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Hello,

Cloudbase-Init can only enable automatic updates if you set in the config file, in the DEFAULT section, the enableautomaticupdates to True:

[DEFAULT]
enableautomaticupdates

The functionality is the same to the one presented here:
https://support.microsoft.com/en-us/help/875349/how-to-change-your-automatic-updates-settings-by-using-windows-securit

Windows updates are usually very disruptive and can break functionality or even make the system as a whole unstable, if not proper curated and tested beforehand. Although cloudbase-init does not implement this functionality, you can use LocalScriptsPlugin (and the 1003 exit code each time you are required to perform a reboot) with this project https://github.com/cloudbase/WindowsUpdateCLI to automatically install updates.

You can find an advanced usage of the WindowsUpdateCLI project here:
https://github.com/cloudbase/windows-openstack-imaging-tools/blob/experimental/UnattendResources/Logon.ps1#L118

Thank you,
Adrian Vladu