I have the same problems. First mount after reboot is OK. Subsequent
attempts either fail to popup the passphrase dialog or take the
passphrase but do not mount the drive.

In the case where the passphrase dialog did not appear, I attempted to
mount the volume by hand using

/usr/bin/gnome-mount --hal-
udi=/org/freedesktop/Hal/devices/volume_uuid_c52cc2c6_8fbd_41b3_a99f_f4a7d3132c9c

but this command did not pop up the passphrase dialog and exited with
status 1.

I then recompiled the gnome-mount package with
DEB_BUILD_OPTIONS=noopt,nostrip and installed it.  I repeated the same
gnome-mount command with the addition of the "-b" flag (to stop the
mount command from daemonizing).  Under gdb, I traced the problem this
far:

3077                         if (clear_udi != NULL) {
3078                                 g_warning (_("Crypto volume '%s' is 
already setup with clear volume '%s'"), 
3079                                          udi, clear_udi);


(gdb) print clear_udi
$3 = 0x659f10 
"/org/freedesktop/Hal/devices/volume_uuid_488bc1b0_3344_41aa_88b7_e6e1a36ee062"

So, in this case it thinks it already has constructed the clear text
volume? Perhaps HAL has some stale information in its cache from the
previous mount?

I'm away from my Ubuntu system at the moment so cannot give any more
information for a week or too.

-- 
mounting Luks encrypted USB-HDD does not work reliably
https://bugs.launchpad.net/bugs/148003
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