How To - Install Tailscale on PFSense
Tailscale is an overlay VPN that allows you to create a VPN like tunnel into one or more of your networks. For a person like me who likes to self-host applications but doesn’t want to deal with all the security concerns of putting those on the internet, it’s a lifesaver.
How To Install Tailscale Plugin In PFSense
In the PFSense menu, go to:
System / Package Manager / Available PackagesSearch for Tailscale and hit the install button. Tailscale will show up in the VPN drop-down menu.
Once you have verified that the tailscale plugin has been successful click on the drop-down menu and select:
VPN / Tailscale
Log into tailscale and go to:
Settings / Keys / Generate Auth Key...
https://login.tailscale.com/admin/settings/keys
Take the output of the key and paste it into PFsense
If you go back to Tailscale, you should see that PFSense is there now
In the “…” menu above for PFSense, you can set the expiry to disabled. This allows you to still use the “run once” key that will only work on this one device, and not have to worry about replacing it unless you specifically want to.