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I recently tried tails and I find it pretty interesting but I am having troubles creating a windows VM inside it.

My idea was to install virtualbox automatically on boot using the persistance feature and save my vm disk on the persistant folder then open that machine and have my work saved.

I install vbox using sudo apt-get install virtualbox-qt (dont know why I have to use -qt) then initiate vbox with virtualbox and it starts but some warning does appear which says something like

the character device /dev/vboxdrv does not exist. Please install the virtualbox-dkms package and the appropiate headers...

I googled "virtualbox linux problems" because I figured this would be a general linux related issue, not something that has necessarely to do with tails and I got here:

https://askubuntu.com/questions/41118/virtualbox-kernel-driver-not-installed

I tried most suggested fixes which seemed to work for some people but couldn't get it to work because some files/folders didn't exist. I am pretty noob with linux so I can't figure this out alone.

I would really appreciate any helpful feedback, thanks.

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I would strongly recommend against this. Infact other software that requires dkms modules is explicitly recommended against by the Tails developers. It is not officially supported by them. Inserting random code into the kernel may entirely violate protections intended to be provided by Tails.

I'm unsure if it is possible to include extra kernel drivers without including them at build time, you would likely need to build your own custom Tails ISO. The reason being that any packages (e.g. the vbox kernel modules that are built) would not be stored.

You may be able to build the dkms package and then use modprobe to load the module but expect problems:

  1. If your guest operating system has pass-through access to hardware devices, it might violate anonymity. (It can read hardware IDs and send them out to the internet).
  2. Within it's own persistent vbox disk it will still be writing a lot of data about what it's doing to disk, it will be storing long term meta-data about your activities.
  3. You will have problems accessing the internet due to Tails' strict iptables rule-set, it will not automagically send the guests traffic through Tor, VirtualBox would need to be configured to use one of the provided SOCKS ports.
  4. This will require root access for every boot of Tails, allowing the amnesia user the ability to escalate to root should be avoided where possible since root has the ability to permanently alter or infect the Tails USB.
  5. Everything on Tails is in RAM and virtual machines are notoriously greedy with RAM, you will be severely restircted in the RAM available.
  6. It's Oracle software.
  7. It's Windows running on Oracle software.

You will need to enable the contrib debian repo for jessie, install the appropriate linux headers (possibly from jessie-backports, as that's where the Tails kernel is pulled from) and then run apt-get update then apt-get install virtualbox. According to the Debian documentation this show allow the proprietary software to be included which is required to build VirtualBox. These steps will need to be performed every time you boot Tails.

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