The DHCP User Experience Monitor functions no differently than a workstation configured to use DHCP. That is to say, we are bound by the same RFC limitations as any other DHCP client. Unfortunately, requesting DHCP leases for a network segment other than the one you're on simply not allowed by the DHCP RFC. The only workaround I can think of off the top of my head is placing an Additional Poller on that network segment, though that's probably overkill in your scenario. To be honest though it's probably unnecessary too as if you're able to obtain a DHCP lease from that DHCP server then your DHCP server is working and granting leases. The only reason why it would work for one subnet and not another is if the DHCP server was out of leases in a particular scope. To monitor for that condition I recommend using the "Windows DHCP Server" or "ISC DHCP Server (Linux)" templates. Better yet, you might want to consider looking at IP Address Manager.
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