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How To Set Up a VPN Server Using a Mac

These instructions may seem arcane and complex but they’re really easy if you just follow along step by step. Donald Burr of Otaku No Podcast (otakunopodcast.com) created all of these instructions in text form, Allison just created the ScreenSteps tutorial!

I’ll be focusing on using a Mac on your home network using an Airport Extreme Router (of course any router will work but the screenshots will be for the Airport). If you have a router capable of installing the Tomato Router Firmware, you should look at Donald’s full instructions because you may not need to use a Mac at all for this, your router can do it all. See Donald’s notes for other options.

Read Donald’s instructions ===> here.

If you’d rather download this manual for easy off line reference, click here.

If you’ve installed the VPN Server but would like to UNinstall it, click here for instructions.
If you can connect to your VPN server but can’t get outside your network, click here.

Let’s get started already!

SECTION 1 – Setting Up a Static IP for the Server on the LAN Side

These instructions should be completed on the machine that will become the VPN server.

Open Network Preferences

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Select Advanced

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Copy the Mac Address

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Open AirPort Utility

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Click on your router, in my case it’s called White Dart.

Select Enter Router Password

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Enter your password when prompted and click OK.

Select Edit

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Select the Network Tab and Click the + Button

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Paste in the Mac Address You Copied Earlier

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Select Update

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Select Continue

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Quit Airport Utility when this operation completes.

SECTION 2 – Creating Account at No-IP.com

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Navigate to http://www.noip.com and select Sign Up.

Create a Username and Password

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Enter your Email address. Note the host name shown which is free, but if you want to pay you can get more options. Scroll down to the bottom of the page.

Select Sign Up

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Email Confirmation Will be Sent

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Click the Link in the Email

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Download the Update Client

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This client will run in the background and check to see if your IP address has changed, and if it has, will send it to no-ip.com

Download and Install the Client

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Enter Your No-iP.com Account Info You Just Created

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This menu should pop up automatically.

Click OK

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Click on Hosts and Check the Box Next to the Host Name You Chose

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It may take a few moments for the host name you selected at no-ip.com to show up. Make sure you note this name, you’ll need it later.

Select Update Now

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Turn on the Daemon

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I chose this rather than running the application in the background all the time.

SECTION 3 – Installing Xcode and Running Command Line Tools

Find Xcode in the Mac App Store

Install Xcode

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Install Java

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Xcode only installs the standalone Java, and it does NOT include the Java Web plugin that has been the subject of so many security vulnerabilities lately.

Select Install Next to Command Line Tools

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Wait till the installation finishes and quit X-Code

Type xcodebuild -license to Open the License Agreement

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Start Hitting the Space Bar to Scroll Through the EULA – A LOT of Times

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Type Agree

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Type agree

Joy of Agreement

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SECTION 4 – Installing MacPorts

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Navigate to https://distfiles.macports.org/MacPorts/ and scroll to the bottom to download the installer file for your OS.

Install MacPorts

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Enter These Commands in the Terminal

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To run the self update to Macports enter:

  source ~/.profile
then
  sudo port -v selfupdate

and enter your administrator password

Success

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Open the VPN Software

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Enter

  sudo port -v install openvpn2

and watch a lot of glop go by…

SECTION 5 – Installing Tuntap Drivers

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Download tuntap drivers from http://tuntaposx.sourceforge.net/download.xhtml

Open the Package File (in the folder after tuntap expands)

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Gatekeeper won’t let you just double click on the installer package (it will complain that it is from an unknown source), you have to right click on the installer package and choose “open”.

SECTION 6 – Donald’s Nifty Scripts of Doom

Download Donald’s scripts from: https://www.dropbox.com/s/4yhc5oimze9zzij/openvpn-mac.tar.bz2?dl=0

Type These Commands to Unarchive the Scripts

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cd ~/Downloads
tar xvjf openvpn-mac.tar.bz2

Setting Up OpenVPN Server

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We’re now going to run Donald’s scripts. Enter this command:

  cd openvpn-mac && sudo bash setup-openvpn-server

Name your Server (I’ve entered kyles-mac-vpn)
Enter the dynamic dns host name you noted back on no-ip.com (you DID note it, right?)

Keep Answering Questions

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The first time through you need to answer these. These steps will be duplicated MANY times, but after this the answers will be there and you can simply hit Enter for each questions.

