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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.
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.
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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.
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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.
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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.