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The following is the current status of issues that have been seen using the latest stable version of Tunnelblick on the latest version of macOS Catalina.

Important: See The Future of Tun and Tap VPNs on macOS for information about changes to future versions of macOS.

NEW macOS REQUIREMENT: Restarting the computer is required by macOS Catalina before connecting some configurations for the first time.

If a configuration requires a 'tun' or 'tap' system extension, the first time Tunnelblick asks macOS to load the appropriate system extension, macOS will tell the user that they must give permission to load system extensions signed by 'Jonathan Bullard' in System Preferences : Security & Privacy : General. If the user gives such permission by clicking 'Allow', macOS must restart the computer before the permission will be honored. After the permission has been given and the computer has been restarted, you may then connect all VPN configurations normally.

This only needs to be done one time. Once permission to load system extensions signed by 'Jonathan Bullard' has been granted and the computer has been restarted, no further action is needed. Tunnelblick will be able to load 'tun' and 'tap' system extensions for any configuration without user interaction, and that ability will persist after computer restarts, 'safe boots', and updates to Tunnelblick.

Note: If you are using a 'tun' VPN, you can avoid needing to load the 'tun' system extension. See the note at the start of Errors Loading Kexts (Device Drivers).

WON'T FIX: Sidecar does not work when a VPN is connected using Tunnelblick's default for a configuration.

Sidecar does not work if IPv6 is disabled. By default, Tunnelblick disables IPv6 while a VPN is connected. This is done to prevent information leaks in common VPN setups (see A Glance through the VPN Looking Glass: IPv6 Leakage and DNS Hijacking in Commercial VPN clients).

To fix this problem:

  1. Verify with your VPN service provider that no information is leaked if IPv6 traffic is allowed. If you cannot confirm that, you should not proceed and you will not be able to use Sidecar when your VPN is connected.
  2. Launch Tunnelblick.
  3. Click the Tunnelblick icon in the menu bar and then click 'VPN Details'.
  4. Click on the large 'Configurations' button at the top of the window.
  5. Select the configuration(s) you wish to modify.
  6. Remove the check from 'Disable IPv6 unless the server is accessed via IPv6'.

(This page was updated 2020-07-12.)

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Installing OpenVPN on macOS X

Tunnelblick is free, being an open-source OpenVPN software created for Mac OS X. You can download the latest software from the Tunnelblick website in the downloads section. Execute the downloaded .dmg file and follow the instructions to install it.

Oct 04, 2019.

At the end of the installation process, Tunnelblick will ask if you have any configuration files. If you haven’t used it before, select No and let Tunnelblick finish the initial process. Open a search window and execute the client.ovpn file, and Tunnelblick will install the client profile. Administrative rights are required.

How to connect to an OpenVPN server on macOS X

Launch Tunnelblick by opening Tunnelblick in the Applications folder. Once Tunnelblick is launched, an icon will appear in the menu bar in the upper right to control the connections. Click on the icon and then on the Connect menu to start the VPN connection. Select the correct client connection affiliated with the certificate imported earlier.

Installing OpenVPN on iOS

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From the iTunes App Store, look for and install Open VPN Connect, the official iOS Open VPN client application. To transfer the iOS client configuration (or certificate) to the device, connect it directly to a computer.

The finalization of the transfer will be done using iTunes. Open iTunes on your computer and click iPhone> apps. Scroll to the bottom of the File Sharing section and click on the OpenVPN application. On the opened empty page on the right, navigate to the OpenVPN documents, which is for file sharing. Drag the .ovpn file into the OpenVPN Documents window.

Now launch OpenVPN on iPhone. There will be a notification that a new profile is ready to import. Touch the green plus sign to import it.

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How to connect to an OpenVPN server on iOS

OpenVPN is now ready for use with the new profile. Start the connection by sliding the Connect button to the On position. Disconnect by sliding the knob to the Off position.

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Note: The VPN switch under Settings cannot be used to connect to the VPN network. If you try, you will receive a notification to connect only using the OpenVPN application.