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Excerpts from Byron McCollum's message of 2013-09-26 06:30:57 -0700:
> Are you talking about booting from a volume that was created from an image (bootable volume)?
> 
> Depending on cloud-init's configuration, it might be configured to only run on first boot. If that volume had previously been used to boot an instance, cloud-init will not run on subsequent boots from the volume.
> 

This is not true. cloud-init will run at every boot, and use the
meta-data it has access to to determine the current instance-id, and if
it has changed, cloud-init will run first-boot processes again such as
generating SSH keys and running cloud-config.

It sounds to me like cloud-init isn't even able to access the config
drive and thus can't determine the instance-id.

I wonder if the boot-from-volume has changed something about the
devices, and thus is getting in the way of how cloud-init discovers
the config-drive.

Your best bet is the console log, which will be where cloud-init prints
out what it is doing.