How to Setup The Tailscale VPN and Routing on pfsense [YouTube Release]

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:stopwatch: Timestamps :stopwatch:
00:00 pfsense tailscale pacakge
03:31 Headscale server
04:19 Tailscale Web Management
05:26 Tailscale Access Contol Security
06:10 Managing Tailscale in pfsense
09:36 pfsense routes and exit node
10:48 Tailscal Connectivity and Firewall Security

2

Hi Tom, are you able to update your video, as I was trying to get Tailscale to work on 2.7.2 and the latest PFSense+ and discovered they’ve changed the way outbound NAT works for the Tailscale setup - Even documentation on the Tailscale PFsense setup installation hasn’t updated.

Here’s the URL to the issue that discusses that change after many reported having the same issue - Regression #14987: ``Interface Address`` is no longer an option for outbound NAT targets - pfSense - pfSense bugtracker

So, far I haven’t been able to test Tailscale in a non-production environment to see if there’s a viable workaround.

Was wondering if you’re aware of any to get outbound NAT with Tailscale working?

1 Like
3

Would this be what’s causing me not to be able to get a direct connection behind my pfSense box on my local network from externally devices (my laptop sitting at a coffee shop)? Doing a tailscale ping test it has to relay through a DERP server to reach my internal network devices, which results, obviously, in much slower speeds.