Tailscaled only working after login

macOS
1

I uninstalled the App Store version of tailscale in order to be able to remotely control a Mac which will be restarted remotely from time to time.
I would need to be able to vnc/ remote desktop into it before the login.

I am reading the official tailscaled github page and it says:

tailscaled can run at system boot before any user has logged in (e.g. letting you VNC to your computer after a power outage)

I followed the steps and I’m successfully able to load tailscale on that Mac.
However, from another computer, in the tailscale admin page if I restart that Mac I’m not seeing the little green dot and the “connected” text.
Also trying VNC/ARD it’s not reachable.
Even a simple ping, will not reach that machine.
Using CLI commands from terminal, I get correct results and everything seems running fine.
The Mac Studio is running Monterey 12.4

What could be the problem?
Anything I could try?
thanks for helping

2

are the developers looking at this forum?

3

I’ve done it before with instructions from here, where I think you found that bit. Did you try the tailscaled install-system-daemon? And did you check that it creates the relevant files in the right place?

4

They do, yes, you might try adding the SUPPORT QUESTIONS category to your post.

5

thanks.
yes, that command installed successfully the tailscaled file into /usr/local/bin
I followed all the steps in that link.

please note that all the CLI commands are working fine, and I can see the machine from the admin page, and everything works as it should, once logged in.
it’s only before logging in that it doesn’t work…

6

Is the plist file in place too? That’s what tells the Mac’s init system to start tailscaled on launch.

7

yes, the plist is there too

8

Do you have Filevault enabled on the machine? AFAIK, when Filevault is enabled, nothing will run until you have logged in.

9

Thanks, I didn’t know that – I will try first thing tomorrow.
Is it a known FileVault issue?
If so, it wouldn’t hurt mentioning that on the Tailscaled tutorial and notes!

10

After a quick test, it seems disabling FileVault solves the issue.
So I guess there’s nothing to be done on the Tailscale side? I would rather have FileVault on and using tailscaled at login.

11

FileVault is disk encryption, so when you boot up nothing useful can run because the disk is locked. It’s a security trade-off. Personally I’d rather have my disk encrypted and forego this issue than leave it unencrypted.

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