I have the same issue with Jaunty.
Here is the script to try same password for next device.

You can patch the file in place, or copy the file to 
"/etc/initramfs-tools/scripts/local-top/" before to patch it: it will override 
the file in "/usr/share".
Then run "sudo update-initramfs -u".

--- /usr/share/initramfs-tools/scripts/local-top/cryptroot      2009-03-08 
06:48:33.000000000 +0100
+++ /etc/initramfs-tools/scripts/local-top/cryptroot    2009-03-23 
08:43:11.780028000 +0100
@@ -270,9 +270,18 @@
                        cryptkey="Unlocking the disk $cryptsource 
($crypttarget)\nEnter passphrase: "
                fi
 
+               if [ -n "$PASS" ]; then
+                       # Try to unlock with previous password
+                       message "Unlocking the disk $cryptsource ($crypttarget) 
using the same password"
+               else
+                       # Ask for password
+                       PASS=$(crypttarget="$crypttarget" 
cryptsource="$cryptsource" \
+                            $cryptkeyscript "$cryptkey")
+               fi
 
-               if ! crypttarget="$crypttarget" cryptsource="$cryptsource" \
-                    $cryptkeyscript "$cryptkey" | $cryptcreate --key-file=- ; 
then
+               if ! echo -n "$PASS" | $cryptcreate --key-file=- ; then
+                       # Clear the wrong password
+                       unset PASS
                        message "cryptsetup: cryptsetup failed, bad password or 
options?"
                        continue
                fi


** Attachment added: "patch-script-cryptroot.diff"
   http://launchpadlibrarian.net/24245514/patch-script-cryptroot.diff

-- 
Should try given password for next partition
https://bugs.launchpad.net/bugs/139057
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