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If you refer to the runcmd from cloud-config userdata, the state of that plugin is saved in the registry keys: HKLM:\\SOFTWARE\\Cloudbase Solutions\\Cloudbase-Init\\<INSTANCE-ID>\\<PLUGIN-NAME>

In your case, PLUGIN-NAME is UserDataPlugin. You need to remove that key or if you want to do a full rerun, just remove HKLM:\\SOFTWARE\\Cloudbase Solutions\\Cloudbase-Init\\.

Thank you,
Adrian Vladu