Connecting to a File Server via OpenVPN on Mac OS X 10.5

This topic assumes you already have Open VPN set up on your system. If you need help with that, please see this tip.

How to connect to your company file server when you are not on the compan LAN, but otherwise have high speed access (Starbucks, hotel/home connection, high speed wireless, etc.).

Launch the Viscosity application

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Viscosity is the application used to create the VPN "tunnel" or connection. It may already be running on your system; if so you’ll see a small icon in the upper left of your Menu bar that looks like an unlocked lock. If not, find and double click on the Viscosity application inside your Applications folder. The window above shows you how to access your Applications folder. Note – the application automatically updates itself, so ocasionally you may see a request to install the update. It’s OK to allow this to happen.

Viscosity Menu Item

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If you look closely, the only thing that changed when you launched Viscosity was the addition of this item in the menu bar at the top left of the screen. Look closely!

Viscosity Menu Item … again

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When you click on the Viscosity menu, a list of available VPN settings. You probably only have one connection, but you can certainly have as many VPN connections as you need. To initiate a connection, just release the mouse on Connect…

Successful connection

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If the connection was successful, you’ll get a green Viscosity icon. At this time, you are connected to your remote network.

Connecting to remote file servers

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Once you have made the connection, head back to the Go menu in the Finder and choose Connect to Server…

Connect to Server

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The main difference between connecting to a server via a VPN and a local connection is that VPN connections don’t pass the Bonjour names of servers or show up at all – so you have to know the IP address or name of your intended connection. Enter the IP address of the server you want to connect to, and press Connect. If you don’t want to have to remember your server’s IP address, you can drag the Server Address Field into the Favorite Servers window. Once you’ve done this step, you’ll see the familiar dialog box to allow you to select which share point to mount.

Printed version

To download a PDF file with this tip, click here.

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Setting up OpenVPN on Mac OS X 10.4 (client section)

Setting up OpenVPN using the free Tunnelblick software. This software isn’t as easy to set up as the $9 Viscosity, but it works the same once it’s configured.

Download the VPN software

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Download the client from http://code.google.com/p/tunnelblick/

Tunnelblick_(version).dmg will download. Double click on that file to mount the disk image.

Install Tunnelblick

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Drag the Tunnelblick.app file to your Applications folder. You can do this in that window by clicking and dragging. Do not launch the application yet.

Distributing the client via email

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Follow the link in the email message you recieved, or download the attachment in the email from the VPN admnistrator.

Click here… or copy and paste into your web browser.

If you got a message from your administrator with a file called config.zip attached, skip ahead to "Download the VPN software."

Secure Connection Failed

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If you get this screen because you are using Firefox, visit https://4macs.wordpress.com/2009/01/07/firefox-3-and-invalid-security-certificates/ to learn how to get around this.

Note – you may not see this warning in other browsers, so you can ignore this step if you don’t have the problem.

Downloading the configuation file

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For Mac users, click on the Configuration Files link.

A file called "config.zip" will download, and may automatically decompress to a folder called "untangle-vpn." If it does not do this automatically, double click on the config.zip to make this happen.

Installing the configuration files

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This step may be a bit tricky, so pay attention.

In the root level of your hard drive (what you see if you click on Macintosh HD on your desktop), there is a folder called Library. Open this folder and create a folder called "openvpn." This Library folder IS NOT in your User’s Home folder – that’s where you see Desktop, Documents, Downloads, Movies, Music, Pictures, etc.

Then drag contents of the untangle-vpn folder to this folder, so it looks like this. The outlined portion is shown just to show you the location of the folders.

Very important – inside the folder called untangle-vpn IS ANOTHER folder called untangle-vpn. Confusing, I know, but I didn’t write it! Make sure you drag the contents of the first untangle-vpn folder, not the inner one. You should drag the files as shown in the picture above.

Launch Tunnelblick

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Launch the Tunnelblick application from your Applications folder. If you can’t find the Applications folder, use the Go menu in the Finder’s menu bar.

You will get a warning message the first time that looks like the next step.

Welcome to OpenVPN

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If you followed the installation steps above correctly, click Continue.

Checking for updates

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Tunnelblick checks for updates automatically, if you allow it. It’s a good idea to "Check Automatically" because it only gets better with each new release.

Tunnelblick’s icon

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The only interface for Tunnelblick is this icon, which will appear in your menubar at the top of your screen.

Click on the icon to show this menu

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The drop down box will show you a list of connections. It may not be nameed openvpn, but it may show something different. That’s ok, release them mouse button on the connection you want to make.

Authorize the connection

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The first time you connect, you’ll be asked for your computer account password. Enter it and press OK.

Successful connection

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If all goes well, you’ll see the "light at the end of the tunnel!" – not the subtle changes in the icon indicating the connection.

