Through The Looking Glass Mac OS

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

If you have an M1 Mac, also see Tunnelblick and Apple Silicon.

If you are using macOS Big Sur, you should use the latest beta version of Tunnelblick. You should allow Tunnelblick to automatically check for updates on the 'Preferences' panel of Tunnelblick's 'VPN Details' window. Be sure to put a check in 'Check for updates to beta versions'.

The following is the current status of issues that have been seen using Tunnelblick on macOS Big Sur.

To report an issue, please follow the instructions at Tunnelblick Issues.

FIXED in Tunnelblick 3.8.5beta03: Tunnelblick's Tun and Tap system extensions do not load.

If your configuration requires a Tun or Tap system extension, connecting to your VPN will fail if an appropriate system extension is not installed.

  • If you are using a Tun VPN, you can — and should — modify your OpenVPN configuration file so it will work without the 'Tun' system extension. See Errors Loading System Extensions for instructions.
  • If you are using a Tap VPN, your configuration requires a Tap system extension.

A future version of macOS will not allow the use of Tunnelblick's system extensions. See The Future of Tun and Tap VPNs on macOS.

See Installing System Extensions for detailed instructions on installing Tunnelblick's system extensions.

FIXED in Tunnelblick 3.8.5beta03: Tunnelblick disables loading of Tun and Tap system extensions.

When running on macOS Big Sur 11.0.1 or later, some versions of Tunnelblick force the settings on Tunnelblick's 'Advanced' settings window to 'never load' system extensions.

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

(This issue is not specific to Big Sur. It is present in all versions of Sidecar.)

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'.
  • Through the Looking Glass This all sounds like I’ve just been waiting to unload on Windows, but that’s not the case. Most of the time, my laptop works great.
  • Alice suddenly finds herself on the mantelpiece and steps through the mirror into Looking-Glass House. On the other side of the mirror, Alice discovers a room similar to her own but with several strange differences. The chessmen stand in the fireplace in pairs, oblivious to Alice’s presence. She comes to the aid of the White Queen’s.

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For the final release, the game's name was changed from 'Alice' to 'Through the Looking Glass' due to legal reasons. The name 'Alice' was already in use for a database program. In 1984, these graphics must have blown people away! I guess the whole idea behind this game was to show people the power of the Macintosh’s graphics capabilities.