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points by swingandamiss 2 days ago | 0 comments

With AI, the complexity doesn't really matter anymore. Codex or Claude can easily configure complex site-to-site setups and peer configurations on mobile devices. I did this by hand before and it was hard and difficult to get right. Now I just tell AI and it does so perfectly, checks and verifies things. AI made life so easy.

[–] drum55 2 days ago

No amount of claude can handle the key thing that Tailscale fixes about wireguard, all of the connection to connection logic is handled be it direct, via all sorts of weird hole punching or via relays. Wireguard itself is horrible to do this with, half the time you're just looking at `wg status` wondering why the packet counter isn't incrementing today. It can never achieve the magic that is a direct connection between plane wifi and a host that's behind NAT on the ground.

[–] hdgvhicv 2 days ago

I can’t think of a single time I’ve wanted to connect between two hosts when I haven’t specifically allowed one through a firewall

[–] drum55 2 days ago

NAT are not firewalls.

[–] hdgvhicv 1 day ago

Functionally they are. Allow traffic aiming at this address and this port to arrive on this server.

Not that my WireGuard connection needs nat as it terminates on my router. And I use private ip ranges as I want to be sure that if WireGuard drops out for some reason traffic doesn’t route over the unencrypted path. Defence in depth.

[–] arcanemachiner 2 days ago

This is true, but I still wouldn't discount the possibility of mistakes. It's good to know how your home network works. Even Opus 5.5 can make some pretty dumb mistakes, particularly if it doesn't have the full picture.

[–] swingandamiss 2 days ago

Humans also make mistakes. At this point, I trust AI more than humans when it comes to casually configuring VPNs. I've read many who exposed things by mistake on reddit. AI has nearly solved this, probably is a solved issue at this point.

[–] femiagbabiaka 2 days ago

I would not personally expose my devices over a VPN that I self-hosted and set up purely through AI unless I felt like I understood how it worked completely. But that's probably just personal paranoia.

[–] swingandamiss 2 days ago

Just go read reddit threads on people who do this by hand following half baked guides. There's a huge population doing this, now everyone is switching to AI. It's a big win and safer. Not everyone is a trained network engineer, but now they are with AI

[–] LeBit 2 days ago

It makes no sense at all to configure a >3 nodes wireguard setup with straight wireguard.

Wireguard is the building block for higher level tools like Tailscale to build on.