Tails is a privacy focused Live operating system

Martin Brinkmann
Sep 20, 2015

I have not covered Live operating systems in a long while. These systems are usually Linux-based and allow you to boot into the system without installing software or making any changes to the data that is on a computer.

Basically, they run independent of the host system they are run on which, as an added side-effect, means you can run them on nearly any computer system that supports USB, SD cards or optical discs.

Tails is a privacy-focused Live operating system that is easy to use but mighty powerful at the same time.

Preparing Tails

Probably the easiest way to create bootable media using Tails is to download the latest ISO image that is offered on the official site. You can use the direct download for that or download it via BitTorrent instead.

The team suggests you verify the ISO image after the download to make sure it is legitimate and has not been tampered with. Instructions on how to do that are provided on the website.

Once done, burn the ISO image directly to DVD or install it on a USB device or SD card. Instructions on how to do that are also provided on the website under First steps with Tails.

The main advantage of USB or SD is that you can create encrypted persistent storage to save data across sessions.

Using Tails

This is where it gets interesting. You may need to configure the boot order of the system to boot Tails and not the other operating systems that may be installed on computer's hard drives.

Once Tails starts up, you are walked through a short introductory sequence that already highlights some of the unique features of Tails.

Among the options there are to activate a camouflage option to make Tails look more like Windows 8, an option to spoof MAC addresses and initial network configuration options.

This may sound confusing but the options presented are easy to understand and don't require that you make any manual input at this point in time (apart from selecting an administrator password that is).

Tails should work automatically from that moment on in most cases. The system connects to TOR automatically to secure network traffic and the TOR browser is the main Internet browser. It is a modified version of Firefox with improved privacy and several add-ons such as NoScript or HTTPS Everywhere installed.

Tails ships with a truck load of nice to have features including LibreOffice, the instant messaging software Pidgin that is preconfigured with OTR (Off the Record Messaging), a feed reader, Bitcoin client, the mail program Claws Mail with GnuPGP support and a lot more. The full list of supported programs is provided on the official website.

You may run into issues however when using Tails due to security limitations. File uploads to the Internet are not permitted for instance, and if you connect another USB drive to the computer, you will notice that you cannot select it to save files on it.

Closing Words

Tails is a privacy powerhouse. It encrypts Internet connections using TOR so that you remain anonymous on the Internet and can bypass censorship or blocked resources. Files, emails and instant messaging ships with encryption turned on by default for extra security, and since it is a live environment, it won't leave any traces on the underlying system unless explicitly permitted by the user first.

Linux users will feel right at home for the most part while Windows users may have a harder time adjusting especially if something is not working out of the box.

A good place to start troubleshooting is the official website and there especially the getting started guide and documentation.

Tails is a privacy focused Live operating system
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Tails is a privacy focused Live operating system
Tails is a live operating system based on Linux that is been designed for maximum privacy and security on the Internet.

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  1. hirobo2 said on September 22, 2015 at 8:15 pm

    Scary stuff… The only ppl using Tails are the ppl that have something to hide, so the NSA is tracking ’em…

  2. jasray said on September 21, 2015 at 2:22 am

    The encrypted persistent storage mentioned is a bit different than some may expect. I found Tails to be an interesting tool, but TOR is compromised–NSA and all other security agencies–know exactly how it works, so forget the fiction that Tails is the stuff of spy movies.

    If one is online, one is compromised and leaving a trail. The best way to take care of whatever business needs to be taken care of is to stay off of computers. Try a “burner” phone and meet in person? That’s even traceable. Try a 9/11–learn to think like they thought. How can I use “the enemy of my enemy is my friend” motif to be invisible by being completely visible. 9/11, from a military strategist point of view, was brilliant.

    It’s a sad day that most don’t know about: MIA. If readers haven’t watched the ceremony performed, it may be on YouTube. If anyone has a lost brother or father or mother, KIA, MIA, POW, mostly Vietnam era folks, may that candle at the table continue to burn in our hearts. We don’t forget you Sam and Timothy.


