Mac Ventura 13.4 DNS split-horizon - ping doesn't work but dig does

Question

What's the problem:

• dig, nslookup can resolve domains using PiHole dns server
• ping, browser etc. can't

What I tried to do:

• reboot :d
• flush cache (sudo dscacheutil -flushcache; sudo killall -HUP mDNSResponder)
• add/remove wildcard entries from the registrar
• use second level domain or subdomain (hmwsl.de vs int.hmwsl.de)
• add a DNS server entry in network settings apart from DHCP sudo networksetup -setdnsservers "Wi-Fi" 192.168.69.10 this worked

So the immediate questions are:

• why DHCP-given DNS resolvers are not enough?
• how dscacheutil and friends actually work?

What I want:

• reach my raspberry-pi services either from afar or from home LAN
• use a single domain name (with subdomains)to ease authentication with Authelia
• have a single Authelia instance
• use proper Let's Encrypt certificates
• use Traefik as a reverse proxy

What I did:

• got a domain
• set up Traefik, Authelia and a few services (they do work with a .local domain with Avahi)
• set up PiHole with a wildcard DNS entry for the domain (see below)

What's going on:

Dig and nslookup resolve the (wildcard) domain:

➜ dig foo.int.hmwsl.de

; <<>> DiG 9.10.6 <<>> foo.int.hmwsl.de
;; global options: +cmd
;; Got answer:
;; ->>HEADER<<- opcode: QUERY, status: NOERROR, id: 2173
;; flags: qr aa rd ra; QUERY: 1, ANSWER: 1, AUTHORITY: 0, ADDITIONAL: 1

;; OPT PSEUDOSECTION:
; EDNS: version: 0, flags:; udp: 1232
;; QUESTION SECTION:
;foo.int.hmwsl.de.      IN  A

;; ANSWER SECTION:
foo.int.hmwsl.de.   0   IN  A   192.168.69.10

;; Query time: 40 msec
;; SERVER: 192.168.69.10#53(192.168.69.10)
;; WHEN: Tue Jul 18 15:11:12 CEST 2023
;; MSG SIZE  rcvd: 61

➜ nslookup bar.int.hmwsl.de
Server:     192.168.69.10
Address:    192.168.69.10#53

Name:   bar.int.hmwsl.de
Address: 192.168.69.10

But ping and Mac utils doesn't:

➜ ping foo.int.hmwsl.de
ping: cannot resolve foo.int.hmwsl.de: Unknown host

➜ dscacheutil -q host -a name foo.int.hmwsl.de && echo end
end

❯ dns-sd -q foo.int.hmwsl.de
DATE: ---Tue 18 Jul 2023---
15:15:07.504  ...STARTING...
Timestamp     A/R  Flags         IF  Name                          Type   Class  Rdata
15:15:07.505  Add  40000002       0  foo.int.hmwsl.de.             Addr   IN     0.0.0.0    No Such Record
^C

I think my local DNS is configured properly:

➜ scutil --dns
DNS configuration

resolver #1
  nameserver[0] : 192.168.69.10
  nameserver[1] : 62.233.233.233
  nameserver[2] : 8.8.8.8
  if_index : 12 (en0)
  flags    : Request A records
  reach    : 0x00020002 (Reachable,Directly Reachable Address)

Also ping from the raspberry-pi works alright:

$ ping baz.int.hmwsl.de
PING baz.int.hmwsl.de (192.168.69.10) 56(84) bytes of data.
64 bytes from pi-hole.int.hmwsl.de (192.168.69.10):

And the relevant entry in PiHole:

$ cat pi-hole/etc/dnsmasq.d/02-local-wildcard-dns.conf
address=/int.hmwsl.de/192.168.69.10

Answer 1

Same issue here with any iOS/macOS device. I am using Synology DNS Server and facing the same issue! Windows systems have no issue!

Getting crazy