Hello Azrex,
I meant by testing connectivity between inside and dmz if you are able to reach the DMZ environment from your inside network for example ping/telnet/ssh so we know that connectivity is not an issue.
Please check or answer following things:
a) switchport your end host is connected is it in the right vlan?
b) Do you have an SVI configured for that VLAN on your core switch and is it configured for dhcp relay?
for example -
Int vlan 2
ip helper-address 202.100.1.3
But I am not sure how your network looks like. Let us know if you are using your firewall inside interface as the default gateway for the client or is there a multilayer core switch on the inside network that client is using for default gateway. Can you draw your network and share it? Also is it just one client that's not getting address from the DHCP server or is it all the end hosts connected to inside network having the same issue?
The other thing you can do is look at the firewalls logs and debug commands on the asa:
debug dhcprelay
So after you initiate the debug command on the ASA, reboot the PC you are working on and when it comes back up it will broadcast DHCPDISCOVER packet. So your job will be to look at the firewall and see if it's getting those packets and what is it doing with them. Logs and debugging on the asa will give you a lot of information. If you don't see anything on the ASA then problem might be something internal like between the switch and end host.
Let me know if you have any questions.
