How to update to the latest Tailscale version?
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@elvisimprsntr said in How to update to the latest Tailscale version?:
Updated CE 2.7.2 to 1.88.3_1
Better to update your pfSense since this version is EOL:
https://docs.netgate.com/pfsense/en/latest/releases/versions.html#id19 -
Latest for CE 2.8.x as of October 10th, 2025: Tailscale 1.88.3
pkg add -f https://pkg.freebsd.org/FreeBSD:15:amd64/latest/All/tailscale-1.88.3.pkg -
Better to update your pfSense since this version is EOL:
https://docs.netgate.com/pfsense/en/latest/releases/versions.html#id19I 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.
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@veddy254 Replaced by _1 already
pkg add -f https://pkg.freebsd.org/FreeBSD:15:amd64/latest/All/tailscale-1.88.3_1.pkg -
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. -
@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 -
@CarlMRoss Thanks, it worked! I cannot give you a thumb-up because I am not allowed.
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@Wolf666, Thumbs up to Grok AI. It beat ChatGPT and Claude to the answer from the start.
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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.pkgI applied the tailscale patch. No observed issues.
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Updated CE 2.8.1 to 1.90.1.
There is already a .2 and .3
pkg add -f https://pkg.freebsd.org/FreeBSD:15:amd64/latest/All/tailscale-1.90.1.pkg -
Seems like only the client was updated
tailscale status Warning: client version "1.90.1" != tailscaled server version "1.88.3" -
Did you restart the Tailscale daemon?
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@elvisimprsntr said in How to update to the latest Tailscale version?:
Did you restart the Tailscale daemon?
DOh! That fixed it :)
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Updated CE 2.8.1 to 1.90.4.
Looks like they are already working on .6
pkg add -f https://pkg.freebsd.org/FreeBSD:15:amd64/latest/All/tailscale-1.90.4.pkg -
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 upSo 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"
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@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.
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@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.
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Updated CE 2.8.1 to 1.90.6.
pkg add -f https://pkg.freebsd.org/FreeBSD:15:amd64/latest/All/tailscale-1.90.6.pkg -
@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: ...... donetailscale 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 existservice 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! -
@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.
