this post was submitted on 13 May 2026
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I want to preface this with the fact that I am definitely NOT a networking expert so... don't trust anything I say.
My situation is a bit different because I am using Tailscale, though I have it on the list to be replaced in the future.
When you Wireguard to your LAN, do subsequent DNS requests go through the VPN? Sounds like you're looking into that route based on your third point above. If so, can you just add a static DNS resolution to your LAN router that points to your Caddy SSL terminator/reverse proxy? This assumes a static IP for your host.
That's what I've done. On my router I've set a static DNS entry of
silverbullet.mydomain.com -> 10.0.0.101(where*.101is the static IP of my internal host/Caddy). This allows everything to resolve correctly when I'm physically attached to my LAN but also when connecting remotely via Tailscale.It may not be elegant, but it avoids the hassle / extra config of a local DNS server as well as the need to manage host routes on each device.
EDIT: My router is running OpenWRT but I think most consumer grade routers support static DNS routes... but I could be wrong.