On my network I have two subnets: 10.100.1.0/24 - Wired/wireless 10.100.7.0/24 - VPN Both subnets are served by isc-dhcp-server running on a Debian VM. This same VM runs bind9 for my DNS. ISC-DHCP-SERVER is configured to use DDNS and update BIND9 with hosts/IPs. Everything runs great until a device drops off the wired/wireless network and pops onto the VPN. When connecting on the VPN, a DHCP lease is handed out on the new subnet but DDNS does not update BIND9. Since the device has A/TXT/PTR records it appears ISC-DHCP-SERVER won't switch them to the new IP. The logs show: Connect to wireless: Nov 6 20:55:13 core-server named[2417]: client 127.0.0.1#57697: updating zone 'internal.mydomain.com/IN': adding an RR at 'demo-iphone.internal.mydomain.com' A Nov 6 20:55:13 core-server named[2417]: client 127.0.0.1#57697: updating zone 'internal.mydomain.com/IN': adding an RR at 'demo-iphone.internal.mydomain.com' TXT Nov 6 20:55:13 core-server dhcpd: DHCPACK on 10.100.1.160 to FF:FF:FF:FF:FF:FF (demo-iphone) via eth0 Nov 6 20:55:13 core-server dhcpd: Added new forward map from demo-iphone.internal.mydomain.com to 10.100.1.160 Nov 6 20:55:13 core-server dhcpd: Added reverse map from 160.49.21.172.in-addr.arpa. to demo-iphone.internal.mydomain.com Switch to VPN: Nov 6 20:56:34 core-server dhcpd: DHCPOFFER on 10.100.7.101 to BB:BB:BB:BB:BB:BB (demo-iphone) via 10.100.7.0 Nov 6 20:56:34 core-server named[2417]: client 127.0.0.1#57697: updating zone 'internal.mydomain.com/IN': update unsuccessful: demo-iphone.internal.mydomain.com: 'name not in use' prerequisite not satisfied (YXDOMAIN) Nov 6 20:56:34 core-server dhcpd: DHCPREQUEST for 10.100.7.101 (10.100.1.2) from BB:BB:BB:BB:BB:BB (demo-iphone) via 10.100.7.0 Nov 6 20:56:34 core-server dhcpd: DHCPACK on 10.100.7.101 to BB:BB:BB:BB:BB:BB (demo-iphone) via 10.100.7.0 Nov 6 20:56:34 core-server named[2417]: client 127.0.0.1#57697: updating zone 'internal.mydomain.com/IN': update unsuccessful: demo-iphone.internal.mydomain.com/TXT: 'RRset exists (value dependent)' prerequisite not satisfied (NXRRSET) Nov 6 20:56:34 core-server dhcpd: Forward map from demo-iphone.internal.mydomain.com to 10.100.7.101 FAILED: Has an address record but no DHCID, not mine. One thing to note is that the MAC of the device when connecting via VPN is the MAC of my Cisco ASA5512X and not the actual device. The ASA is relaying the DHCP request from the VPN client to the VM running ISC-DHCP-SERVER. Is there a way to get DDNS working in this scenario?