Deepika, Frank, is this happening for you inside an unprivileged
container, or some other environment?

I'm able to reproduce this in a container, but it appears still broken
with upstream systemd, so I'm confused by Frank's comment 2.  Also, it
isn't intermittent at all for me, so maybe you're seeing some other
problem.

** Changed in: systemd (Ubuntu)
       Status: Fix Released => Incomplete

** Changed in: systemd (Ubuntu Bionic)
       Status: New => Incomplete

** Changed in: systemd (Ubuntu Focal)
       Status: In Progress => Incomplete

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https://bugs.launchpad.net/bugs/1930738

Title:
  network configuration failed on reboot

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