Jun 6 01:59:03 dnsmasq: cached is NXDOMAIN Jun 6 01:59:04 dnsmasq: validation result is INSECURE Jun 6 01:59:04 dnsmasq: reply is NXDOMAIN I did upgrade the router 2 days ago, I saw that an update was available and I did it hoping it would fix the issue by itself. It highly points at a configuration issue on the Router I did see this behavior before and it always had to to with the router that played tough to get and didn't allow 53 traffic to be relayed with the network (fear of OpenResolver). I understand the complexity of your network and using Pi-hole as the default DHCP server right now, ever for testing, is a bit of a pain. The DNS request originates from the client, and it hits the router, despite the DNS option set at DHCP server lever. The problem is with the request not reaching it the right way. Pi-hole based on your debug log, is working as expected. The only thing I can think of is somewhere, the query gets intercepted and. What IP shows as originating from in the log ? The nslookup still shows the same thing ? See if changing the listening behavior changes anything but I highly doubt that as it shouldn't be related at all. Your Pi-hole is set to listen to queries on eth0.
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