A friend of mine recently setup a new network after moving into his new house, in doing so, he decided to setup pihole for the first time.
He installed pihole on a raspberry pi, and configured it and that is when he ran into trouble and asked me (I am far far far from an expert).
I figured out that that the issue is dns.listening mode set to local.
If I change the setting to either Single or All, the pihole works as expected, but when set to the default of local, it does not work. The problem is that the description said that either Single or All are dangerous, so that scared me away from using them.
His network has a number of VLANs with the pihole being in a VLAN with other servers if that makes a difference.
I have a relatively similar setup and I never had to adjust the dns.listening mode, but I installed my pihole over 6 years ago now, so maybe things have changed.
Thanks for any insight.