"Tailscale is not online" problem

yobyot

I'm late to the party but unless I misunderstand this thread it's not about Tailscale not starting up but instead about the auth key expiring.

Auth keys are good for a maximum of 90 days. If you reboot pfSense on day 91, Tailscale will not come up and the "API" error will be generated (it's actually an auth key expired error).

Thus, unless you never reboot pfSense, starting with the 91st day, you must re-generate an auth key and input it to Tailscale even if you have key expiry disabled.

What makes this worse, IMHO, is that the longer you go between reboots, the more obscure the problem. So, Tailscale is not a reliable service because it cannot survive a reboot after 90 days.

This occurs on both CE 2.7.2 in a Protectli Vault Proxmox VM and on a real SG-1100 running Plus 24.11 (packages as distributed with those releases).

chudak

@yobyot said in "Tailscale is not online" problem:

I'm late to the party but unless I misunderstand this thread it's not about Tailscale not starting up but instead about the auth key expiring.

Auth keys are good for a maximum of 90 days. If you reboot pfSense on day 91, Tailscale will not come up and the "API" error will be generated (it's actually an auth key expired error).

Thus, unless you never reboot pfSense, starting with the 91st day, you must re-generate an auth key and input it to Tailscale even if you have key expiry disabled.

What makes this worse, IMHO, is that the longer you go between reboots, the more obscure the problem. So, Tailscale is not a reliable service because it cannot survive a reboot after 90 days.

This occurs on both CE 2.7.2 in a Protectli Vault Proxmox VM and on a real SG-1100 running Plus 24.11 (packages as distributed with those releases).

I wish TS would introduce a new feature "a la Acme update" so that this would be done automatically.

Jim Coogan

@yobyot I think maybe it is node key expiring at 180 days?

fwiw I have discovered that running in shell

tailscale down
tailscale up --force-reauth

will give you a URL you can then paste in browser and it re authenticates and gets pfsense back online as the same machine and status shows this in pf tailscale UI. This is reauthing the node key.

The node key shouldn't expire when you set it not to on the tailscale admin but I just caught is note on https://tailscale.com/kb/1028/key-expiry
"A change to the Key Expiry value applies to any devices that are logged in after you make the change. The key expiration for any devices that are already logged in remains unchanged, until the next time the device is logged in."

So maybe when we setup pf tailscale and the subsequently disable node key expiring it doesn't take effect until reauth which maybe doesnt happen until --force-reauth and doesn't become apparant until after 180 days?

However, what I don't understand and undermines my theory somewhat is that after doing reauth, at first I noticed that restarting tailscale in pf UI caused me to be logged out again with error "You are logged out. The last login error was: invalid key: API key does not exist"

I manually updated tailscale to 1.84.2 (see https://forum.netgate.com/topic/174525/how-to-update-to-the-latest-tailscale-version/155 but basically run pkg add -f https://pkg.freebsd.org/FreeBSD:15:amd64/latest/All/tailscale-1.84.2.pkg) and then did tailscale down and up --force-reauth and this time it made me resign (I have tailnet lock on) after auth it. Now restarting the service in UI works.

Not sure yet what is going on and what role the new tailscale pkg played. One thing I suspect that maybe also is a factor is the fact that /usr/local/pkg/tailscale/state/tailscaled.state is the state file with node key instead of the standard /var/db/tailscale/tailscaled.state could be a factor On pf tailscale, /usr/local/etc/rc.d/tailscaled uses /var/db/tailscale/tailscaled.state as state directory so maybe sometimes somehow tailscale is looking for state there and it doesn't exist.

But this wouldn't really explain why everything is fine for a while initially (usually 90 to 180 days Im not exactly sure in my case). This may explain why it logs out on reboot if you if you use ram disk though.

yobyot

@chudak Yup. That's exactly what we need for this to be reliable.

AlphaDog45

I am also effected by this and it happened upon a reboot within the 180 day key expiry. Running the tailscale down and up with reuath, followed by pasting the URL into a browser fixes it, but is far from ideal.

manupfdude

Hi all,

I wanted to share that I’m also experiencing issues with Tailscale (v1.86.4) on the latest pfSense CE (v2.8.0).
After either a pfSense reboot or a Tailscale service restart, my node is logged out of Tailscale — exactly as many of you have described here.

