Hostname resolution

I've seen and read several posts on this and the majority of what I read was "switch to pihole DHCP" or "modify /etc/hosts/ on the machine". The latter of the two being incredibly in unideal I switched from my router controlled DHCP to pihole. On doing that it seemed like all hostnames were ignored and I could only access things via ip; I switched back.

I'm feeling kinda hopeless. I know it seems trivial to use hostnames over IP but when you have a family as big as I do and the amount of people coming in and out of the network as I do you really want to simplify everything for the end user.

With pihole filtering my main use case here, how the heck am I supposed to arrange my network settings so that hostnames are viable?

We offer a built-in Local DNS page where you can map host names to IP's.

After above switching, did you renew the DHCP leases on involved clients?

Disconnecting them from network and reconnect will do that usually.
Otherwise reboot involved clients.

EDIT: And use the nslookup tool on a client (Windows/MacOS/Linux) to test eg:

C:\>nslookup hakpc
Server:  pi.hole
Address:  10.0.0.2

Name:    hakpc.home.dehakkelaar.nl
Address:  10.0.0.11

Check if your router is capable of correctly answering DNS requests for local hosts, e.g. by running

nslookup <de.vi.ce.ip> <ro.ut.er.ip>

Substitute <de.vi.ce.ip> and <ro.ut.er.ip> as appropriate (e.g. nslookup 192.168.0.42 192.168.0.1).
Your router should answer with a hostname for your device.

If it does, you could try to enable Pi-hole's Conditional Forwarding via Settings | DNS.

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