Changing DHCP server on Network ramifications

So basically you want your client to send their hostname to your DNS server ?

This works great with Windows clients, but for Linux machines, I would go the other way around : set your clients to ask the DHCP server for an IP and a hostname. Using the "request host-name" option, dhclient asks the DHCP server to send a hostname along with the IP address, then sets the hostname of the VM.

Of course you'll need to prepare, in your DNS, a hostname for each IP address in the DHCP range.

This way you don't have the DNS cache / propagation delay problem, and you may have a central place with all the IP and hostnames - your DNS server.

I don't know wether your appliance's DHCP server supports sending hostnames - most does, but I think that's the easiest way for Linux clients.

Note: If you configured your DHCP server so that the same machine always get the same IP address (e.g. using mac address) then it will, obviously, always get the same hostname too. On some DHCP server, you can use directly hostname instead of IP address in the config files.

You haven't actually verified that the Windows Server machine is receiving the DHCPDISCOVER requests. I'd throw a sniffer on it (either Microsoft Network Monitor or Wireshark) and verify that the packets really are making it to the server computer.

Are you certain your Ethernet switch doesn't have any "fancy" DHCP-related functionality that might be getting in the way? Your disappearing DHCP packets that you describe toward the end of your posting make me wonder if the switch is "swallowing" them somehow.

Edit: Zow-- I'm a moron! Talk about not being able to read.

Here's a silly question: Is the server computer's NIC configured with an IP address inside the subnet that the DHCP scope encompasses? If not, you'll need a DHCP relay agent (which could be running on your router) to forward the request to the server because, even though it's receiving the request at layer 2, if the server doesn't have a NIC in the subnet with the scope (or if the request doesn't come from a relay agent in the subnet that corresponds to the scope) the server won't answer.

If they're just RFC1918 IP addresses, go ahead and edit your question to include the server computer's IP address and the DHCP scope metes and bounds.