This looks very similar to bug 296464 to me. the extra prompt at boot time is likely just a prompt for the crypted swap partition.
There is a patch to mkinitrd attached to that bug [0] which avoids
running cryptsetup on devices with a key specified in /etc/cryptab
during the initrd phase.
hth,
--dkg
[0] http://bugs.debian.org/cgi-bin/bugreport.cgi?bug=296464
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