I have Xubuntu 14.04 on a SSD device (the HOME was encrypted correctly during intallation), additionally I have a HDD with a encrypted partition with extra data which I would like to mount in /mnt/hdd. For making these I followed the next steps:

(Previously I had encrypted the disk with LUKS following this post http://www.marclewis.com/2011/04/02/luks-encrypted-disks-under-ubuntu-1010/)

Check the UUID

sudo blkid 
/dev/sda1: UUID="b3024cc1-93d1-439f-80ce-1b1ceeafda1e" TYPE="crypto_LUKS"

Make a keyfile with the right passphrase and save it in my HOME (which is also encrypted).

sudo dd if=/dev/urandom of=/home/[USERNAME]/.keyfiles/key_luks bs=1024 count=4
sudo chmod 0400 .keyfiles/key_luks

Add the key

sudo cryptsetup luksAddKey /dev/sda1 /home/zeugor/.keyfiles/key_luks

New entry in /etc/crypttab

hddencrypted UUID=b3024cc1-93d1-439f-80ce-1b1ceeafda1e /home/[USERNAME]/.keyfiles/key_luks luks

Update the initial ramdisk

sudo update-initramfs -u -k all

Then, to test it, I used the follow command to start cryptdisks:

sudo cryptdisks_start hddencrypted 
 * Starting crypto disk... 
 * hddencrypted (starting)..
 * hddencrypted (started)...

To check hddencrypted was mapped:

ls /dev/mapper/
control hddencrypted

Create a mount point

mkdir /mnt/hdd

New entry in /etc/fstab

/dev/mapper/hddencrypted /mnt/hdd ext4 defaults 0 2

Validate fstab without reboot:

sudo systemctl daemon-reload
sudo mount -a

Mount the encrypted partition on boot

Now I have mount it in/mnt/hdd as I proposed. But I wold like to make this automatically after reboot. But before I can log in, I get this error:

the disk drive for /mnt/hdd is not ready yet or not permit

All this makes me think that /etc/crypttab can't access to the keyfile which is located in my HOME (other encrypted partition). I don't know the order which the system follows to unencrypted and mounts the units. My HOME should be unencrypted before my HDD for giving access to read the keyfile.

I would appreciate any insight as to why this happens.

UPDATE: If I locate the keyfile in /boot (no encrypted), instead of in my /home/[USERNAME] (encrypted) the /dev/sda1 and update the entry in /etc/crypttab is perfectly mounted on boot time.

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