I had need for a Windows installation to process some old Outlook mail archives. The archive is quite large, so instead of moving the archives to a VM on my laptop, I decided to create a Windows 10 VM on the Ubuntu 18.04 server where the archives reside. I wanted to try to install the machine headless to VirtualBox and setup Guacamole to access it over a web server. This is the first time I have installed an OS that require a GUI installation process to VirtualBox without having direct access to the VirtualBox GUI.

Preparing the VM

I start by installing VirtualBox. We also need the VirtualBox Extension Pack to enable RDP access. And finally we need the VirtualBox Guest Additions ISO.

apt-get install virtualbox virtualbox-ext-pack virtualbox-guest-additions-iso

We create a VM definition with a name and an ostype. We also register it with VirtualBox right away.

VBoxManage createvm \
--name "Windows 10 mail" \
--ostype Windows10_64 \

We then set all the settings for the VM. Please refer to the VirtualBox manual to get a complete description of all the settings. Remember to update the ‘–memory’ and ‘–cpus’. Some especially interesting settings here are the network setup: ‘–nic1 bridge’ and ‘–bridgeadapter1 eno1’ adds a bridged network to the hosts network adapter ‘eno1’. You’ll likely need to change that to the correct name for your network adapter. (Try running ‘ip addr’ to get a list of all network adapters.)

VBoxManage modifyvm "Windows 10 mail" \
--memory 16384 \
--cpus 4 \
--acpi on \
--pae on \
--hwvirtex on \
--nestedpaging on \
--boot1 dvd \
--boot2 disk \
--nic1 bridged \
--bridgeadapter1 eno1

To access the VMs over RDP, we also enable the VirtualBox Remote Desktop Extension with ‘–vrde on’. It needs some authentication backend. We use ‘VBoxAuthSimple’. It is enabled with ‘–vrdeauthtype external –vrdeauthlibrary VBoxAuthSimple’. ‘VBoxAuthSimple’ allow us to write RDP usernames and password hashes to the ‘extradata’ section of each VM instead of relying on an external service. See the RDP Authentication section of the VirtualBox manual for an in-depth explanation.

VBoxManage modifyvm "Windows 10 mail" \
--vrde on \
--vrdeauthtype external \
--vrdeauthlibrary VBoxAuthSimple

To generate a hash of the password, run the following, where you substitute ‘secret’ with a proper password. I generate a random password with ‘pwgen’. Save the password for later. It needs to be entered in the Guacamole GUI. Tip you’ll properly want to prefix the following two commands with a space to prevent them from being saved to you bash history.

VBoxManage internalcommands passwordhash "secret"

Take the output from the above command and replace the hash below. It will write a key-value pair in ‘extradata’ of the username ‘guacamole-service-account’ and password for ‘VBoxAuthSimple’ to read.

VBoxManage setextradata "Windows 10 mail" "VBoxAuthSimple/users/guacamole-service-account" \

Create a storage controller, a virtual system disk and add the disk to the controller. Remember to change the path and maybe adjust the size.

VBoxManage storagectl "Windows 10 mail" \
--name "SATA" \
--add sata
VBoxManage createhd \
--filename /my/path/windows-10-mail.vdi \
--size 200000
VBoxManage storageattach "Windows 10 mail" \
--storagectl "SATA" \
--port 0 \
--device 0 \
--type hdd \
--medium /my/path/windows-10-mail.vdi

Download the Windows iso from Microsoft and place it somewhere on the host. Attach it to the VM with the following.

VBoxManage storageattach "Windows 10 mail" \
--storagectl "SATA" \
--port 1 \
--device 0 \
--type dvddrive \
--medium /my/path/Win10_1909_EnglishInternational_x64.iso

Also attach the VirtualBox Guest Additions ISO.

VBoxManage storageattach "Windows 10 mail" \
--storagectl "SATA" \
--port 2 \
--device 0 \
--type dvddrive \
--medium /usr/share/virtualbox/VBoxGuestAdditions.iso

If you are not already doing so, you’ll properly want to use ‘screen’ or ‘tmux’ for the next part as the command keeps running in the foreground and you don’t want it to exit if you lose your ‘ssh’ connection.

Start the VM in the foreground, so we can see the output:

VBoxHeadless --startvm "Windows 10 mail"

If you see ‘VRDE server is listening on port 3389.’ in the output, it works as expected.

Installing Guacamole

I run Guacamole in Docker. Refer to the Docker documentation for an installation instruction.

Due to the GUACAMOLE-962 bug in ‘1.1.0’. I run version ‘1.0.0’. It should be fixed in the upcoming ‘1.2.0’ release.

