How to update to the latest Tailscale version?

elvisimprsntr

Better to update your pfSense since this version is EOL:
https://docs.netgate.com/pfsense/en/latest/releases/versions.html#id19

I work remotely 6-7 days a week and can't afford any issues without testing first and having the ability to roll back. I have a cold spare appliance I can physically swap out. I typically wait for a long holiday weekend.

Also not pleased about the lack of an offline installer image. Makes the offline restore a lot more complicated

Install 2.7.2 using offline image with current config.xml on flash drive
Upgrade to 2.8.1 in place.

lbm_

@veddy254 Replaced by _1 already

pkg add -f https://pkg.freebsd.org/FreeBSD:15:amd64/latest/All/tailscale-1.88.3_1.pkg

Wolf666

I am receiving this trying to update:
ld-elf.so.1: Shared object "libutil.so.10" not found, required by "pkg"
I am on pfSense 25.07.1, it is the first time I see it, I never had issues updating manually.

CarlMRoss

@Wolf666, I have the same version as you and the same problem. Found this solution with Grok:

fetch https://pkg.freebsd.org/FreeBSD:15:amd64/latest/All/tailscale-1.88.3_1.pkg

IGNORE_OSVERSION=yes pkg-static add -f tailscale-1.88.3_1.pkg

It may be possible to do it in one step,
IGNORE_OSVERSION=yes pkg-static add -f https://pkg.freebsd.org/FreeBSD:15:amd64/latest/All/tailscale-1.88.3.pkg

Wolf666

@CarlMRoss Thanks, it worked! I cannot give you a thumb-up because I am not allowed.

CarlMRoss

@Wolf666, Thumbs up to Grok AI. It beat ChatGPT and Claude to the answer from the start.

elvisimprsntr

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

Changelog

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!

mightykong

@CarlMRoss I've followed your very helpful instructions and got mine updated to 1.90.6. However, I did notice that tailscale does not start on reboot. Is this still happening for you as well? I can get it restarted with the commands you provided but having to do that manually is a concern.

CarlMRoss

@mightykong Yes, my system also requires a restart after reboot, and what has worked for me is:

service tailscaled stop && tailscale logout || true && service tailscaled start && tailscale up

What has worked for updates included a [sysrc tailscaled_enable="YES"] that is supposed to handle tailscale restart after reboot, but it has not worked for me. I am looking into it, and others will be as well. In the meantime, this is my update one-liner command line:

service tailscaled stop && tailscale logout || true && 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 && service tailscaled start && tailscale up

Options: add && tailscale version && tailscale status to automate a first check; and, the "rm -f tailscale-1.90.6.pkg" is not needed, but once I saw the suggestion, I decided to keep it.

luckman212

@mightykong @CarlMRoss Looks like you might be experiencing https://github.com/tailscale/tailscale/issues/17793

I also have a 6100 + Tailscale 1.90.6 so I will test mine now.

update: I don't seem to be having this problem, which is odd because I'm usually that one guy in a thousand who has the strange bug that nobody else can reproduce.

Have you tried deleting the contents of /usr/local/pkg/tailscale/state ?