Hi Simon, I have the exact same problem. I gave up and decided to use ubuntu just yesterday after weeks of trying to figure it out. In my case when I try to bring up the VM by cloning a Debian template in proxmox with Terraform I get an error that sshd failed because it can't read hostkeys. So there seems to be a race initially between sshd and cloud-init even though the systemd files seem to be ok (sshd wants and after cloud-init). On another note, as you can read from the serverfault link below there is something wrong with the static vs dhcp configuration. Quoting from the article ``` Well after some digging it turns out the /etc/network/interfaces file, in addition to sourcing source-directory /etc/network/interfaces.d it also sources the extra directory /run/network/interfaces.d/. To my surprise, that /run directory contains an interface definition for ens3 where it is being configured in dhcp mode! ``` This creates a separate conflict where cloud-init is trying to set a static ip but there is still a file that says that it should be dhcp ip which could potentially be the cause of the first issue. I tried playing with the fai image generation that the debian cloud image team are using in order to generate their images but I gave up. https://serverfault.com/questions/1049250/debian-10-cloud-init-waiting-for-dhcp-on-boot-with-static-network-configuration
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