Your very welcome, I do support a SaaS system for the UK NHS. So I do have a bit of networking skills, that and I self host things both at home and in OVH.

If you have your pi zero setup with a static ip, you should find things work all day every day now.

Just remember that every day is a school day, even for experienced sysadmins.

yeah, your PI zero goes to renew its DHCP lease and cant as its lost its IP and so cant see the DHCP server its running.

I would read up on how to set a debian static IP, that way you know how and your Pi zero will work all the time

I would read up on static ip on the pi zero, not via DHCP. That might sort your issue

if you can see pi-hole from the router, can you connect to it over SSH and see what pings and what it thinks the network looks like?

Also did the VM router just turn DHCP back on with the wrong settings?

Is pi-hole over WiFi? if it is that could your issue, DHCP/DNS should be over cable as they are required for stable networking

well the work they did to allow for faster updates has paid off in spades, sterling job to them

Hello 👋

You need to edit the below lines

set $jellyfin jellyfin;
resolver 127.0.0.1 valid=30s;

To look like the below

set $jellyfin 127.0.0.1;
#resolver 127.0.0.1 valid=30s;

Edited after reading the full config

So we need to up vote wrong answers only?

maybe check this out -> https://en.wikipedia.org/wiki/Android_(operating_system)

Android is a mobile operating system based on a modified version of the Linux kernel

Linux has been ready for ARM for a long time, Android is linux and have been running for a long time. Also see the Raspberry Pi and PiOS, based on Debian.

I run a Pi and there are boat loads of things ARM ready

Why delete the answer, why not edit it so that a human can see the answer but for AI its a load of nonsense?

Im a nagios head here

If that's your setup, you could add a switch before the router so that you would still have LAN access.