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What is the best way to copy files to and from a Tails Virtual machine running under virtualbox? I tried sharing a folder from my Host OS (OSX) and also installing guest additions (this caused the VM to shut down).

I understand there are security implications but for my use case, I want to use tails to download files via tor and then transfer them elsewhere.

  • Why run Tails under Virtualbox? – user66 May 7 '14 at 10:45
  • as a quick and dirty way to run a tor browser when the OSX tor browser bundle has stopped working. – codecowboy May 7 '14 at 10:55
  • When does TBB stop working on OS X? – user66 May 7 '14 at 10:57
  • see my other question on this forum – codecowboy May 7 '14 at 11:25
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You have many options, what you choose may depend on your personal level of expertise.

Starting from solutions that require least expertise but may have drawbacks:

  • Assuming you have a working Internet connections, you can use Internet Cloud storage as intermediate storage. Note, I will not advocate emailing to yourself which is commonly done because that will quickly use up your allotted mail storage unnecessarily. Examples of recommended Cloud Storage:

    • Dropbox
    • Google Drive
    • Microsoft OneDrive (aka SkyDrive)
    • Ubuntu One

      There are many others...

      From Tails, simply login and upload the file(s).

      From your other machine, login and download.

  • Local Network Shares. Do you know how to setup a network share? I won't go into the specifics, but if you know how to setup a network share SMB, HTTP, FTP or other protocol, then you should be able to do a normal network transfer.

  • Remote login. If you are able to "see" the other machine, then you can login to a Linux system like Tails with SCP, telnet, SSH from another system (If you're on Windows, you'll likely be using PuTTY). If you prefer a graphical interface, you'll likely use VNC.

  • Shared Local Storage. If you are able to configure direct access to the Guest (not always possible or easy), then you have a variation on the first option but without network bandwidth restrictions. This is typically configured in the Guest Settings. Note if you are able to configure direct physical access, it usually means that the Host and other Guests are unable to use that device at the same time.

  • Guest Extensions and the Virtualbox Shared Folder. May also depend on what your Host OS is. Guest Extensions should be the same version and likely be installed from the Host Virtualbox installation's files. You first need to configure the Shared Folder on the Host in the Guest Settings, then you need to mount the share in your in your Guest. Requires intermediate to advanced understanding of Linux, preferably Debian.

HTH, TSU

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I use a external usb drive that I mount. The drive is also full-disk encrypted with truecrypt. Plug it in. Then enable it un the lists of usb devices in virtualbox window. Tails will then find it as usb device just as normal.

  • can you share how you mount this? – codecowboy May 7 '14 at 16:28
  • Plug it in. Then enable it un the lists of usb devices in virtualbox window. Tails will then find it as usb device just as normal. – Stig Atle Steffensen May 7 '14 at 16:30
  • @StigAtleSteffensen: It is better to expand your answer with your latest comment. This way it helps other people. – Jens Kubieziel May 7 '14 at 19:58
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if your VM NIC operate in nat mode, the comunication between your host are limited. but, your NIC operate in bridge mode, use security copy over ssl channel, like scp, rsync and for ms windows clientes, winscp per example.

  • The VM starts in bridge mode but cannot connect to tor – codecowboy May 25 '14 at 11:13
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You can use netcat (nc) to communicate with another machine (e.g. host), if it also has netcat installed. Netcat is pre-installed in Tails, and most Linux disributions, and available for Windows as part of Cygwin or MSys, or standalone.

First start the netcat in listen mode (on the non-Tails machine, e.g. VirtualBox host):

nc -l 7777 > some_file.zip

Then send the file from Tails:

nc 10.0.2.2 7777 < some_file.zip

Host OS in VirtualBox, when NAT is configured, usually has IP 10.0.2.2 so the commands should work as is. Don't forget to change some_file.zip.

One caveat: there will be no transfer progress displayed and when it's done, nothing will happen. So you might check the file after some time, to determine if it has completely copied or not.

  • This answer rocks. I've edited it a little to make nc work. – TranslucentCloud Jul 12 '16 at 10:41

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