Updated CE 2.7.2 to 1.86.2_1 Changelog pkg add -f https://pkg.freebsd.org/FreeBSD:14:amd64/latest/All/tailscale-1.86.2_1.pkg Freshports

@totalimpact Tailscale 1.54.0 is 2+ years out of date. Tailscale has made quite a number of changes since Tailscale 1.54.0, likely rendering it incompatible with their servers. I would consider manually updating the Tailscale FreeBSD package. FreshPorts does not maintain an archive of all the releases, only the latest compiled by the volunteer maintainers. The key to manually upgrading is knowing which FreeBSD version your pfSense release is running, i.e. 14 or 15. You can following along here.

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.

@Gertjan said in can I install a FreeBSD 14 pkg on a FreeBSD 15 pfSense?: If the package contains binaries : forget it. The ABI is different. It's not a hard and fast rule like that. It depends upon what the binary is, what dependencies it has, and how everything was compiled. I am currently running a binary package, which was built on FreeBSD 14.2-RELEASE, on pfSense 25.07 (FreeBSD 15.0-CURRENT) without issue.

Any luck getting this fixed? I am running into the exact same issue with my setup. Latest Headscale (0.26.1), PFSense 2.7.2, and Tailscale package 1.84.2 installed on PfSense.

@maxpol @TravisH Did you get this resolved? I have th esame issues or very similiar. The first tailnet client works, then when i add additional ones they sometimes work, but majoritvly they fail. PFSense+ latest f/w. All endpoint showing online in tailscale status within pfsense and also on the tailscale portal. Thanks

Thank you, @elvisimprsntr, I did that and it worked beautifully.

From TS support "I’m Kelly from the Tailscale support team. Thanks for reaching out! This is a common point of confusion- Even with the “Key Expiry: Disabled” option selected in the Tailscale web UI, that only applies to machines authenticated via the web login. You need to generate a Reusable, Ephemeral = false, Pre-Auth Key via the Tailscale admin panel, and use that on the pfsense."

@Gertjan Thanks for the reply! Thats what I was afraid of. We have 100s of pfsense/tailscale nodes that we don't have UI access to. We use Ansible to automatically configure them in a remote fashion, everything was fine until this routes issue. But I will check out the link. Thanks again!

@DavcoreTech Looks like you may be running an older version of pfSense and/or Tailscale. You might want to upgrade to latest version (1.78.1) on all clients, which may resolve some of the connection issues. Although, Netgate has not updated the Tailscale package in some time, you can manually update How to update to the latest Tailscale version? You may also want to upgrade Windows 8.1, which MS officially stopped supporting on January 10, 2023