I have Setup the cloud-init as the customization engine, based on this KB [2] instead which is similar to above mentioned KB [1] but it with two extra steps Item 3 and 4. i also made sure i have removed the After=Dbus.service
[2] https://kb.vmware.com/s/article/54986 The result is i see Customization event happening and successful in the VM Event ( so the VM still rebooted, is that Expected even though we configured cloud-init to be the customization engine? ), Network connected, Static IP provided and hostname updated but none of the userdata Cloud config made it through like for example installing mysql-server package. at this point i m confident there is no solution here for cloud-init to work on VMware unless someone else tells me otherwise. i will be more focused on introducing Ansible open source to deliver packages , etc and remove cloud-init completely from the template -- You received this bug notification because you are a member of Ubuntu Bugs, which is subscribed to Ubuntu. https://bugs.launchpad.net/bugs/1833623 Title: VMware Guest OS Customization Fail for Ubuntu 16.04 with Cloud-init 19.1 To manage notifications about this bug go to: https://bugs.launchpad.net/ubuntu/+source/cloud-init/+bug/1833623/+subscriptions -- ubuntu-bugs mailing list ubuntu-bugs@lists.ubuntu.com https://lists.ubuntu.com/mailman/listinfo/ubuntu-bugs