OpenVPN for Mac OSX

This guide explains how to set up OpenVPN on Mac OS X using Tunnelblick, the official free OpenVPN client for macOS. These instructions apply to Network Box VPN configuration files provided to you.

1. Download and install an OpenVPN client for macOS (example: Tunnelblick).
   • Download the disk image (.dmg) from: https://tunnelblick.net/downloads.html
   • Open the downloaded disk image (it will mount).
   • Double-click the Tunnelblick icon and follow the installation prompts.
2. Create a new folder (your Desktop works well).
3. Copy the configuration files that were emailed to you into that folder:
   • If authenticating via Active Directory, you need only:
     • ca.crt
     • roaming.ovpn
   • If authenticating via private certificates, you need:
     • ca.crt
     • yourname.ovpn
     • yourname.crt
     • yourname.key
   • Note about file extensions: Sometimes .crt files are emailed as .trc to bypass Microsoft Outlook attachment restrictions. Rename them back to .crt (e.g., ca.trc → ca.crt).
4. Add .tblk to the end of the folder name.
   • Example: rename MyVPN to MyVPN.tblk. The folder icon should change into a Tunnelblick VPN configuration.
5. Install the configuration
   • Double-click the folder’s new Tunnelblick icon to install it.
   • You will be asked whether the configuration should be:
     • Private — only usable when you are logged into the computer.
     • Shared — usable by any user account on the computer.
6. After installation
   • Tunnelblick will copy the .tblk to a special location on your computer and modify it so it can be used securely.
   • You can delete the original .tblk you created, or move it somewhere convenient as a backup.
   • The configuration(s) will be available immediately in Tunnelblick.

Note: The first time Tunnelblick is run on a given Mac, it will ask for the system administrator’s username and password. This is required because Tunnelblick needs root privileges to modify network settings when connecting to the VPN.

Troubleshooting OpenVPN on Mac OS X

• If the configuration does not connect, verify that your .crt files were renamed correctly.
• If prompted repeatedly for credentials, confirm whether your setup uses Active Directory or certificate authentication.
• If Tunnelblick reports permission errors, ensure you entered an administrator username and password when prompted.