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I am a macOS user, and joined the Big Sur public beta. I frequently use TunnelBlick for accessing my office's VPN to work from home or assist off-hours, however, the Big Sur betas have disabled the loading of system extensions that enable TunnelBlick to link to a TUN VPN (link here).

I was wondering if it is possible to use a Docker container running an OpenVPN client, and tell my macOS host to use the container as a gateway so that the traffic goes through the VPN. If not possible as a system-wide gateway, is it possible to configure Microsoft's Remote Desktop connection gateway to that container?

Thank you for your help, Regards.

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Before you try Docker for this...

I had the same issue after upgrade to Big Sur. Vpn to my nighthawk stopped working.

(https://tunnelblick.net/cKextLoadError.html) TAP mode is not supported anymore, but TUN should work. And you should check if your VPN server also supports TUN. My router (Netgear nighthawk) had support for TUN on a different port.

Solution using tunnelblick (or Viscosity):
Download settings "for non-windows" from Netgear advance seutp->VPN Service
Edit the. xxxx. conf file change the line starting with "remote" to "TUN"
port (ip and port available in in Netgear advance seutp->VPN Service->tun mode service port)
Change "dev tap" to "dev tun"
Save
Add .tblk to the downloaded folder.
Drag to Tunnelblick (or import to Viscosity VPN)
Connect from Big Sur should now work.

More details here: https://tunnelblick.net/cTunTapConnections.html

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  • Thank you @Kb., however I am not able to change the server to TUN connections as it is my company's VPN server, which I do not control. It is, however, a nice to know workaround if the change is feasible.
    – Alexandre Vieira
    Commented Nov 19, 2020 at 23:07
  • The change to TUN would be at the client, most VPN servers serves both TUN and TAP. Most likely your company's VPN also serves TUN. For the client you just need to get the servers TUN port, and then it should work.
    – Kb.
    Commented Nov 20, 2020 at 21:02

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