Using OpenVPN on Mac admin 2017-09-22T18:16:16+00:00 Connecting to the OpenVPN from Mac MCECS provides OpenVPN as the prefered VPN solution for accessing protected MCECS resources (such as printers, and computers that support Remote Desktop or VNC.
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 PreferencesSelect AdvancedCopy the Mac AddressOpen AirPort Utility
Click on your router, in my case it’s called White Dart.
Select Enter Router Password
Enter your password when prompted and click OK.
Select EditSelect the Network Tab and Click the + ButtonPaste in the Mac Address You Copied EarlierSelect UpdateSelect Continue
Quit Airport Utility when this operation completes.
SECTION 2 – Creating Account at No-IP.com
Navigate to http://www.noip.com and select Sign Up.
Create a Username and Password
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 UpEmail Confirmation Will be SentClick the Link in the EmailDownload the Update Client
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 ClientEnter Your No-iP.com Account Info You Just Created
This menu should pop up automatically.
Click OKClick on Hosts and Check the Box Next to the Host Name You Chose
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 NowTurn on the Daemon
I chose this rather than running the application in the background all the time.
Openvpn Mac FreeSECTION 3 – Installing Xcode and Running Command Line ToolsInstall XcodeInstall Java
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
Wait till the installation finishes and quit X-Code
Type xcodebuild -license to Open the License AgreementStart Hitting the Space Bar to Scroll Through the EULA – A LOT of TimesType Agree
Type agree
Joy of AgreementSECTION 4 – Installing MacPorts
Navigate to https://distfiles.macports.org/MacPorts/ and scroll to the bottom to download the installer file for your OS.
Install MacPortsEnter These Commands in the TerminalOpenvpn For Mac Os X DownloadTo run the self update to Macports enter:
and enter your administrator password
SuccessOpen the VPN SoftwareEnter
and watch a lot of glop go by…
SECTION 5 – Installing Tuntap Drivers
Download tuntap drivers from http://tuntaposx.sourceforge.net/download.xhtml
Open the Package File (in the folder after tuntap expands)
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 ScriptsOpenvpn For Mac Os X DownloadSetting Up OpenVPN ServerWe’re now going to run Donald’s scripts. Enter this command:
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
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 KeyAnd Again for Some ReasonKeep Answering…And AgainAnd Again…Whew!
Enter passphrase and password as many times as they ask for it!
Finder Window Opens Showing config-files
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 HaveIn Terminal, enter:
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.
Text Tool: Draw the text along the path and change the text setting including bolding, italics and kerning.
![]() SECTION 7 – Opening up UDP Port 1194
Open Airport Utility again, select your Airport again, Select Edit again. Select the Network tab, and select the + under Port Settings
Enter Information As ShownSelect Update
Wait until your Airport updates.
SECTION 8 – Install VPN Software on iOS
Download OpenVPN Connect from the iTunes App Store.
Open Dropbox
Find the file you created and moved into Dropbox and tap on it.
Select the Open In Button in the Bottom RightSelect Open in OpenVPNClick the Green Plus Button to Import the FileEnter the Password
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!SECTION 9 – Install VPN Software on OSXTwo 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
Click on the icon for Viscosity in the menubar and choose Preferences.
In the Connection Tab Click on the Plus Button at the BottomSelect Import Connection From File…Navigate to the File You Created for This Device
In my case I called it alsmac so I could tell which one to open
Connection ImportedConnect Using Menu Bar AppEnter the Password You Created
No clue which one of the 198 I entered, luckily I typed the same one over and over again.
Fleeting Notification of Connection
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
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!
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