Matrix as adequate but not easy to set up. Their encryption dance is terrible and bites you eventually. However, the install is top notch if you have a server you can dedicate to it and are familiar with editing flatfiles and running commands. Literally all kinds of difficult addons enabled with a config option.

https://github.com/spantaleev/matrix-docker-ansible-deploy

Are you routing DNS over wireguard the whole time or do the DNS servers change when you go from public internet to your home network?

If you are using the same DNS servers i.e. always using DNS over wireguard then there isn’t really a lot you can do.

The way I do this is when I am on my home network I use the DNS on that network, i.e. the adguard instance I set up and also override DNS names with, when I am on some public internet i.e. via cellular, I use whatever DNS server they have. So on home network jellyfin.bob.com returns 192.168.8.3 (for example) and on the public internet jellyfin.bob.com will return 68.32.23.11 (i.e. my public IP address).

However that requires multiple DNS servers.

What is an example server where you’d like to do this (it may give us more options) and how is your DNS set up?

Your home router knows nothing about your wireguard VPN unless it is also configured to be a peer in it. So in short no it will not recognize and route your connection locally unfortunately.

Are you using TLS here at all? Can you give me an example of how you access this on your phone when remote vs when local.

e. g. From my phone on cellular I go to Firefox and type in jelly.bob.com which resolves to my wireguard ip hitting the VM in the cloud that then using nginx as a reverse proxy to reach jellyfin over my network.

Remote network: jellyfin.bob.com Phone - > VM - > Home Server where Jellyfin is running

Is each hop is over wireguard i.e from phone to VM from VM to Home Server?

On the local network: jellyfin.bob.com Currently looks the same as the above and what youx like it to do with the same name is go: Phone->Home server

Even when wireguard is on, correct?

DNS server you use from your home network retuns 192.168.1.20 for your service hosted at jellyfin.Bob.org

The DNS server you hit when publically looks up jellyfin.Bob.org and gets the IP from the nameserver you have set with your domain registrar often just theirs and you set this to your home WAN ip.

You have to configure both. I use opentofu / terraform to configure both all from the CLI. Any software like DNS that has a bunch of implementations that doesn’t have Open-Tofu support gets skipped and an alternative is found at this stage. You just can’t beat config as code for this type of set up.

You can also use NAT reflection which will effectively reroute the connection from within your network to your external IP to work on your local network.

I started with reflection and ended up going to the multiple DNS servers as it felt cleaner and I already was running Adguard so why not.

Both adguard and pihlle have opentofu modules.

Rereading your post (heh): In your case I’d just always serve over the wireguard ip local or not. Why do you want to use the local IP vs wireguard? The overhead of wireguard is pretty low