System software has been updated - reboot loop

[Sandor Patocs]

I actually only need Tunnelblick to provide /dev/tap? devices.  I don't use it for connecting to a VPN.  I use the tap devices with Qemu, to provide advanced networking that is unavailable by any other means.

I somehow managed to get it working on my work laptop, but now I'm trying to do the same on a second laptop and am stuck in an endless loop.

I have tried this on:

MacOS 12.4

MacOS 12.6.1

MacOS 13.0.1

I get the same behavior with every operating system I've tried.

I followed the instructions provided here:  https://tunnelblick.net/cInstall.html and https://tunnelblick.net/cKextsInstallation.html

I have enabled the use of kernel extensions via the Startup Security Utility.

The problem is that every time I reboot, in System Preferences I see this message:

System software from developer "Jonathan Bullard" has been updated.

I click "Allow", reboot and then get the following message:

An error occurred with your system extensions during startup and they need to be rebuilt before they can be used. Please go to Security and Privacy System Preferences to re-enable them.

And with that, I'm right back to where I started ... System software from developer "Jonathan Bullard" has been updated.

If I attempt to run "/Applications/Tunnelblick.app/Contents/Resources/openvpnstart loadKexts 2" I get the following error:

Tunnelblick: runTunnelblickd: no data available from tunnelblickd socket; sleeping 5.0000 seconds ...

Failed to load the tap kext; status = -603946981

Any help would be appreciated.

[Tunnelblick developer]

The message "Tunnelblick: runTunnelblickd: no data available from tunnelblickd socket; sleeping 5.0000 seconds ..." means that Tunnelblick's "daemon" (used to perform privileged tasks) is not responding in a timely way. It may just be slow, or it may not be running at all. "openvpnstart" uses the daemon, so if it isn't running, the "openvpnstart" will fail.

I think the daemon is exercised by Tunnelblick's startup process, so if you can launch Tunnelblick, it's icon appears in the menu bar, and you can click on that and get the "VPN Details" page, the daemon is probably OK. But if you can't, there is something interfering with the daemon. I don't know what, though.

[Sandor Patocs]

I'm able to run the Tunnelblick app and get to the VPN Details window.  I've also tried installing the extension from the Utilities tab in that window.  That did not help either.  It appears that just copies files to /Library/Extensions.

Is there a way to launch the daemon manually, possibly with logging set to "debug"?

The root of the problem seems to be whatever is causing the OS to think the kext has been updated after every reboot.  Any idea what might be getting updated to trigger this?

[Tunnelblick developer]

The daemon and the kexts are two completely separate and distinct things, but if there are problems with the daemon the kexts won't load, because it is the daemon that loads them.

The daemon can't be launched manually; it is launched by sending a message to a socket. "openvpnstart" sends such messages to perform privileged functions such as loading kexts.

However, the log for the daemon can be found in Console and it might help to look at it. It is in "Log Reports" section and is named "tunnelblickd.log". It will usually only contain entries noting the creation and deletion of temporary directors and cleanup when a reboot is detected. It will also contain "Timed out; exiting" entries which are entirely normal: after the daemon is started and processed the stream of instructions available to its socket, it waits around for a while to process new instructions and if it doesn't get any for a while it exits.

[Sandor Patocs]

My problem actually occurs before I attempt to run "openvpnstart".  The problem is that after I approve the system extension in System Preferences I am asked to reboot.  I reboot and as soon as I log in, I get the following error message:

An error occurred with your system extensions during startup and they need to be rebuilt before they can be used. Please go to Security and Privacy System Preferences to re-enable them.

I don't understand what that message is trying to tell me, but clicking "Allow" again in System Preferences and rebooting again results in the exact same error message being displayed.  It's an endless loop.

I only attempted to run "openvpnstart" on the off chance that it could provide additional details/error messages, which it did not.

I've also looked at the tunnelblickd.log output in Console and the output looks exactly the same after every reboot. The daemon is doing what appears to be routine housekeeping and then timing out before exiting.

But again, the problem appears to be external to the Tunnelblick application itself.  The problem appears to happen during the boot up process.  The "system" wants me to approve the system extension after every reboot.  My approval never sticks because of some sort of error during startup.  I don't know how to troubleshoot, identify or remedy the startup error.  The interaction, during boot, between the system and the Tunnelblick system extensions seems to be the problem.

And, thank you to everyone who has responded thus far.