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OpenVPN for Apple MacOS (with Tunnelblick)

If you would like to set up a connection to proxy.sh OpenVPN tunnels on Mac OS X, you need to install an additional piece of software. In this tutorial, we will use the freeware called Tunnelblick.

Start by downloading Tunnelblick for your version of Mac OS X.

        Mac OS X Lion and earlier: Tunnelblick stable release
        Mac OS X Mountain Lion: Tunnelblick beta release

If not done automatically, open the disk image and drag the Tunnelblick icon to your Applications folder. Do not start Tunnelblick right out of the disk image.

Download *.ovpn from the link given in your welcome email or via your active VPN package product details (or you can use our configuration files generator), to your Downloads folder. Same for the proxysh.crt file.

Now open Tunnelblick from the Applications folder by clicking on its icon.

While installing Tunnelblick, you need to enter your admin user's credentials from time to time. The first time the admin credentials are needed to change the ownership and permissions of the Tunnelblick executables. Enter your admin credentials and click OK.

First run configuration dialogs are displayed. Click I have configuration files.

Click OpenVPN configuration(s) to use the previously downloaded configuration file (*.ovpn).

You need to copy *.ovpn file along with the proxysh.crt one to the configuration file folder of Tunnelblick. This folder is hidden on a regular Mac OS X installation. To open it, click Open Private Configurations Folder.

A message is shown informing you, that the Private Configuration Folder is Open. Keep this message open and continue with the next step.

A Finder window should have popped up. Copy the downloaded configuration file *.ovpn from your Downloads folder into here. Do the same with the .crt file.

Now get back to the Private Configuration Folder is Open message and click Done.

You will be asked to check for updates automatically. Uncheck Include anonymous system profile, then click Check Automatically.

You need to enter your admin credentials once more. This time for changing the ownership/permissions of the configuration file. Enter your admin credentials and click OK.

Tunnelblick has placed an icon in the menu bar. Click on it and select Connect PROXY.SH.

Enter your proxy.sh VPN credentials in the Username and Password fields. For convenience, check Save in Keychain. Click OK.

Three black translucent status windows appear, one after the other, displaying the connection state.

After having successfully connected, the Tunnelblick icon in the menu bar changes to an illuminated one and the status window disappears.

That's it. Enjoy!

NB: If you encounter difficulties to connect with OpenVPN, please try to connect to other servers or try alternative ports, especially more "discreet" ones such as TCP 443 or TCP 80. Please also make sure that the port you are connecting through is fully opened in your firewall/router/network. Below, you will find an aggregate of useful guides and articles that will help you troubleshoot your problems, should you have any.

Guide for setting up Safejumper (OpenVPN) on Apple MacOS.
I cannot find the .ovpn and .crt files necessary for OpenVPN. Where are they?
No matter how hard I try, I cannot succesfully connect to OpenVPN.
I can't access any website through my browser while connected to VPN.
I am connected to the VPN but my IP is not yet hidden. Help!
I am having some kind of other problem. Where can I find some help?
How can I find the local log files of my VPN client?

If you still cannot connect successfully, please open a support ticket and include either a copy of your logs or a screenshot of your configuration and encountered errors. Logs can usually be found in software menus or settings, as well as their directories of installation (.log or .txt files). If you do not include a log or a screenshot, it will be hard for us to help you resolve the issues you have with connecting to our network.
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