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The current implementation of handleCloudInitNotStarted() does some checks to guess if cloud-init was successfully or not.
We could improve that by added a touch /root/preKubeadmCommand-success-HBMM_MACHINEUUID
and touch /root/postKubeadmCommand-success-HBMM_MACHINEUUID at the end of the pre/post Kubeadm commands.
If these files do not exist, then something went wrong.