Hit Enter for All These Questions for an RSA Key

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And Again for Some Reason

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Keep Answering…

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And Again

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And Again…

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Whew!

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Enter passphrase and password as many times as they ask for it!

Finder Window Opens Showing config-files

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Copy this file to Dropbox. It will be the first connection file you test. It would be good to name it something associated with the device on which you’ll use it (you’ll be creating one of these for each of your devices).

Create a New VPN Connection Document for Each Device You Have

In Terminal, enter: 

  sudo setup-openvpn-client connection-name

where connection-name means something to you for each different device you’ll want to connect to the VPN server. Move each of these files to Dropbox to be picked up on your devices.

SECTION 7 – Opening up UDP Port 1194

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Open Airport Utility again, select your Airport again, Select Edit again. Select the Network tab, and select the + under Port Settings

Enter Information As Shown

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Select Update

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Wait until your Airport updates.

SECTION 8 – Install VPN Software on iOS

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Download OpenVPN Connect from the iTunes App Store.

Open Dropbox

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Find the file you created and moved into Dropbox and tap on it.

Select the Open In Button in the Bottom Right

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Select Open in OpenVPN

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Click the Green Plus Button to Import the File

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Enter the Password

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Enter the Password you created in the creation of the file, and tap the Save switch to turn it on. Finally tap the Off Switch to Connect to the VPN.

Connected!

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SECTION 9 – Install VPN Software on OSX

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Two options for a VPN application on the Mac. Donald recommended Viscosity from http://www.sparklabs.com/viscosity/download/ which is $9 per Mac.

After the show Dr. Matt suggested the free TunnelBlick from http://code.google.com/p/tunnelblick. I installed both and they both work well. This tutorial will be for Viscosity, but if you try Tunnelblick you have to do one thing to make it work. In the Settings, Configuration tab, select Advanced and then uncheck the box to use TunnelBlick’s tun/tap drivers.

Let’s keep going with Viscosity as our example.

Install Viscosity

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Click on the icon for Viscosity in the menubar and choose Preferences.

In the Connection Tab Click on the Plus Button at the Bottom

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Select Import Connection From File…

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Navigate to the File You Created for This Device

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In my case I called it alsmac so I could tell which one to open

Connection Imported

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Connect Using Menu Bar App

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Enter the Password You Created

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No clue which one of the 198 I entered, luckily I typed the same one over and over again.

Fleeting Notification of Connection

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To test mine at home I used a Mifi so I was on a different network.

Use the Menubar Icon to Disconnect When You’re Through

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If you want to prove to yourself that you’re on VPN – go to http://ipchicken.com before and after you VPN and you’ll find that your IP changes to your home IP. Congratulations!

10 thoughts on “How To Set Up a VPN Server Using a Mac”

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  4. Paolo - August 27, 2017

    Thanks for this post. I need install OpenVPN Server on my mac, but it’s very difficult find a guide that in complete. The dropbox link that you have posted is expired, can you post the Donald’s Nifty Scripts of Doom file again? thx

  5. Allison Sheridan - August 27, 2017

    Paolo – I’m sorry to say that Donald Burr has disappeared from the Internet and I’ve lost all normal methods of human communication with him. I searched my own drive to see if I’d saved a copy but I’m afraid I did not. I’m sorry to let you down like this.

  6. Cavit - April 21, 2018

    Perhaps there could be a way to replicate the missing scripts, or at least an explanation as to what to do here…

  7. Ben - September 19, 2018

    Hi all, a copy of “Donald’s Nifty Scripts of Doom” can be located here: https://www.dropbox.com/s/1em9kwbnmzp74uh/openvpn-mac.tar.bz2?dl=0

    PS. This is thanks to the wayback machine at archive.org, you should consider donating: https://archive.org
    🙂

  8. podfeet - November 29, 2018

    I just found Donald Burr again recently and he gave me a good link to the “Scripts of Doom”. Turns out they were in his Dropbox all along, but Dropbox changed the way you link to folders so it broke the connection. Enjoy!

  9. Yoyo - December 16, 2018

    Hello,

    Just have a quick question, do you know how to install the OpenVPN Access Server UI?
    Also, how many concurrent connections can you have with this?

    Thank you!

  10. Enkei - September 6, 2021

    guys this stuff no longer works…just FYI .. I got to the end to find out sysctl, ipfw and natd no longer work as expected/exist on Catalina 🙁

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