Source
r/tails•
etcNetcat

Issues using Tails with VirtualBox

Installation issues

I am running Windows 10.

I am trying to use the latest Tails image with a fresh install of VirtualBox. However, two issues present themselves when following the instructions for running from a VM.

  1. VirtualBox does not see the .img as being a valid disk image.

This can be solved, says google, by renaming it to an .iso: I am not sure if that is sufficient, but I gave it a try. If that is sufficient, I have a second problem:

  1. Despite following every step of that guide and triple-checking, and then renaming it to an ISO in desperation, I get the error "could not read from the boot medium" before Tails even gets a chance to appear.

I have been looking around and I searched this subreddit using the keyword "virtualbox" and didn't find anything helpful. The VM is definitely on IDE mode and not SATA. My thought is that perhaps I need to somehow truly convert it from an IMG to an ISO, but I thought I should ask here for recommendations before I flail around in the dark anymore.

I am using a VM for a reason, please don't go off about how I shouldn't use the VM because of the security issues.

Posted May 14, 2022, 4:32 AM UTC

210
klenha•

why not whonix though

3
etcNetcatOP•

I'm investigating the feel of several different OSes, actually, which is why I'm spinning them up in virtualbox. Whonix is on the list.

1
klenha•

i see.

1
Multicorn76•

Virtually all of them are based on Linux. You can customize every last line of code in linux, so just take the safest (whonix if you are using linux as host os) and customize the gui. Wouldn't recommend touching the security configurations whonix has, but when you are talking about "feel" your mistake is choosing the one with the prettiest desktop, and not necessarily the most secure for your usecase

1
etcNetcatOP•

actually honestly leaning towards avoiding pretty desktops, prefer fewer animations and less gloss

2
Multicorn76•

Its all tweakable, you just gotta know how, which can be a problem.

1
doogusto•

Every time I torrent tails it downloads as an iso. You might be clicking the wrong link on the site. There is no way to convert an img to iso since both are compiled binaries.

You could try flashing it to a virtual disk from inside your vm if nothing else

1
etcNetcatOP•

I'll try torrenting it, thanks. Maybe that's the key.

EDIT: I didn't click on "make a DVD", that's where the ISO is. Why can't they just have a list of file types?

0
Liquid_Hate_Train•

Because it’s a set of instructions which it’s expected you are following, so it gives you the file appropriate for those instructions.

I also hope you read all the security implications of running in a VM and understand that Tails is substantially weakened by doing so.

1
etcNetcatOP•

As I said in the main post, I'm aware of the security implications. I'm investigating the feel of several different OSes, actually, which is why I'm spinning them up in virtualbox. Once I sus out which one I like the most, I'll implement it fully in a hardened configuration.

1