Thanks for this investigation! This issue has been discussed in multiple places, like here where a udev rule is recommended: https://github.com/systemd/systemd/issues/2891
I wonder if we could downgrade the "Requires=sys-subsystem-net-devices- XXX.device" to a "Wants=sys-subsystem-net-devices-XXX.device" and add an additional triggering condition on the sysfs path ("ConditionPathExists=|/sys/subsystem/net/devices/XXX"). AFAIU this way the wpa_supplicant unit should fail immediately, if the devices (& its sysfs path) is not there but start as soon as the dongle is plugged in. https://systemd.network/systemd.unit.html#Conditions%20and%20Asserts I guess this needs some experimentation to fully understand the side- effects. ** Bug watch added: github.com/systemd/systemd/issues #2891 https://github.com/systemd/systemd/issues/2891 ** Changed in: netplan.io (Ubuntu) Status: Confirmed => Triaged ** Changed in: netplan.io (Ubuntu) Importance: Undecided => High ** Tags added: jj-rls-incoming -- You received this bug notification because you are a member of Ubuntu Bugs, which is subscribed to Ubuntu. https://bugs.launchpad.net/bugs/1906646 Title: Timed out waiting for device /subsystem/net/devices/wlan0 To manage notifications about this bug go to: https://bugs.launchpad.net/netplan/+bug/1906646/+subscriptions -- ubuntu-bugs mailing list ubuntu-bugs@lists.ubuntu.com https://lists.ubuntu.com/mailman/listinfo/ubuntu-bugs