Well… I am out of ideas. I made a new sys-tailscale using the template that works for my working sys-tailscale. I did everything the same way as the working one, and triple checked it. And the login is not persisting across reboots. So crazy, I thought for sure it would work when I used the working template.
Check the content of the files configured in your working sys-tailscale bind-dirs. Specifically the /etc/default/tailscaled. Try to copy /etc/default/tailscaled from your old sys-tailscale to the new sys-tailscale. Maybe there is some non-default configuration in these files that is not in the newly created sys-tailscale.
Sorry about the delay, work was very busy the rest of the week.
I just checked the directories you mentioned and tried copying. I found that /var/lib/tailscale has a file and a directory that persist in my working sys-tailscale, but not in my non-working one. The directory is bound in both, and I copied the bind-dirs conf directly over. A file named derpmap.cached.json does not persist. And the directory /var/lib/tailscale/files does not persist, even though /var/lib/tailscale is bound. In the files directory it has my authentication it looks like. The only file is named for my username with the service I use to authenticate tailscale with. I added that directory to bind.dirs even though it is a sub directory of a /var/lib/tailscale that is already bound just to see if that would do it, but the file and directory are missing on reboot.
At this point I am about 99.99% certain that the issue is that /var/lib/tailscale is not persisting even though it is bound in /rw/config/qubes-bind-dirs.d/50_user.conf
Any idea why that might be or what I could do to remedy it?
Do you have the /var/lib/tailscale directory in bind-dirs?
ls /rw/bind-dirs/var/lib/tailscale
No, I have it in my /rw/conf/qubes-bind-dirs.d/50_user.conf file. I did not realize that was an option to have it that way. To I just create that directory? Or copy the existing directory over to that path?
I am checking now if it is like that in my working sys-tailscale
Well, evidently I knew I was supposed to do that at some point because it is under there in my working sys-tailscale. Or is that done by the conf file?
You need to create this directory manually for bind-dirs to work:
sudo mkdir -p /rw/bind-dirs/var/lib/tailscale
It’s described in docs:
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OK, I did that, and I rebooted, and it persisted. /rw/bind-dirs/tailscale is still there, and the sub directories within it are there, all of it is there as it should be. But tailscale login did not persist. Checking /var/lib/tailscale it is missing the derpmap file and the files directory
I just ran diff on one of the files that persisted with the one under /rw/bind-dirs and they have different content
Did you create /rw/bind-dirs/tailscale or /rw/bind-dirs/var/lib/tailscale?
Try to login again and see if it’ll create files in /rw/bind-dirs/var/lib/tailscale that will persist after reboot.
/rw/bind-dirs/var/lib/tailscale
I am going to start fresh on a new sys-tailscale to make sure I don’t have any mistakes left over messing me up. Hopefully this will do it
Good news! I have a working new sys-tailsale. Thank you for all the hlep, I guess I forgot a whole lot of steps since the last time I did this. That being said, this guide is totally wrong: Tailscale
Should I update it with the right way to do this?
Yes, it’d be nice if you did it.
What is the proper way to do that within the community guidelines?
yes, I have that button
Then you can just edit it directly.
OK cool, thank you again for walking me through this. I appreciate the time you took to help me out