Setting Up Tails OS for Web Security and Anonymity

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  • ToolAA

    Ultimate Member
    MDS Supporter
    Jun 17, 2016
    10,500
    God's Country
    I know we have a few browser threads already but I wanted to share my experiences with Tails OS and offer some links to those who would like to experiment with this tool.

    First for those who do not know what Tails is, it’s a bootable, portable Linux operating system that runs from a USB thumb drive (or burned to DVD ROM). The OS is very lean and is reported to run on just about any PC/Mac hardware platform including hardware that is 10-15 years old. If the computer does not have a working HD, but you can boot from the USB, you can likely use the device to run Tails OS.

    The Tails OS includes a set of basic useful desktop applications like; Word Processor, Spreadsheet, graphic and photo editors and more.

    It also includes an integrated TOR web browser.

    Additionally is you are using a USB thumb drive with at least 16gb you can create an encrypted persistent storage area accessible to the Tails OS.

    Read the basic details here.
    https://tails.boum.org/

    How is the Tails OS more secure and anonymous than the average computer. The main reason is that each time you end a Tails session, ALL data accumulated during the session is completely deleted. No information is ever “saved” in any temporary folders, registry files, web cache, cookies, trackers, passwords, browser history. When you remove the USB drive or power off the device, nothing is saved. When you restart a new session you always start with a Clean Virgin OS!

    The Tails OS offers users the ability to security lockout any modifications to the OS session, so that software/malware cannot be installed without the user intervention. Even if something was able to penetrate the OS, it would be deleted and the OS reset once a new session was started.

    Like any system there are still vulnerabilities, so it’s important to really read the available information and learn how Tails and TOR works, but suffice to say it offers significant improvements over the average mobile phone, PC or Mac.

    In in order to create a Tails OS USB drive you need to start from a computer connected to the Internet and have a USB drive with suitable space. Note anything on this drive will be wiped during the Tails OS install, and you will no longer be able to use the USB drive as a Windows or MAC storage device.

    The method and instructions to create a Tails OS differ depending on the computer system you are installing from. The install took me about 2-1/2 hours, but this is not time that you must attend the device. The longest part is the writing and verification of the
    Install, but this is really unattended. I started the process before I went to bed, and spent about 10min finishing up the next morning. I used my phone to follow along the instructions as I completed each step. This is setup for someone who is mostly computer illiterate to install.

    Start here for detailed instructions:
    https://tails.boum.org/install/index.en.html


    So why do want this tool? Good question. You might think that something like this is really only needed by persons conducting nefarious acts. However in light of recent events it seems that citizens of this country are simply considered guilty by social media association. However, a more practical reason is that simply many of us have simply become complacent with respect to giving away gigabytes of personal information to unknown corporations, to use as they see fit. Previously I didn’t care that this information was being collected and used, but now I do, and I want the ability to stop the flow of that information should I deem it necessary. While there are a lot of ways to achieve this on many of the devices we use, Tails OS offers most of the tools and methods in one complete, portable package.

    Additionally, I recently learned about browser fingerprints. Basically your browser shares detailed information about your hardware, software and OS settings which can be used to tie your activities online to your computer and potentially your location and your. If you do not know what a browser fingerprint is, read about it here: https://coveryourtracks.eff.org/learn

    Using the online testing tool in the link above, I ran a few test to see how Tails OS compares to my iPhone. The more “Unique” your profile is, the less secure and anonymous you are.

    Here is the results testing my iPhone using the default Safari browser and without my VPN active. My browser shared 18.16 bits of identifying information and my browser was unique in 1:291,995 browser sessions. So that, pretty identifiable. Sort of like that one guy wearing a purple sparkle body suit and red clown wig at a Muslim pilgrimage to Mecca!

    c0573a74b7e0e0c931e49528246ed78d.jpg


    Here are the results from my phone with my VPN set to a major US City and using Duck Duck Go as my browser. Much better almost a 20 fold improvement, but still pretty unique.

    edcc2acad2142884e3f511703bae0605.jpg


    Here is a test using Tails OS and the TOR browser with my MAC address shared over WiFi. A 160 fold improvement over my iPhone default profile.

    d3ce4768790d469e26e9fbfda3495626.jpg


    Finally, I conducted a test setting the TOR browser to the highest security settings and using a CAT5 ethernet connection and spoofing my MAC address. This is a whopping 4000 fold improvement. Basically your browser fingerprint us almost unidentifiable when you consider that there are billions of internet connections ever day.

