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In this case, I suggest you to use a configuration management tool like Chef, Puppet or Ansible. The main responsibility of Cloudbase-init (or cloud-init) is to provision the instance at the first boot time, and not to configure it during its lifecycle. In OpenStack there is no option to reset the password of the machine, thus it cannot be implemented by cloudbase-init.

A workaround in your case would be to rescue the Windows instance and from rescue mode change the configuration appropriately (there are various methods to change the Windows password from a rescue OS).

Thank you,
Adrian Vladu