If you want the mounting of your /data partition to block starting gdm,
you will need to add the 'bootwait' option to it in /etc/fstab. By
design, mount points that are not part of the FHS will not block the
boot; this is the best compromise between blocking the boot indefinitely
and leaving devices unavailable when they come up too late. Please see
<http://www.ubuntu.com/getubuntu/releasenotes/910#Optional%20encrypted%20partitions%20must%20be%20marked%20bootwait%20in%20/etc/fstab>
for more information.
There is a separate problem, that we have no way to prompt the user for
passphrases on devices that become available after gdm has started; this
bug is being tracked in bug #445888.
** Changed in: cryptsetup (Ubuntu)
Status: Incomplete => Won't Fix
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/etc/init.d startup scripts are not run at boot if bad (or timed-out) non-root
volume password
https://bugs.launchpad.net/bugs/495714
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