Struggling with DNS Wildcard Not Resolving Subdomains

Hey everyone,

I’m hoping someone here can help me out because I’ve been banging my head against this DNS issue for a while now, and I’m running out of ideas.

Before we start do note that my internal DNS server connects to my EC2 instances via OpenVPN and its working fine. thus what im trying to do here letting the ec2 instances use my on-prem dns server as for some web apps running localy from other development teams. They can ping each other normally using there private ip address range.

What I’m Working With:

  • I’ve got an internal DNS server (Windows Server) running locally on-prem.
  • There’s a wildcard DNS record (*.test.this.local) set up, pointing to 10.2.1.174
  • The idea is that any subdomain under test.this.local  (e.g., wildcarduse.test.this.local) should resolve to that IP without needing specific entries for each one. (hence why the wildcard use right?)

What’s Happening:

  • For some reason, wildcarduse.test.this.local isn’t resolving.
  • If I use nslookup, it works fine, but when I try to ping it (or use anything else that relies on DNS resolution), I get this error:

Ping request could not find host wildcarduse.test.this.local Please check the name and try again.

  • Other domains like www.cnn.com resolve fine, so it’s not a general DNS issue.

What I’ve Tried:

  1. Double-Checked the Wildcard Record:
    • It’s set up correctly and points to the right IP.
    • No conflicting records exist.
  2. Client-Side Fixes:
    • I flushed the DNS cache.
    • Confirmed the client is pointing to the right DNS server (10.3.21.21).
    • Even tried adding wildcarduse.test.this.local to the hosts file, which worked, but that defeats the whole purpose of the wildcard.
  3. Testing the Network:
    • Connectivity to the DNS server is fine (ping 10.3.21.21 works).
    • Security groups in AWS allow DNS traffic (UDP/TCP on port 53) and ICMP.

My Questions:

  1. Is there something I’m missing with how wildcard DNS records work on Windows Server?
  2. Could this be related to AWS-specific settings like DHCP options or VPC configurations?
  3. Has anyone seen a similar issue and found a solution?

Details:

  • Both instances are in the same subnet, and DNS resolution for other domains works fine.

I’ve gone through all the usual troubleshooting steps, but I’m stuck. If you’ve got any ideas or suggestions, I’d really appreciate the help!

Thanks in advance! 😊