I had to do a few things manually. For my setup, my local network is 192.168.0.* Notice the that the third octet is “0”. Some folks have .1 or whatever. That’s what you’ll need to change for how you have your local network setup.
When you setup your OpenVPN you need to pick your VPN subnet. I picked 192.168.66.* It doesn’t matter, I just used .66 which was in another tutorial. This means that any OpenVPN client that connects will be assigned an IP address in that range. So here we go:
- Login to your router. Hopefully you do this all the time otherwise maybe this is not for you 🙂
- Go to Services, VPN, enable OpenVPN Server. Use these options:
OpenVPN Server: Enable (duh!)
Start Type: WAN Up. (System option did not work for me and I saw some folks say WAN Up doesn’t work. It works for me though)
Config via: Config File
CA Cert, Public Server Cert, Private Server Key, DH PEM: These are the four SERVER certs you created in the previous step. You need to copy and paste the block of text that ALSO includes —BEGIN CERT… until —END CERT. Don’t leave those out (they are not comments)
server.crt has a bunch of other stuff in it. Only copy the cert stuff (again, including the —- lines)
ca.cert = CA Cert (config section in DD-WRT)
dh2048.pem = DH PEM config section
server.crt = Public Server Cert config section
server.key = Private Server Key config section
Ok, now here is the big one. Add this to the Additional Config section:
dh /tmp/openvpn/dh2048.pem #you might have dh.pem here and need to fix ca /tmp/openvpn/ca.crt cert /tmp/openvpn/cert.pem key /tmp/openvpn/key.pem keepalive 10 120 verb 9 mute 3 log-append /var/log/openvpn #this is where you can view errors/status writepid /var/run/openvpnd.pid management 127.0.0.1 5002 management-log-cache 50 mtu-disc yes topology subnet client-config-dir /tmp/openvpn/ccd script-security 2 port 1194 proto udp auth sha1 comp-lzo yes tls-server ifconfig-pool-persist /tmp/openvpn/ip-pool 86400 client-to-client fast-io tun-mtu 1500 server 192.168.66.0 255.255.255.0 route add 192.168.66.0 mask 255.255.255.0 gw 192.168.0.1 push "route 192.168.0.0 255.255.255.0" dev tun
Notice at the end I have some routes setup. These are very important because they help bridge your internal network with the VPN. Again, my internal network that connects all my computers at home is 192.168.0.* The VPN will be 192.168.66.*
Once you have that click Save and then Apply settings.
Then in DD-WRT Admin GUI go to Status, OpenVPN and see if it’s running. If you don’t see a lot of information, it failed to start. Here is how you troubleshoot that.
Use Terminal to telnet to your dd-wrt router while on your local LAN. e.g. telnet 192.168.0.1 When it asks you for your username/password, do not type “admin” as the username. Use “root”. Then use the same password you use to login via the web gui. I didn’t know that you had to use root instead of admin and that screwed me up for a little bit.
Ok, now you should be connected to your dd-wrt router. OpenVPN is probably not running but do “ps” to list all running processes. To check if openvpn is running, do “ps |grep open”. If it’s not running, then check a few things. go to your /tmp/openvpn directory. Do you see your certs there? The GUI should have the individual config sections as files. Check to make sure dh2048.pem is there and that first four lines in the Additional Config that you added above actually map to real files. If not then simply cp dh.pem dh2048.pm or change your Additional Config section to match the file name. Also look at your /var/log/openvpn log file (you can type cat /var/log/openvpn) to see if there are any obvious errors.
Try to start it manually now. Simply type “openvpn openvpn.conf” If after you hit enter and you DO NOT see a new line, then it’s running. If it immediately returns a new line, then something is still wrong and you need to look into the log file. If it DOES NOT return a new line, you can also verify it’s running in the web gui by going to Status, OpenVPN.
Now here is the tricky part, you obviously want DD-WRT to manage starting the service so try to see if it can handle it from here (assuming you got it working via the terminal). Ctrl-C and kill the openVPN that you had running in Terminal. (Check Status, VPN and you should see it not running). Now go to Services, VPN, click Disable for Open VPN, Save, Apply Settings (this should end your terminal session as the router reboots or whatever), Click Enable, Save, Apply Settings and now it should be running. If not, continue to troubleshoot as above. If you can’t get it to work in the GUI, then I would recommend just continue testing via Terminal to ensure you can the rest of it working.
