dnsmasq server conf: domain=test,1.2.3.4/24 dhcp-range=test,1.2.3.100,1.2.3.199,1m dhcp-option=42,1.2.3.1 #dhcp-option=121,0.0.0.0/0,1.2.3.1 test system conf: ubuntu@lp1835581-e:~$ cat /etc/systemd/network/10-ens8.network [Match] Name=ens8 [Network] DHCP=ipv4 LinkLocalAddressing=ipv6 Address=1.2.3.99/24 ubuntu@lp1835581-e:~$ dpkg -l systemd|grep ii ii systemd 242-7ubuntu3 amd64 system and service manager ubuntu@lp1835581-e:~$ ip -4 a show ens8 3: ens8: mtu 1500 qdisc fq_codel state UP group default qlen 1000 inet 1.2.3.99/24 brd 1.2.3.255 scope global ens8 valid_lft forever preferred_lft forever inet 1.2.3.170/24 brd 1.2.3.255 scope global secondary dynamic ens8 valid_lft 98sec preferred_lft 98sec ubuntu@lp1835581-e:~$ ip -4 r default via 1.2.3.1 dev ens8 proto dhcp src 1.2.3.170 metric 1024 1.2.3.0/24 dev ens8 proto kernel scope link src 1.2.3.99 1.2.3.1 dev ens8 proto dhcp scope link src 1.2.3.170 metric 1024 route src is correctly set to dhcp addr, when dnsmasq not configured with classless route uncomment dnsmasq server conf classless route: domain=test,1.2.3.4/24 dhcp-range=test,1.2.3.100,1.2.3.199,1m dhcp-option=42,1.2.3.1 dhcp-option=121,0.0.0.0/0,1.2.3.1 reboot test system: ubuntu@lp1835581-e:~$ ip -4 a show ens8 3: ens8: mtu 1500 qdisc fq_codel state UP group default qlen 1000 inet 1.2.3.99/24 brd 1.2.3.255 scope global ens8 valid_lft forever preferred_lft forever inet 1.2.3.170/24 brd 1.2.3.255 scope global secondary dynamic ens8 valid_lft 110sec preferred_lft 110sec ubuntu@lp1835581-e:~$ ip -4 r default via 1.2.3.1 dev ens8 proto dhcp metric 1024 1.2.3.0/24 dev ens8 proto kernel scope link src 1.2.3.99 route src incorrectly not set, when dnsmasq set to classless route change dnsmasq server again to comment out classless route and restart it, then reboot test system: ubuntu@lp1835581-e:~$ dpkg -l systemd|grep ii ii systemd 242-7ubuntu3.2 amd64 system and service manager ubuntu@lp1835581-e:~$ ip -4 a show ens8 3: ens8: mtu 1500 qdisc fq_codel state UP group default qlen 1000 inet 1.2.3.99/24 brd 1.2.3.255 scope global ens8 valid_lft forever preferred_lft forever inet 1.2.3.170/24 brd 1.2.3.255 scope global secondary dynamic ens8 valid_lft 97sec preferred_lft 97sec ubuntu@lp1835581-e:~$ ip -4 r default via 1.2.3.1 dev ens8 proto dhcp src 1.2.3.170 metric 1024 1.2.3.0/24 dev ens8 proto kernel scope link src 1.2.3.99 1.2.3.1 dev ens8 proto dhcp scope link src 1.2.3.170 metric 1024 re-enable classless route on server and reboot test system: ubuntu@lp1835581-e:~$ ip -4 a show ens8 3: ens8: mtu 1500 qdisc fq_codel state UP group default qlen 1000 inet 1.2.3.99/24 brd 1.2.3.255 scope global ens8 valid_lft forever preferred_lft forever inet 1.2.3.170/24 brd 1.2.3.255 scope global secondary dynamic ens8 valid_lft 104sec preferred_lft 104sec ubuntu@lp1835581-e:~$ ip -4 r default via 1.2.3.1 dev ens8 proto dhcp src 1.2.3.170 metric 1024 1.2.3.0/24 dev ens8 proto kernel scope link src 1.2.3.99 route is correctly sourced from dhcp address