This issue doesn't reproduce on 22.04 Live server image, its '/usr/lib/systemd/system/systemd-networkd.socket' is same with 22.04 Desktop image, so looks like shutdown.target in systemd-networkd.socket is not the root cause. I think the systemd dependence is quite different between Desktop and Server images, please systemd experts look into this.
By running below command on Ubuntu 21.04 Desktop, Ubuntu 22.04 Desktop and Ubuntu 22.04 Server VMs, got some .svg files, attached them in svg_files.zip to this bug for your reference. 1. systemd-analyze plot > plot2104_desktop.svg 2. systemd-analyze plot > plot2204_desktop.svg 3. systemd-analyze plot > plot2204_server.svg 4. systemd-analyze dot 'systemd-networkd.service' | dot -Tsvg > dot2104_desktop.svg 5. systemd-analyze dot 'systemd-networkd.service' | dot -Tsvg > dot2204_desktop.svg 6. systemd-analyze dot 'systemd-networkd.service' | dot -Tsvg > dot2204_server.svg According to the plot output, systemd-networkd starts late only on Ubuntu 22.04 Desktop VM, this leads to customization command 'netplan apply' fail. ** Attachment added: "svg files" https://bugs.launchpad.net/ubuntu/+source/systemd/+bug/1962843/+attachment/5566877/+files/svg_files.zip -- You received this bug notification because you are a member of Ubuntu Bugs, which is subscribed to Ubuntu. https://bugs.launchpad.net/bugs/1962843 Title: Guest OS customization fail for ubuntu 22.04 desktop in vsphere due to adding 'shutdown.target' in file /usr/lib/systemd/system/systemd- networkd.socket To manage notifications about this bug go to: https://bugs.launchpad.net/ubuntu/+source/systemd/+bug/1962843/+subscriptions -- ubuntu-bugs mailing list ubuntu-bugs@lists.ubuntu.com https://lists.ubuntu.com/mailman/listinfo/ubuntu-bugs