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Firstly, if you used the cloudbase-init installer with the sysprep part, the password for the Administrator password is being reset. If you have set Administrator as the default username, its password will be randomly generated by cloudbase-init or taken from the metadata service.

Secondly, there is a delay between the boot process finish and the actual plugin execution, which leads to the behavior you are getting, as the cloudbase-init process takes some time to retrieve the metadata providers. In a cloud scenario, the user does not have access to the vm's console, thus will be unable to connect to that vm until cloudbase-init finishes the createuser and setuserpassword plugins. For example, if you are using OpenStack with http metadata service, the user can retrieve the password using "nova get-password" and use the default username to connect to that Windows vm.