  3. Dave said on September 20, 2015 at 6:46 pm

    The reality here in Europe right now seems to be that the people who benefit most from all the brilliant tools for privacy and security are: terrorists, jihadists, paedophiles, drug barons, hit men, enslavers, human-trafficers, [the list goes on].

    I’d like to keep all my communication secure and private, but the price is too high. I’m not going to oppose our spy programs on the basis that the future might be like 1984. The spy programs probably already saved my life at least once and without the hard-working people at these intelligence centres, there wouldn’t be a future for the free world anyway. Any future without freedom isn’t worth having.

    1. DonGateley said on September 22, 2015 at 10:51 pm

      If only there were a way to guarantee that the information gathered is used only for security against terrorism and not for general purpose law enforcement which has proven itself highly error prone and to be enforcing laws that are inhumane and completely illogical. Not to mention the psychopathic and irregular punishment regime used in some countries like the U.S..

      When I no longer have reason to fear my government’s irrational and savage behavior toward its citizens I will be far more likely to accept surveillance.

    2. Ann said on September 21, 2015 at 2:25 pm

      And you completly forget the lates UN report that our pricacy level is already lower then in the 1984 novel.
      go figure.

    3. Womble said on September 20, 2015 at 8:34 pm

      I think this is probably the way any adult who is capable of rationalizing his thoughts will view the situation. Sadly the internet rarely reflects this.

    4. animas said on September 20, 2015 at 8:27 pm

      The problem is most laws are up to date in regards to internet privacy. The courts are loosy goosey in what government can do with it meta data collections. You might think that you have nothing to hide, but modern government is so onerous, interpretation of law so broad, everyone, I mean everyone breaks laws without knowing it and whether you actually get in trouble with them is based on what bureaucrats choose to emphasis or clamp down at any given time.

      1. Womble said on September 20, 2015 at 8:48 pm

        Oh! you brought anecdotal evidence.

    5. MdN said on September 20, 2015 at 8:03 pm

      I don’t see how spies from other countries ever saved me, quite the contrary, and even in my (supposedly democratic European) country I have to be careful about what I say and where. If not for the government, then for the regular people (and occasionally forum admins and site guards) who generally don’t like anyone who is a bit different. Once I needed Tor in a case of domestic violence too…

      And as they say ”Those Who Sacrifice Liberty For Security Deserve Neither.”

    6. anon said on September 20, 2015 at 7:34 pm

      You’re conveniently forgetting people like whistleblowers.

  4. anon said on September 20, 2015 at 6:09 pm

    Be careful.


    On 3 July 2014, German public television channel Das Erste reported that the NSA’s XKeyscore surveillance system contains definitions that match persons who search for Tails using a search engine or visit the Tails website. A comment in XKeyscore’s source code calls Tails “a comsec mechanism advocated by extremists on extremist forums”.[11][12]

    On 28 December 2014, Der Spiegel published slides from an internal NSA presentation dating to June 2012 in which the NSA deemed Tails on its own as a “major threat” to its mission, and when used in conjunction with other privacy tools such as OTR, Cspace, RedPhone, and TrueCrypt was ranked as “catastrophic,” leading to a “near-total loss/lack of insight to target communications, presence…”[13][14]

    1. Robert said on September 21, 2015 at 12:23 am

      Just use https://startpage.com for your search and a VPN.

    2. Robert said on September 21, 2015 at 12:06 am

      Torrents are the best way to go. No man in the middle attack but you still need to verify the hash.

  5. Robert said on September 20, 2015 at 5:07 pm

    Booting onto a TAILS USB thumb drive after wardriving around for open WIFI provides complete anonymity providing you don’t do something stupid like log onto FaceBook with it. Great tool for whistle blowers and the government alike!

    1. Robert said on September 20, 2015 at 11:57 pm

      …and once your done sending your message, for extra security, wipe the usb several times and throw it away if for complete anonymity. The USB drive is only ten bucks.

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