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Hello,

this looks like a bug in cloudbase-init that needs further investigation. A similar resolution like this one from Ansible might fix this issue though. reboot -> if shutdown in progress -> abort shutdown -> go to reboot.

Practically, if we add here a verification if a shutdown is already in progress and we abort it, it might solve this issue: https://github.com/cloudbase/cloudbase-init/blob/f8479e5cbc27c88f4fcf9a781d7cd5d6b7a9ff74/cloudbaseinit/osutils/windows.py#L429 . The method to be used would be https://docs.microsoft.com/en-us/windows/win32/api/winreg/nf-winreg-abortsystemshutdownw .

Thank you.