It bothered me enough that I opened a support ticket with the Tailscale team. I explained the problem, included details, and linked this thread as a reference. The good news is that support responded quickly and said they’re setting up a pfSense VM to reproduce the issue.

In the meantime, they suggested a workaround:

“Based on the behavior described here and in the thread, it looks like the auth key used for authentication may be expiring. Since OAuth clients don’t expire, switching to an OAuth Client rather than an Auth Key might resolve this.
See our docs here:
https://tailscale.com/kb/1215/oauth-clients#registering-new-nodes-using-oauth-credentials

I tested this, and after configuring Tailscale with OAuth, everything worked!
Tailscale now stays connected and authenticated even after a reboot or service restart.

That said, I did tell support that while OAuth solves the issue, it used to work out of the box with the simpler interactive login / auth key flow. Something seems to have changed on the Tailscale side, and I hope they identify and fix it. But until then, the OAuth workaround is a solid fix.

I’d love to hear how it’s working for the rest of you.
Anyone else try OAuth yet?

Cheers

yobyot

@manupfdude This is a very inventive approach!

I'd like to try it but have a couple of questions about pfSense implementation.

Where did you enter the key and secret? And what scopes did you grant the Tailscale OAuth client?

manupfdude

@yobyot
I've SSHed into pfsense
and for the sake of testing I've simply run the command:

tailscale up --auth-key=tskey-client-kQ_THE_REST_IS_A_SECRET\?preauthorized=true\&ephemeral=false --accept-dns=false --accept-routes --advertise-exit-node --advertise-routes=X.X.X.X/24 --advertise-tags=tag:pfsense

Note the preauthorized=true and ephemeral=false
I gave this key all permissions (temporarly as I just wanted to verify it's working)
of course I had to register the tag used also in the ACL tags pane:
https://login.tailscale.com/admin/acls/visual/tags

so far so good

lbm_

@manupfdude Interesting. Thanks for the detailed answer. Im also facing the same issue unfortunately where I need to auth again after an reboot.

Are you with this approach having issues with the advertised routes not working ? I have to manually do (I havent tried your approach yet to see if this fixes the issue).

 tailscale set --advertise-routes=192.168.1/24,192.168.2.0/24 after I login. Even though they are set in the UI

yobyot

Well,

I spent some time tonight playing around with this and I think I have it.

Some suggestions for others:

Generate the OAuth client in the Tailscale admin before anything else.
Make sure to create the tag you'll need. One per pfSense instance (and clearly, one OAuth client per pfSense instance).
Give the OAuth client the permissions you think appropriate.
Very Important: make sure that you can generate an API key with the OAuth creds. The OAuth creds are, apparently, used by the CLI to generate an API key. The latter is what does the trick in tailscale up.
Do this from the pfSense console:
curl -d "client_id=kY5Mv4h8kQ11CNTRL" -d "client_secret=tskey-client-kY5[invalidchars]CNTRL-ZXo2FfBbb[moreinvalidchars]GVT" "https://api.tailscale.com/api/v2/oauth/token"
If you don't get back something like this, you'll never be able to get it to work:
{"access_token":"tskey-api-kM[lotsofinvalidchars]NTRL-[stillmoreinvalidchars]9YevL","token_type":"Bearer","expires_in":3600,"scope":"all"}
Here's what worked for me if the above returned an API token:
/usr/local/bin/tailscale up --auth-key=tskey-client-[greekedout]GVT\?ephemeral=false\&preauthorized=true --accept-dns=false --accept-routes --advertise-exit-node --advertise-routes=192.168.211.0/24 --advertise-tags=tag:[yourtaghere]
Make sure you have the cron package installed. Then add a @reboot entry using the full path (see above). I also added a cron entry every six hours as if Tailscale is up, this command does not interrupt or reset any sessions.

I've left some bytes of the creds in these examples to make it clearer where your full creds should go. The curl command requires the escape symbol (\) in the parameters that will be passed to the control plane.

FWIW, I lost an hour or more because I had (God only knows why) set Tailscale on one pfSense instance to accept DNS. Do this and the router cannot resolve the control plane API endpoint. Dumb. And I own it.

I don't know if this "fixes" everything. But it's a lot of work and it shouldn't be necessary. Somehow, this package to be useful needs to survive reboot without the need to go to these lengths.