In case of failure (wrong password) the dm-crypt scripts used to ask again for the password for n times. This feature has been removed, in case of a type the user cannot respecify the password. The former solution was much more convenient.
looks to me like the code still asks for it ... the gpg loop executes 3 times which means you get three chances your bug report however is missing information ... if you consult the bug filing documentation: http://www.gentoo.org/doc/en/bugzilla-howto.xml you'll see that you need to report: - emerge --info - the version of cryptsetup you are using