How to update to the latest Tailscale version?

elvisimprsntr

Finally took the plunge and installed CE 2.8.1 on a spare appliance and updated to 1.88.3_2

pkg add -f https://pkg.freebsd.org/FreeBSD:15:amd64/latest/All/tailscale-1.88.3_2.pkg

Freshports

I applied the tailscale patch. No observed issues.

Screenshot 2025-10-18 at 1.57.21 PM.png

elvisimprsntr

Updated CE 2.8.1 to 1.90.1.

There is already a .2 and .3

Changelog

pkg add -f https://pkg.freebsd.org/FreeBSD:15:amd64/latest/All/tailscale-1.90.1.pkg

Freshports

lbm_

@elvisimprsntr

Seems like only the client was updated

tailscale status
Warning: client version "1.90.1" != tailscaled server version "1.88.3"

elvisimprsntr

@lbm_

Did you restart the Tailscale daemon?

lbm_

@elvisimprsntr said in How to update to the latest Tailscale version?:

@lbm_

Did you restart the Tailscale daemon?

DOh! That fixed it :)

elvisimprsntr

Updated CE 2.8.1 to 1.90.4.

Looks like they are already working on .6

Freshports

pkg add -f https://pkg.freebsd.org/FreeBSD:15:amd64/latest/All/tailscale-1.90.4.pkg

Changelog

CarlMRoss

For pfSense+ Version 25.0.7 FreeBSD 15.0-CURRENT: I had a recent issue after upgrading Tailscale to 1.90.4 and afterwards rebooting pfSense. Tailscale would not authenticate. After researching, I found a solution and a suggested workflow for future upgrades.

First, I was able to get Tailscale to re-authenticate by executing the following commands (Tailscale Service was offline after the reboot):
service tailscaled stop
tailscale logout
sysrc tailscaled_enable="YES"
service tailscaled start
tailscale up

So that you know, here is the AI-generated one-liner for future upgrades on 25.x FreeBSD 15.0-CURRENT systems. I will test with the next available upgrade package:

"service tailscaled stop && tailscale logout || true && fetch https://pkg.freebsd.org/FreeBSD:15:amd64/latest/All/tailscale-X.Y.Z.pkg || exit 1 && IGNORE_OSVERSION=yes pkg-static add -f tailscale-X.Y.Z.pkg && rm -f tailscale-X.Y.Z.pkg && sysrc tailscaled_enable="YES" && service tailscaled start && tailscale up && tailscale version && tailscale status"

elvisimprsntr

@CarlMRoss said in How to update to the latest Tailscale version?:

upgrading Tailscale to 1.90.4 and afterwards rebooting pfSense

Although I am on 2.8.1 CE, I have never observed the problem you encountered.

All I've ever needed to do is restart the Tailscale daemon after upgrade.

CarlMRoss

@elvisimprsntr Thank you. I would not be surprised if I ended up with a lengthy solution that works but needs significant improvement.

I am using a Netgate 6100 with pfSense+, starting with version 24.x. I had updated Tailscale without trouble per this discussion by using pkg add -f https://pkg.freebsd.org/FreeBSD:15:amd64/latest/All/tailscale-x.y.z.pkg. This worked until pfSense+ version 25.0.07 (FreeBSD 15-CURRENT) and Tailscale upgrade 1.88.3.

After several attempts and web searches, I was only able to install that upgrade by using: fetch https://pkg.freebsd.org/FreeBSD:15:amd64/latest/All/tailscale-1.88.3.pkg, and then IGNORE_OSVERSION=yes pkg-static add -f tailscale-1.88.3.pkg.

Then, I could not restart Tailscale, no matter what I tried, including the sequence: service tailscaled stop, tailscale logout, service tailscaled start, and then tailscale up.

elvisimprsntr

Updated CE 2.8.1 to 1.90.6.

Freshports

pkg add -f https://pkg.freebsd.org/FreeBSD:15:amd64/latest/All/tailscale-1.90.6.pkg

Changelog

CarlMRoss

@elvisimprsntr Updated 25.0.7 to 1.90.6:

fetch https://pkg.freebsd.org/FreeBSD:15:amd64/latest/All/tailscale-1.90.6.pkg || exit 1 && IGNORE_OSVERSION=yes pkg-static add -f tailscale-1.90.6.pkg && rm -f tailscale-1.90.6.pkg

Installing tailscale-1.90.6...
package tailscale is already installed, forced install
Extracting tailscale-1.90.6: ...... done

tailscale version && tailscale status
1.90.6
long version: 1.90.6
go version: go1.25.3
Warning: client version "1.90.6" != tailscaled server version “1.90.4”

service tailscaled stop && tailscale logout || true && service tailscaled restart && service pfsense_tailscaled restart
Stopping tailscaled.
Waiting for PIDS: 3897.
Stopping tailscaled.
Waiting for PIDS: 27757.
tailscale 42315 - - Waiting for device tailscale0
tailscale 43079 - - Found device tailscale0
tailscale 43473 - - Added tailscale0 to interface group Tailscale
tailscale 43659 - - Bringing up tailscale0 with --auth-key=tskey-auth-xxxxxxxxxxxxxxxx --login-server=https://controlplane.tailscale.com
backend error: invalid key: API key does not exist

service tailscaled stop && tailscale logout || true && service tailscaled start && tailscale up && tailscale version && tailscale status
Stopping tailscaled.
Waiting for PIDS: 41895.
1.90.6
long version: 1.90.6
go version: go1.25.3
Success!