Connecting to remote file servers

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Once you have made the connection, head back to the Go menu and choose Connect to Server…

Connect to Server

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The main difference between connecting to a server via a VPN and a local connection is that VPN connections don’t pass the Bonjour names of servers or show up at all – so you have to know the IP address or name of your intended connection. Enter the IP address of the server you want to connect to, and press Connect.

Remote Printers

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You can also print to remote printers. In System Preferences, choose Print & Fax, then hit the + to add the printer. The thing to remember hereis that the printer must be accessible via an IP address – so USB connected printers won’t work. Note – these screenshots are from 10.5, but the printer setup is nearly identical, but don’t expect to see exactly what you see here if you are running 10.4.

Adding an IP Printer

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Choose IP from the icons on the top. Then enter the Address of the printer in that field. Most of the time you can leave Queue empty. And as long as you have the printer drivers installed on your machine, the computer will find the proper settings files. The IP address will automatically show in the Name field, but feel free to change the name of the printer to something easily identifyable.

REMEMBER: You must be connected to the VPN in order to print to a remote printer!!! IT’s probably best not to make this new printer the default printer unless you plan on being connected to the VPN all of the time.

Setting up OpenVPN on Mac OS X 10.5 (client section)

Setting up OpenVPN using the $9 Viscosity application. This software is very easy to set up and use. If $9 is more than you want to pay, consider using Tunnelblick. Viscosity doesn’t yet work fully on 10.4, but it should soon – check the website.

Distributing the client via email

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Follow the link in the email message you recieved, or download the attachment in the email from the VPN admnistrator.

Click here… or copy and paste into your web browser.

If you got a message from your administrator with a file called config.zip attached, skip ahead to "Download the VPN software."

Secure Connection Failed

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If you get this screen because you are using Firefox, visit https://4macs.wordpress.com/2009/01/07/firefox-3-and-invalid-security-certificates/ to learn how to get around this.

Note – you may not see this warning in other browsers, so you can ignore this step if you don’t have the problem.

Downloading the configuation file

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For Mac users, click on the Configuration Files link.

A file called "config.zip" will download, and may automatically decompress to a folder called "untangle-vpn." If it does not do this automatically, double click on the config.zip to make this happen.

Download the VPN software

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Download the client from http://viscosityvpn.com/

Viscosityvpn.dmg will download. Double click on that file to mount the disk image.

Viscosity.app

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Drag the Viscosity.app to your applications folder. You can just drag it right in that window, from the left to the right.

Eject the disk image and throw the Viscosity.dmg file in your trash can.

Launch the Viscosity application

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Moments ago, you copied this file to your Applications folder. The window above shows you how to access your Applications folder. Find the Viscosity application and double click on it to launch it. Note – the application automatically updates itself, so ocasionally you may see a request to install the update. It’s OK to allow this to happen.

Viscosity Menu Item

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If you look closely, the only thing that changed when you launched Viscosity was the addition of this item in the menu bar at the top of the screen. Look closely!

Viscosity Menu Item

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If you click the Viscosity icon in your menu bar, the only options are for Preferences or Quit. Choose Preferences. Then click the + in the lower left corner and choose Import connection. A standard Open Dialog box will appear. Navigate to your ungangle-vpn folder and choose the .ovpn or .conf file – it doesn’t matter which one you choose, Viscosity gets the information it needs from either one.

Successful import

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If the import was successful, you will see the name of the connection in the window, along with the Disconnected status.

Viscosity Menu Item … again

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Now when you go to the Viscosity menu, you will see the imported VPN settings. You can have as many connections as you like. To initiate a connection, just release the mouse on Connect…

Successful connection

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If the connection was successful, you’ll get a green Viscosity icon. At this time, you are connected to your remote network.

Connecting to remote file servers

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Once you have made the connection, head back to the Go menu and choose Connect to Server…

Connect to Server

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The main difference between connecting to a server via a VPN and a local connection is that VPN connections don’t pass the Bonjour names of servers or show up at all – so you have to know the IP address or name of your intended connection. Enter the IP address of the server you want to connect to, and press Connect.

Remote Printers

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You can also print to remote printers. In System Preferences, choose Print & Fax, then hit the + to add the printer. The thing to remember hereis that the printer must be accessible via an IP address – so USB connected printers won’t work.

Adding an IP Printer

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Choose IP from the icons on the top. Then enter the Address of the printer in that field. Most of the time you can leave Queue empty. And as long as you have the printer drivers installed on your machine, the computer will find the proper settings files. The IP address will automatically show in the Name field, but feel free to change the name of the printer to something easily identifyable.

REMEMBER: You must be connected to the VPN in order to print to a remote printer!!! IT’s probably best not to make this new printer the default printer unless you plan on being connected to the VPN all of the time.