We have some similar problem on bug #83231. I proposed them your solution based on udevsettle, and it works. I also tried to add the "udevsettle --timeout XX" at the end of /usr/share/initramfs-tools/scripts/init-premount/udev.
May someone using cryptoroot try this ? if it works for you too, we have a global solution for both bugs. -- [Feisty] crypted root doesnt mount on start (cryptsetup) https://launchpad.net/bugs/85640 -- ubuntu-bugs mailing list ubuntu-bugs@lists.ubuntu.com https://lists.ubuntu.com/mailman/listinfo/ubuntu-bugs