    634034ac0513b0fc0f1120284708e22c.jpg


    It may be possible to improve the results further, but I am not yet experienced enough nor do I think it’s really necessary or worth the time to push further. The purpose of this was to understand the difference between Tails OS and my rather generic iPhone to simply illustrate a point.


    Finally what is my current practical use case for Tails OS?

    Well first I used to keep a USB drive with copies of personal documents, will, titles and deeds, ect as part of an emergency preparedness kit. This has been replaced with a Tails OS usb which offers even greater security along with the ability to access the information from any crappy company I find available.

    Second, I purchased a very small USB key shaped drive that I keep on my key ring. It has copies of some important documents, books, and other stuff I figured I might need for some reason. In also figure if I ever need computer access from some unknown computer, say at work or an internet cafe, I could potentially reboot the device using Tails and have my own secure session without giving the device owner many opportunities to store information from my use session.

    Lastly I keep a small drive at home plugged into my laptop. This is the only way I will access my proton mail account and will be the only way that I will browse GAB. I also plan to setup new Reddit, twitter and social media accounts linked to another Proton Mail address and I will only visit those sites using the new secure account info through Tails.

    Anyway I encourage some of you to check it out and share any findings or ideas. This is NOT my area of expertise so I still have a lot to learn.

    Cheers.
     

    Rockzilla

    Ultimate Member
    Feb 6, 2010
    4,516
    55.751244 / 37.618423
    Nice Post...Used Tails for some time, use a lot of live
    OS's / disks.Works good, v4.15.1 is the current one.
    I use ventoy to put all my images (ISO's) on a Thumb
    drive, boot from it, pick what I want to run from the
    menu and done. Can add / remove images as needed.
    Backups...here, there and everywhere. Encrypted.
    If your data is important, then a Iron Key thumb-drive
    may be what you need..it ain't cheap.

    -Rock
     

    ToolAA

    Ultimate Member
    MDS Supporter
    Jun 17, 2016
    10,500
    God's Country
    I wonder if Tails would run OP25 which is a pure java program to discover phase 1 and phase 2 radio systems and related talk groups.


    If the program runs on Debian Linux then it might run in Tails but Tails is not intended to keep additional programs in memory. So you would have to reinstall the program each and every time you wanted to use it.
     

    ToolAA

    Ultimate Member
    MDS Supporter
    Jun 17, 2016
    10,500
    God's Country
    The biggest weakness I see is the use of a USB drive. Since they aren’t read only devices, they can be compromised.

    Since your question is TailsOS specific, I moved my response to this thread.

    Unlike a simple windows FAT formatted USB the TailsOS resides on the USB essentially as a rom. Someone would physically have to create a modified version of Tails and somehow swap it without you knowing. When you download the TailsOS installer, the file hash must be checked before the installation will continue.

    Each time you start Tails, it’s like you are booting from a virgin OS. No files in the OS can be modified. Tails users can choose to enable a portion of the USB drive as protected and encrypted storage. That storage area is only accessible from within Tails.

    I did find a post online explaining that using a DVD version of Tails may be very slightly more secure.
    https://security.stackexchange.com/...s-a-usb-flash-drive-vs-dvd-for-os-tails-linux

    Part 2: Who is behind it and what is their motivation? That’s the other question I’d want to have answered. Can they be trusted?

    The first rule of protecting your privacy is “Trust No One”.

    You can read more about TailsOS, their history and mission here. https://tails.boum.org/contribute/mission/


    Our mission and values
    Our mission is to empower people worldwide by giving out an operating system that protects against surveillance and censorship.
    We make digital security tools accessible to everyone, whenever they need it: activists, journalists, freedom fighters, domestic violence survivors, and ultimately, you, whenever you need extra privacy in this digital world.
     

    ToolAA

    Ultimate Member
    MDS Supporter
    Jun 17, 2016
    10,500
    God's Country
    Coincidentally enough, here's a Distrowatch review of Tails:
    Tails 5.0

    Thanks Bill, I cross posted to this thread which has been a bit inactive for 7 months. I upgraded to tails 5.x a few months ago. I’ve been trying to create a sort of emergency USB version with some of my personal files and documents along with a few applications in persistent storage, but my inexperience with Linux is a bit of a handicap.
     

    ToolAA

    Ultimate Member
    MDS Supporter
    Jun 17, 2016
    10,500
    God's Country
    I just ran across this. Has anyone here tried it? Apparently you just install it on a thumb drive and boot your computer with it.


    Yup. I use it from time to time. I also keep a copy on a small usb drive on my car keychain, in case I need to use someone else’s computer for anything private.

    Here is a post I created a while ago.

     

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