I’m finally starting to install local web apps that my wife/kids would be interested in, and I know it has to be super easy or they’re never going to go near it. Most everything is running on my Synology on different ports, with absolutely nothing exposed to the outside world, and I’d like to run local DNS and proxy so everything is available LAN-only with an easy hostname - plex.local, paperless.local, etc. (If we want remote access I’ll just run Tailscale.) I’m already running PiHole, and I’m assuming if I poke around I can add local names in there, but has anybody else that’s done this have any suggestions for setting things up?

As recommended by others, you might want to use a real public domain that you own, and a reverse proxy for split horizon DNS. I personally run Bind9, Unbound, and PiHole as my DNS servers. Bind9 handles split horizon, so if I request my domain internally it gets routed through Bind. Then bind hands it off to PiHole for adblocking, and PiHole makes requests through Unbound set up as a recursive DNS server which doesn’t rely on any external DNS. I also use Traefik as a reverse proxy for all of my services. My set up is more complicated than necessary, and if you want just a few local domains, PiHole + a reverse proxy is plenty good for your needs.

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