Once you have it running, now you get to play with iptables! In order for the .66 OpenVPN segment to see your other computers on the network, you have to setup some rules. What does that mean? Basically in order for traffic in the .66 segment to play with your internal computers, you need to explain how they can travel there. This is what I used.
iptables -I INPUT 1 -p udp --dport 1194 -j ACCEPT iptables -I FORWARD 1 --source 192.168.66.0/24 -j ACCEPT iptables -A FORWARD -i tun+ -j ACCEPT iptables -A FORWARD -o tun+ -j ACCEPT
Let me explain what they do:
The first line ensures that your firewall does not block access to your router. We want to make sure UDP port 1194 is open. If it’s not open then the VPN will never work! To test if the port is open, you’ll need to connect from somewhere remote (after you run these commands obviously). Use nc to do this e.g. nc -vnzu 188.8.131.52 1194 Change 184.108.40.206 to your public ip address. the -u option is for UDP. If you ever wanted to test another port under TCP, just remove the u in -nvnzu Very useful!
The next three lines all allow the forwarding of those requests from your VPN into your local network.
So let’s test. Assuming OpenVPN is running, connect via terminal to your router again. check opevpn is running (ps |grep open). Ideally you check to see if your port is closed by running nc command above. Now copy and paste those iptables lines into terminal and run them all. Check again and nc should report the port is open. If openVPN is not running, copy and paste the iptables commands, verify you see them using iptables –list and then start openvpn openvpn.conf That terminal session is basically locked running openvpn. You can always start another terminal session that is looking at the log file too.
If that worked, fantastic, now you just have to get the client configured and this isn’t easy either!
It was really nice of Apple to remove PPTP support, but NOT add native OpenVPN in the Settings ! You’ll have to download a VPN client for your iPhone so go to the app store and download OpenVPN. Now this is the pain in the butt part, you have to copy your client certs (NOT SERVER!) onto your iPhone. Of course you can’t magically drag files onto your phone so you have to use our friend iTunes. To do this, connect your phone to iTunes (via cable I guess). Click on your device, click on Apps, scroll DOWN to the bottom until you see a list of apps that allow you to copy files. (This is not the section above where you can rearrange your app icons). Click on OpenVPN app and drag the 4 clients files into the right hand side Documents section (four files = ca.crt, client1.crt, client1.key, client1.opvn). Sync. If you can’t find where to copy the files, SCROLL DOWN to the bottom of the Apps section of your phone.
Open OpenVPN on your iPhone and you should see a configuration for the public ip address of your OpenVPN server. If you screw up, you can delete it by touching on the ip address, upper right hand corner touch Delete, touch red circle on the left with the line through it (very bad UI experience). Before you connect to your VPN, ensure to turn off Wifi on your iPhone otherwise it’s not a very good test (I don’t think it will work anyway!) To test connected to your OpenVPN, slide the button to the right (again very bad UI design). You should see it say Waiting for server, Connecting, Connected! Down below in VPN IPv4 section you should see the IP address that was assigned. For me it’s 192.169.66.X If you are not connected, then touch the “Connecting” section of the app to read the log. Initially when I set it up, there was a time difference between where I setup the cert and GMT. I had to wait 5 hours for it to be resolved. There is a way to fix it, but since I was already going to sleep the problem worked itself out the next day ;-). To manually check this look at your clien1.crt file. There is a Validity section which helps you understand when the cert STARTS working and when it ends (in 10 years).
If all that worked, now you can see if you can access anything in your home network. You can try to use VNC Lite to connect to a home computer or download the Ping app from the app store and ensure you can see your local network. I assume there is something you want to VPN in for so test it. You can also test to ensure you are connected by pinging the IP address of your phone. For example, from a computer on my local network, ping the IP address that your phone was assigned. e.g. ping 192.168.66.2
If that all works, you’re almost there. If you reboot or change your configuration on your router, your iptables commands get lost. To make them permanent, go to the dd-wrt gui, click administration, commands. Copy and paste those iptables runs and click Run Commands and to save permanently click “Save Firewall”. That’s it!
Phew. I hope that’s it and you get this working. The certs are tricky as well as the routing and firewall rules. All this info was build from various sources. Here are those sources just in case there are some variations to your setup. Good luck!