Create a ‘docker-compose.yml’ file somewhere on your system containing the following:

version: '3'

image: guacamole/guacd:1.0.0
restart: unless-stopped

image: postgres:12
- guacamole-db.env
restart: unless-stopped
- ./10-init.sql:/docker-entrypoint-initdb.d/10-init.sql:ro
- guacamole-db:/var/lib/postgresql/data:rw

image: guacamole/guacamole:1.0.0
GUACD_HOSTNAME: guacamole-guacd
- guacamole-db.env
- guacamole-guacd
- guacamole-db
# ports:
# - 8080:8080
restart: unless-stopped


Unfortunately, the official Guacamole docker images does not support Guacamoles default authentication. We are forced to use a database as the authentication backend. I use the PostgreSQL authentication. To connect the application to the database make a ‘guacamole-db.env’ file with the following content. You should update the password to something unique. Use ‘pwgen’ again.


‘POSTGRES_{USER,PASSWORD,DATABASE}’ is used by the guacamole docker image. ‘POSTGRES_{USER,PASSWORD,DB}’ is used by the postgres docker image. Beware that the role defined in ‘POSTGRES_USER’ created by the postgres docker image gets the ‘SUPERUSER’ role attribute. This is a potential security issue. The proper way to do it is to create a non-‘SUPERUSER’ role and grant it the privileges it needs.

The initialization of the database tables is a bit cumbersome. Unfortunately, the Guacamole docker image does not do it by itself. You need to run the following to get a script.

docker run --rm guacamole/guacamole:1.0.0 /opt/guacamole/bin/initdb.sh --postgres > 10-initdb.sql

This script can then be mounted into the ‘postgres’ container.

You’ll likely want this behind a reverse proxy. Refer to the Proxying Guacamole section in the Guacamole documentation. I use Traefik. You can also uncomment ‘ports: - 8080:8080’ in ‘docker-compose.yml’ to bind it to port 8080 of the host.

When you have the parts in place, you can run

docker-compose up -d

to start the services.

You should not be able to reach Guacamole at ‘http::8080/guacamole' (depending on your reverse proxy setup) and login with 'guacadmin:guacadmin'. See [Verifying the Guacamole install(https://guacamole.apache.org/doc/gug/guacamole-docker.html#verifying-guacamole-docker).

You should then change the password.

Connecting Guacamole to VirtualBox

In the Guacamole web UI, navigate to ‘Settings’ -> ‘Connections’ and press the ‘New connection’-button. Add a name like “Windows 10 mail VirtualBox”. Change the protocol to ‘RDP’.

Fill out the following fields under ‘PARAMETERS’:

  • Network
  • Hostname: the IP-address of your host machine where VirtualBox runs in the ‘Hostname’-field. (You cannot put ‘localhost’ here as it refers to the ‘guacd’-container.)
  • Port: ‘3389’
  • Authentication
  • Username: ‘guacamole-service-account’
  • Password: The password you put into ‘VBoxManage internalcommands passwordhash’ above.

Save the connection. Return to the Guacamole home screen and press the new connection. The Windows installation should now appear on the screen.

Install Windows

Complete the Windows installation. In this stage my mouse was not aligned properly. You can use the keyboard or just keep an eye on the “Windows mouse”.

When you are done with the installation, open the disk drive containing the VirtualBox Guest Additions. Install it and reboot. The mouse should now align properly.

Optional: Connecting Guacamole to Windows directly

While using the RDP from VitualBox works, you’ll have a better experience by connecting from Guacamole to the Windows RDP server directly. The Windows RDP server is only in Windows 10 Pro, not in Windows 10 Home.

First make sure the user account have a password set. Second you’ll properly want to make sure the Windows VM have a static IP-address.

Third go to Settings->System->Remote Desktop and Enable Remote Desktop.

In Guacamole add a second connection. Add a name like “Windows 10 mail Windows”. Change the protocol to ‘RDP’.

Fill out the following fields under ‘PARAMETERS’:

  • Network
  • Hostname: the IP-address of the Windows VM
  • Port: ‘3389’
  • Authentication
  • Username: Name of your Windows account
  • Password: The password of your Windows account
  • Security mode: ‘NLA’
  • Ignore server certificate: Checked

Save the connection. Return to the Guacamole home screen and press the new connection. This connection should be faster and stretch to fill the whole window.

Clean up

Finally, there are some clean up needed.

Start by shutting down the Windows machine. The ‘VBoxHeadless’ should now exit in the terminal.

Remove the Windows install ISO and the VirtualBox Guest Additions ISO.

VBoxManage storageattach "Windows 10 mail" \
--storagectl "SATA" \
--port 1 \
--device 0 \
--medium none
VBoxManage storageattach "Windows 10 mail" \
--storagectl "SATA" \
--port 2 \
--device 0 \
--medium none

At last start the VM in the background this time:

VBoxManage startvm "Windows 10 mail" --type headless