Hi srwjiwate,
Can you replicate this from a source client that is not connected to any Meraki infrastructure or Cisco Umbrella?
I suspect the following is happening. The pen testing tool is sourcing from a network that uses Meraki infrastructure that has Cisco Umbrella enabled. When it DNS queries, the Meraki infra hijacks the DNS request and sends to Umbrella. Umbrella resolves and replies to the meraki infras, which re-writes the DNS response to look like it came from the proper name server. Here is an example of me asking non-existent name servers to resolve different names and they work
U:\>nslookup abc.com 86.75.30.9
Server: UnKnown
Address: 86.75.30.9
Non-authoritative answer:
Name: abc.com
Addresses: 3.162.3.125
3.162.3.49
3.162.3.100
3.162.3.119
U:\>nslookup cbs.com 1.2.3.4
Server: UnKnown
Address: 1.2.3.4
Non-authoritative answer:
Name: cbs.com
Addresses: 2600:1901:0:626a::
34.149.41.86
U:\>nslookup nbc.com 7.0.0.56
Server: UnKnown
Address: 7.0.0.56
Non-authoritative answer:
Name: nbc.com
Addresses: 23.223.17.138
23.223.17.140
Here is Umbrella resolving them:

if you wireshark capture on your penteset tool everything looks normal, even though it is weird AF. But if you capture on your remote MX WAN interface, you won't see any of these DNS requests get there.
It's a tricky one. Let me know if that makes sense.