Just uploaded a new version of cryptsetup that fixes the echo -e bug, and also stops cryptsetup-enable from double-prompting (invisibly) for the same disk. That won't fix the root problem here, but may make debugging easier.
After upgrading, can you edit /etc/init/cryptdisks-udev.conf to attach to the running plymouth process with strace, to see what it's doing when it should be writing prompts? I wonder if it's trying to load plugins from disk, and this is failing because it's in some sort of limbo between the initramfs and the root system.
Something like the following should work (N.B.: untested, may hang your system, and definitely will break if you have more than one disk in /etc/crypttab):
Just uploaded a new version of cryptsetup that fixes the echo -e bug, and also stops cryptsetup-enable from double-prompting (invisibly) for the same disk. That won't fix the root problem here, but may make debugging easier.
After upgrading, can you edit /etc/init/ cryptdisks- udev.conf to attach to the running plymouth process with strace, to see what it's doing when it should be writing prompts? I wonder if it's trying to load plugins from disk, and this is failing because it's in some sort of limbo between the initramfs and the root system.
Something like the following should work (N.B.: untested, may hang your system, and definitely will break if you have more than one disk in /etc/crypttab):
pre-start script plymouth- not-prompting -p $(pidof plymouthd) &)
(strace -ff -e file -s 256 -o /var/run/
end script
post-start script
killall strace
end script