Recently, I’ve implemented full-disk encryption on every machine at the lab.

For the 30 or so Linux boxes, this meant setting up LUKS. We’re a Ubuntu shop here, so that meant following the instructions here. Actual setup of encryption is outside of the scope of this document. I may write an article on it at some point in the future.

Having set up encryption, when the system boots the user is prompted to enter a password at the console. Given the amount of time I spend working from remote, this is a problem. I can’t reboot any boxes without being on-site, and any wild power events or reboots render all 30 of our servers unusable until they’re manually reset.

What I outline here is the first step in a solution. The second step will come in a later article and explain how to mass-automate the startups. This article covers setting up dropbear so that you can use SSH to log into your system at boot time and unlock the system from remote. There are probably a host of other uses for this hack – remote wiping of the drives is the first thing that springs to mind.

There are a few guides out there for this, but none of them work (because of improper dropbear configuration). That said, I found useful information at the following places:

Anyway, without further ado, here’s how to set up your Ubuntu Server 17 boxes for remote LUKS unlock. I used nano here, but you can use any text editor of your choice.

Step 1. Install dropbear and busybox

sudo apt-get install dropbear busybox

You will get a warning here as it completes: “dropbear: WARNING: Invalid authorized_keys file, remote unlocking of cryptroot via SSH won’t work!” – ignore it.

Step 2. Activate BUSYBOX and DROPBEAR in initramfs

sudo nano /etc/initramfs-tools/initramfs.conf

Set the “BUSYBOX” option to “y” and add a line below it that says “DROPBEAR=y”

Step 3. Generate our keys, convert the openssh key to dropbear format, and copy all of the files into /etc/dropbear-initramfs where they belong.

dropbearkey -t dss -f dropbear_dss_host_key
dropbearkey -t rsa -f dropbear_rsa_host_key
dropbearkey -t rsa -f id_rsa.dropbear
/usr/lib/dropbear/dropbearconvert dropbear openssh id_rsa.dropbear id_rsa
dropbearkey -y -f id_rsa.dropbear |grep "^ssh-rsa " >
touch authorized_keys
cat >> authorized_keys
sudo cp dropbear_* /etc/dropbear-initramfs/
sudo cp id_* /etc/dropbear-initramfs/
sudo cp authorized_keys /etc/dropbear-initramfs/

Note, if you don’t HAVE a /etc/dropbear-initramfs folder, do the following:

sudo mkdir /etc/initramfs-tools/root
sudo mkdir /etc/initramfs-tools/root/.ssh
sudo cp dropbear_* /etc/initramfs-tools/root/.ssh/
sudo cp id_* /etc/initramfs-tools/root/.ssh/
sudo cp authorized_keys /etc/initramfs-tools/root/.ssh/

Step 4. Set dropbear to start

sudo nano /etc/default/dropbear

Change NO_START=1 to NO_START=0

Step 5. install the crypt_unlock script

sudo nano /etc/initramfs-tools/hooks/
sudo chmod +x /etc/initramfs-tools/hooks/



prereqs() {
  echo "$PREREQ"

case "$1" in
    exit 0

. "${CONFDIR}/initramfs.conf"
. /usr/share/initramfs-tools/hook-functions

if [ "${DROPBEAR}" != "n" ] && [ -r "/etc/crypttab" ] ; then
cat > "${DESTDIR}/bin/unlock" << EOF
if PATH=/lib/unlock:/bin:/sbin /scripts/local-top/cryptroot; then
kill \`ps | grep cryptroot | grep -v "grep" | awk '{print \$1}'\`
# following line kill the remote shell right after the passphrase has
# been entered.
kill -9 \`ps | grep "\-sh" | grep -v "grep" | awk '{print \$1}'\`
exit 0
exit 1
  chmod 755 "${DESTDIR}/bin/unlock"
  mkdir -p "${DESTDIR}/lib/unlock"
cat > "${DESTDIR}/lib/unlock/plymouth" << EOF
[ "\$1" == "--ping" ] && exit 1
/bin/plymouth "\$@"
  chmod 755 "${DESTDIR}/lib/unlock/plymouth"
  echo To unlock root-partition run "unlock" >> ${DESTDIR}/etc/motd

I found this script here. I’ve inlined it on this page in case the original goes away.

Step 6. Update initramfs with the changes

sudo update-initramfs -u

Step 7. Disable dropbear on your booted system.

sudo update-rc.d dropbear disable

Step 8. Download and convert the key for use with putty
Download the id_rsa file you created above. You’ll need to convert it from RSA to a putty key.
Import it in puttygen.exe (Conversions/Import Key)
Save the private key.

Step 9. Create a putty session
Open putty as you normally would.
Set Connection/Data/Auto-login username to “root”.
On the Connection/SSH/Auth screen, browse and load the private key you saved, using the “Browse…” button on the “Authentication parameters” panel.
Save this session.

How to unlock your system (finally)
Finally, you should be able to connect to your rebooted (and awaiting unlock) server. Open putty, load your session, and connect.
If you’ve done everything properly, you’ll get a prompt.
At the prompt, use the command “unlock”.
If you’ve entered the proper password, your server will reboot and dropbear will disconnect. Wait a bit for it to complete booting and you should be able to log in as normal.