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I have the (more or less) same setup. Your DNS entries on your pihole instance should point to the local ip of your server (192.168.x.x).
If thats the case check the dns settings of your router. Under DHCP settings there should be a input field for your dns server. This has to be the local IP of your pihole.
One thing you could do to start diagnosing the Problem is running this command:
nslookup servicename.yourdomain.tld
. This should return your local IP and not a public one.How do you determine that the requests are leaving your Network?
When I use tracert I can see the package going through a server in Frankfurt which is definetely outside of my local network. The final IP address that tracert shows me is from a cloudflare server in california (2606:4700:3033::ac43:b10f) according to this site: https://whatismyipaddress.com/ip-lookup
Using nslookup for my domain I get 3 addresses. The first two are cloudflare addresses in the US. The final one is my servers local IP address.
Pihole seems to upstream your requests although there is a local entry for that domain in your settings. Maybe it has something to do with using IPv6? Maybe your device prefers the cloudflare IPv6 over your local IPv4 address.
Or Maybe your device queries your pihole as well as your Router to get the IP. Check your current dns server on your device:
ipconfig /all
(Windows)Looking at the output of that command I get the following for my ethernet network interface
Using nslookup on that IPv4 address tells me that all of those addresses are pointing to my pi-hole
I've added another local DNS entry on my Pi-Hole which points the domain I use to the same server but this time uses its IPv6 address. That doesn't seem to help though or it takes some time to update. I flushed the DNS cache on my machine after adding this entry though.
I think I fixed the issue by enabling the
Never forward reverse lookups for private IP ranges
option in Pi-Hole. After that I flushed my dns cache again and called tracert for my domain name. I only get one hop directly to my server now. nslookup also shows only local addresses now.