I'm still having this issue, I think it might be that when systemd-
networkd.service starts the /run/systemd/system/netplan-wpa-xxx.service
not generated yet! so it only works after a reboot or manually start it.

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https://bugs.launchpad.net/bugs/1874377

Title:
  Netplan does not connect to Wireless after `sudo netplan apply` until
  reboot

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