Mac OS 10.14.6 not using /etc/resolver/test

I have a dns server running on the host in a virtual machine with the IP 192.168.99.169

If I run the dns queries I get these responses

dig:

dig @192.168.99.169 hello-john.test

result:

;; Warning: Message parser reports malformed message packet.

; <<>> DiG 9.10.6 <<>> @192.168.99.169 hello-john.test
; (1 server found)
;; global options: +cmd
;; Got answer:
;; ->>HEADER<<- opcode: QUERY, status: NOERROR, id: 43698
;; flags: qr rd ra ad; QUERY: 1, ANSWER: 1, AUTHORITY: 0, ADDITIONAL: 1
;; WARNING: Message has 8 extra bytes at end

;; QUESTION SECTION:
;hello-john.test.       IN  A

;; ANSWER SECTION:
hello-john.test.    300 IN  A   192.168.99.169

;; Query time: 17 msec
;; SERVER: 192.168.99.169#53(192.168.99.169)
;; WHEN: Sun Sep 29 09:50:18 CDT 2019
;; MSG SIZE  rcvd: 73

nslookup:

nslookup hello-john.test 192.168.99.169

result:

Server:     192.168.99.169
Address:    192.168.99.169#53

Non-authoritative answer:
Name:   hello-john.test
Address: 192.168.99.169

Everything works correctly for the dns server. If I update the dns servers on the mac so that the only dns server is 192.168.99.169 then things also work the same way but I don't have to specify the dns server. For example:

Update the dns servers

networksetup -setdnsservers Wi-Fi 192.168.99.169

dig:

dig hello-john.test

;; Warning: Message parser reports malformed message packet.

; <<>> DiG 9.10.6 <<>> hello-john.test
;; global options: +cmd
;; Got answer:
;; ->>HEADER<<- opcode: QUERY, status: NOERROR, id: 6173
;; flags: qr rd ra ad; QUERY: 1, ANSWER: 1, AUTHORITY: 0, ADDITIONAL: 1
;; WARNING: Message has 8 extra bytes at end

;; QUESTION SECTION:
;hello-john.test.       IN  A

;; ANSWER SECTION:
hello-john.test.    300 IN  A   192.168.99.169

;; Query time: 7 msec
;; SERVER: 192.168.99.169#53(192.168.99.169)
;; WHEN: Sun Sep 29 09:57:10 CDT 2019
;; MSG SIZE  rcvd: 73

nslookup:

nslookup hello-john.test

result:

Server:     192.168.99.169
Address:    192.168.99.169#53

Non-authoritative answer:
Name:   hello-john.test
Address: 192.168.99.169

Completely overriding the dns servers does not work for me since need to have multiple ip addresses that are searched.

I reset the dns servers to a normal dns server.

networksetup -setdnsservers Wi-Fi 8.8.8.8

I create a file /etc/resolver/test with the contents:

domain test
nameserver 192.168.99.169
search_order 1
timeout 5

I can test that the resolver was loaded correctly with scutil:

scutil --dns

result:

DNS configuration

resolver #1
  nameserver[0] : 8.8.8.8
  flags    : Request A records
  reach    : 0x00000002 (Reachable)

resolver #2
  domain   : local
  options  : mdns
  timeout  : 5
  flags    : Request A records
  reach    : 0x00000000 (Not Reachable)
  order    : 300000

resolver #3
  domain   : 254.169.in-addr.arpa
  options  : mdns
  timeout  : 5
  flags    : Request A records
  reach    : 0x00000000 (Not Reachable)
  order    : 300200

resolver #4
  domain   : 8.e.f.ip6.arpa
  options  : mdns
  timeout  : 5
  flags    : Request A records
  reach    : 0x00000000 (Not Reachable)
  order    : 300400

resolver #5
  domain   : 9.e.f.ip6.arpa
  options  : mdns
  timeout  : 5
  flags    : Request A records
  reach    : 0x00000000 (Not Reachable)
  order    : 300600

resolver #6
  domain   : a.e.f.ip6.arpa
  options  : mdns
  timeout  : 5
  flags    : Request A records
  reach    : 0x00000000 (Not Reachable)
  order    : 300800

resolver #7
  domain   : b.e.f.ip6.arpa
  options  : mdns
  timeout  : 5
  flags    : Request A records
  reach    : 0x00000000 (Not Reachable)
  order    : 301000

resolver #8
  domain   : test
  nameserver[0] : 192.168.99.169
  timeout  : 5
  flags    : Request A records
  reach    : 0x00020002 (Reachable,Directly Reachable Address)
  order    : 1

DNS configuration (for scoped queries)

resolver #1
  nameserver[0] : 8.8.8.8
  if_index : 5 (en0)
  flags    : Scoped, Request A records
  reach    : 0x00000002 (Reachable)

However when I run dig or nslookup it is not using the resolver. I am guessing this has something to do with the order that the resolver configs are used.

dig:

dig hello-john.test

result:

; <<>> DiG 9.10.6 <<>> hello-john.test
;; global options: +cmd
;; Got answer:
;; ->>HEADER<<- opcode: QUERY, status: NXDOMAIN, id: 39721
;; flags: qr rd ra ad; QUERY: 1, ANSWER: 0, AUTHORITY: 1, ADDITIONAL: 1

;; OPT PSEUDOSECTION:
; EDNS: version: 0, flags:; udp: 512
;; QUESTION SECTION:
;hello-john.test.       IN  A

;; AUTHORITY SECTION:
.           86388   IN  SOA a.root-servers.net. nstld.verisign-grs.com. 2019092900 1800 900 604800 86400

;; Query time: 16 msec
;; SERVER: 8.8.8.8#53(8.8.8.8)
;; WHEN: Sun Sep 29 10:06:50 CDT 2019
;; MSG SIZE  rcvd: 119

nslookup:

nslookup hello-john.test

result:

Server:     8.8.8.8
Address:    8.8.8.8#53

** server can't find hello-john.test: NXDOMAIN

If I turn off my Wi-Fi I just see that resolver #1 from scutil --dns just shows as

DNS configuration

resolver #1
  flags    : 
  reach    : 0x00000000 (Not Reachable)

I believe I am missing some configuration in /etc/resolver/test but I cannot find a way to make sure it gets used.

Thanks for your help!

Even though nslookup and dig do not return a correct response it seems that I can still ping the host

ping:

ping hello-john.test

result:

PING hello-john.test (192.168.99.169): 56 data bytes
64 bytes from 192.168.99.169: icmp_seq=0 ttl=64 time=0.259 ms
64 bytes from 192.168.99.169: icmp_seq=1 ttl=64 time=0.390 ms

This works good enough for my purposes