I have followed that guide which let me to a few GitHub issues.

Here is what I have put in my config:

servers {
        trusted_proxies cloudflare {
                        interval 12h
                        timeout 15s
                }
        trusted_proxies static private_ranges
        client_ip_headers Cf-Connecting-Ip X-Forwarded-For
        }
}

I have also added all Cloudflare IPs in Jellyfin's known proxies:

103.21.244.0/22, 103.22.200.0/22, 103.31.4.0/22, 104.16.0.0/13, 104.24.0.0/14, 108.162.192.0/18, 131.0.72.0/22, 141.101.64.0/18, 162.158.0.0/15, 172.64.0.0/13, 173.245.48.0/20, 188.114.96.0/20, 190.93.240.0/20, 197.234.240.0/22, 198.41.128.0/17

Yet, I'm still not seeing the real IPs.

That led me in the right direction!

Fixed it with:

pvresize /dev/sda3

lvresize --extents +100%FREE --resizefs /dev/pve/data

Thank you!

Would you know how I would go about doing that?

I'll give that a shot with gparted on the weekend if all else fails. Thanks!

They had a server breach and didn't tell anyone until a few years after the fact.

PiHole can't specify specific ports for each cname, which is what you need a reverse proxy for.

Typically, you create all of your cnames in pihole and direct them to your reverse proxy server IP. From your reverse proxy of choice, you specify each url to the specific ip:port of your service.

Awesome! Thank you

Wait... How do you make SearXNG redirect to old.reddit?

You will need to run a reverse proxy on one of your VMs ( I use Caddy, it's very simple), and forward port 80/443 to your reverse proxy.

Within your reverse proxy, you can tell it what port corresponds to which address and it will send you to the right service.

This is obviously an oversimplified answer, but there are many Caddy guides and I can help you with any specific questions.

I mean, the world's your oyster with price limit! Haha.

That's very normal regarding the crash trying to join #matrix:matrix.org. You need much higher specs and need to be using Postgres database, MySQL probably won't handle it.

Can you post a sanitized version of your homeserver.yaml so we can take a look at your config?

Also are you running docker or something else?

To me it sounds like you don't have a DHCP problem at all, the issue is no website can be resolved when your DNS is down (PiHole).

You really have two options:

1. Make sure the PiHole stays up 24/7, with minor downtime for maybe a reboot or an update.

or

2. Setup an additional raspberrypi with PiHole and use gravity-sync to keep them synced. Then, I would run ISC-DHCP server on both the raspberrypi's, one as the primary and the other as the secondary. That way you can specify both of your DNS servers. Make them authoritative and disable your routers DHCP. You can take a look at this guide:

https://stevendiver.com/2020/02/21/isc-dhcp-failover-configuration/

Personally, I like to keep the wife happy so I have option 2 at home, that way the internet never goes down when I tinker.

Edit: Didn't notice you said your router can't issue out two DNS servers. I've never heard of that.