This seems to be an inotify issue - initctl isn't being notified of the new configuration. If I run:
$ initctl reload-configuration ...then everything works as expected. ** Package changed: openssh (Ubuntu) => linux-meta (Ubuntu) -- You received this bug notification because you are a member of Ubuntu Bugs, which is subscribed to Ubuntu. https://bugs.launchpad.net/bugs/1015348 Title: openssh-server package does not start sshd on a live CD boot To manage notifications about this bug go to: https://bugs.launchpad.net/ubuntu/+source/linux-meta/+bug/1015348/+subscriptions -- ubuntu-bugs mailing list ubuntu-bugs@lists.ubuntu.com https://lists.ubuntu.com/mailman/listinfo/ubuntu-bugs