How to update to the latest Tailscale version?
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CAUTION
I had the following error message after upgrading and restarting the daemon. This time I simply typed "tailscale login" and pasted the authentication URL into a browser to re-authenticate. I did not need to generate a new key.
# Health check: # - You are logged out. The last login error was: invalid key: API key does not existUpdated CE 2.8.1 to 1.96.4
pkg add -f https://pkg.freebsd.org/FreeBSD:15:amd64/latest/All/tailscale-1.96.4.pkg -
Upgraded pfSense to version 26.03 - Tailscale Package version 0.1.9_2 - Package Dependencies: tailscale-1.94.1. Afterward, I only had to restart Tailscale and re-advertise routes. The Tailscale version remained the same as before the pfSense upgrade, 1.94.1_2.
Updated to 1.96.4; no errors.
After the updates, I always have to restart Tailscale and re-advertise routes. -
@elvisimprsntr I had to re-authenticate after the last update (to version 1.94.1_2) and every time the service restarted while on that update but I stopped the tailscale service and logged out of it as described by @CarlMRoss above (service tailscaled stop && tailscale logout) before this update and I didn't have to log back in manually after the update to 1.96.4.
I think the theory up-thread that one of the updates may have corrupted the saved login credentials when done on a running tailscale service may be correct. I'll just keep this extra step as part of the procedure since it seems to have fixed the issue for me.
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I stopped using the logout command in the last update; as far as I could tell, it does nothing after 'service tailscaled stop'.
At the end of last year, I decided to do a clean restart and, afterward, apply all Tailscale updates and settings changes via SSH. I uninstalled the tailscale package, then deleted all leftover tailscale files and settings. After that, I reinstalled the package and then updated Tailscale via SSH from Freshports. Since then, no errors, no need to generate new keys or re-authenticate.
I always need to re-advertise routes after every update and after the rare pfSense reboot. I have searched for a solution, but none of the suggestions have seemed worth pursuing.
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tailscale logout is not required to prevent the corruption event. The only thing that is absolutely required is to manually stop the tailscale service, whether by disabling Tailscale in the VPN menu of the Web Configurator or by command-line as @CarlMRoss alluded to. I just tested this myself as my pfSense box was still running 1.94.1 and had no issues.
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New Tailscale pricing. Positive changes overall
https://tailscale.com/blog/pricing-v4
+Unlimited devices, up to 6 users
-3 ACL groups, 50 tagged resources
?1000 (Temporary) ephemeral resources
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No login or authentication issues this time.
Updated CE 2.8.1 to 1.96.4_1
pkg add -f https://pkg.freebsd.org/FreeBSD:15:amd64/quarterly/All/tailscale-1.96.4_1.pkg -
@elvisimprsntr said in How to update to the latest Tailscale version?:
No login or authentication issues this time.
Wasn't the case for me. Even though I stopped the Tailscale service before updating, I still had to reauthenticate using the existing key. Thankfully it didn't take much time to fix thanks to the discussion here.
It's weird that it's so unpredictable though.
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Updated to version 1.96.4_1, no issues, no errors.
System: pfSense+ 26.03, Tailscale Package 0.1.9_2, Package Dependencies: tailscale-1.94.1, Freshports-tailscaled version 1.96.4_1
I’ve seen unpredictable behavior since I started doing FreshPorts updates on pfSense+ 24.x. What has worked better for me is stopping the service before the update and restarting it afterward. After reboots, I’ve sometimes had to run some version of service tailscaled stop, service tailscaled start, and tailscale up to get things stable again.
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said in How to update to the latest Tailscale version?:
Updated to version 1.96.4_1, no issues, no errors.
Updated to version 1.96.4_2
service tailscaled stopfetch https://pkg.freebsd.org/FreeBSD:16:amd64/latest/All/tailscale-1.96.4_2.pkg || exit 1 && pkg-static add -f tailscale-1.96.4_2.pkg && rm -f tailscale-1.96.4_2.pkg && service tailscaled startAfter upgrading pfSense+ to 26.03, I added advertised routes in the Tailscale web GUI, and there have been no issues with Tailscale updates or pfSense reboots since then.
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Updated CE 2.8.1 to 1.98.2
pkg add -f https://pkg.freebsd.org/FreeBSD:15:amd64/quarterly/All/tailscale-1.98.2.pkg -
Updated CE 2.8.1 to 1.98.3
pkg add -f https://pkg.freebsd.org/FreeBSD:15:amd64/latest/All/tailscale-1.98.3.pkg -
Updated CE 2.8.1 to 1.98.4
pkg add -f https://pkg.freebsd.org/FreeBSD:15:amd64/latest/All/tailscale-1.98.4.pkg -
Updated CE 2.8.1 to 1.98.5_1
pkg add -f https://pkg.freebsd.org/FreeBSD:15:amd64/latest/All/tailscale-1.98.5_1.pkg
