I wonder about a setup where I can have a primary OS on my Laptop, but keep a second OS that is safe, anonymous, persistent and isolated (for sensivite data that may communicate with the outside world).

The idea is that I can use the second OS to use the internet anonymously and keep private data that I don't want linked with my person in case my primary OS becomes compromised.

A Virtual machine wouldn't do it because a compromised host would have access to it. So I am thinking a dual boot with something like Whonix as encrypted secondary OS would be the safest option.
In this scenario, there is still a risk of a compromised Whonix having access to the primary OS partition, but is mitigated by the inherent security (Inernet connection via VM).

Are there simpler solutions for maximum security to isolate sensitive private data from everyday computer use not involving dual boot? Is there any caveat in the use that could lead to cross-contamination?

  • What is wrong with the question? I know I ask 'Is there anything wrong with my thinking', but given that it is a specific question, it seems answerable to me, not a discussion question. I summarize the problem in the first paragraph, I don't have code that needs to be formatted, I tagged the best match I could find (whonix not being a tag), and it it definitely about information security. I'm at a loss as to why the downvote. – TNT Feb 17 '16 at 3:36
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    The question is a little all over the place and you don't really talk about what you want to protect yourself or your data from. You are also providing a lot of different things to do and asking if there is anything wrong with them. As it stands, it's very difficult to answer because we would have to dismantle a lot of your underlying assumptions. If you were to narrow down the question a little, it would be better. – schroeder Feb 17 '16 at 4:39
  • Ok, thanks for the comment. I tried again; I thought it was clear I meant safety from access by system compromisation like a hacker, not from dataloss; What other assumptions? I provided an example now, hope it helps. – TNT Feb 17 '16 at 4:59

There are already some projects developed that are targeting your goal of safety. You should look at my old post.

For Type-2 hypervisors, there is RoboLinux project which has an unique feature called Stealth VM. Stealth VM software installer that allows you to build a Windows 7 clone running in a secure Linux partition. The system is protected from malware, anything you download will be contained within the virtual machine and it is intended for people who must have a specific Windows program with the convenience of being able to restore the operating system as new in just two clicks.

There is Qubes OS which is developed on Linux and Xen as an example for Type-1 hypervisors. Qubes OS takes an approach called security by isolation, which in this context means keeping the things you do on your computer securely isolated in different VMs so that one VM getting compromised won’t affect the others. Unlike Type-2 hypervisors, it has a secure inter-VM file transfer system to handle sharing folders' risk. In theory, that organization is more secure than Type-2 virtualization according to developers.

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  • Yes, I am looking at Qubes at the moment, but won't get to try it until next month. It does seem like what I am looking for, and has a Whonix VM integrated since the last version. – TNT Mar 20 '16 at 10:50
  • I think you typo'ed Qubes OS to be an example for Type-2 hypervisor, which should be Type-1 ? – TNT Mar 23 '16 at 5:00
  • I changed the linked and that post; I think I had a clerical error. Thank you for your attention. – JackSparrow Mar 24 '16 at 19:27

Try a USB bootable instance of Tails: https://tails.boum.org/

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  • Tails doesn't work for me as it's amnesic, I don't want to reinstall programs each working session – TNT Feb 18 '16 at 5:43

The safest method to not cross contaminate between the 2 OS's would be to have each one on a different hard drive and swap drives.

This would take more time to change between drives as you would have to open your hard drive bay and swap them, but they would be very very little (I don't want to say zero though) change that the secure OS could access the other OS.

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A simple way to keep an OS isolated is to use something along the lines of Kali linux on a bootable USB drive. Nothing is ever stored on the hard drive of your machine. Other than the fact that Kali will use the host memory while operating (which always leaves the possibility of compromise to an extent) anything you do while running off the bootable USB will stay within the bootable and not "cross-contaminate". When installing Kali on the USB, you can encrypt the OS and the USB, keeping what you do while running off the bootable secure and Kali has a plethora of tools for keeping your internet browsing safe, secure and anonymous. Once you're done, simply pulling out the bootable USB and restarting the machine leads you back to running the host OS (provided you set your BIOS to start from USB first, then the host hard drive secondary).

Hope this helps you in what you're looking for!

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  • Thanks, Kali looks like an alternative to Whonix; but doesn't keep your browsing in a virtual machine, does it? the USB option is nice I guess for portability but introduces the danger of your USB stick getting lost. I guess it is simpler though, as you don't have to configure dual booting and/or harddisc partitioning. – TNT Feb 18 '16 at 5:47
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    Kali is designed for Penetration testing. It is not safe to use as an anonymous, secureos for many reasons, including the fact that Kali is by default set up to run everything as root. Also, if an attacker gains access to your Kali instance, they can use the already installed penetration testing apps against your system and/or home network. – 16b7195abb140a3929bbc322d1c6f1 Feb 18 '16 at 6:05
  • Good point, back to Whonix, but on USB it is I guess, in that sense Kali makes cross-contamination easier by giving an attacker mount-rights if he gets into the Kali. Also made me think of one more step, to disable my usual HDD in BIOS if possible: howto. I'll check if my bios supports it. – TNT Feb 22 '16 at 3:06

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