@Dan, The issue is resolved by your fix.

Instead of only changing /etc/dhcp/dhclient-enter-hooks.d/resolved
script, I added your repository "ppa:ddstreet/systemd" and
updated/upgraded systemd, then the issue was NOT reproducing.

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https://bugs.launchpad.net/bugs/1850775

Title:
  DNS info is not loaded by dhclient

Status in network-manager package in Ubuntu:
  Confirmed
Status in systemd package in Ubuntu:
  New

Bug description:
  Hi Team,

  Could you please help to confirm if this is an issue on Ubuntu19.10
  Desktop?

  1. Update /etc/dhcp/dhclient.conf file to include below 2 new lines.
     supersede domain-name "vmware.com";
     supersede domain-name-servers 10.117.0.1;

  2. Reboot

  3. check DNS info by "systemd-resolve --status", the DNS domain and
  server is not set. But /run/systemd/resolved.conf.d/isc-
  dhcp-v4-ens160.conf contains the new DNS domain and server.

  4. Manually run "systemctl try-reload-or-restart systemd-
  resolved.service" and then DNS is set correctly, "systemd-resolve
  --status" output have the new DNS domain and server.

  
  I tried the same steps on Ubuntu18.04 Desktop, no such issue. DNS updated 
correctly after reboot.

  Thanks,
  Pengpeng

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