Good and Geeky

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David Allen Wizardgold

David Allen Wizardgold

How to Be Good and Geeky One Step at a Time

Privacy and Security for Activists- Tails OS

Table of Contents

Good and geeky

Taking Privacy Security And Encryption to the Next Level

If you’ve been following this channel for a while you’ll know that I am keen to promote privacy, encryption and security. One of the easiest ways to protect your data when you’re sending emails is to use the webmail available with Vivaldi browser. An easy to use PGP service. Or you can set up encryption using email clients like MailMate or Thunderbird. If you don’t want to get into encrypted emails you could also use end-to-end encryption with messaging services like Signal, Session, Threema, Dust, Wire and perhaps Telegram. Don’t send an email when you can send an encrypted message.


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Sending Email Through a Web Browser.

I do not recommend this if you’re using one of the more open web browser applications like Chrome or Safari or Internet Explorer. Safer browsers like Brave, Vivaldi and Firefox are better. Only then is it better when you are completely sure your computer is not compromised with a key logger or other malware. What about if you need to use a computer which is not your own? What can you do to ensure your privacy and security then? Now most of us carry a computer in our pocket is not so necessary to use somebody else’s computer. There are still some edge case scenarios where you’d have to use computer equipment that wasn’t your own. What about if we could carry our computer/personalised operating system with us? This is how we take our security to the next level by using a computer which we carry around on a USB drive or an SD card.

Tails – The Portable Secure Computer Anywhere

Tails stands for – The Amnesiac Incognito Live System. What you do is to install the computer on a USB drive or an SD card which you can plug into most computers and run directly. It’s not connected to the operating system on the host computer. So theoretically even if the host computer has viruses or things like keyloggers you’ll be able to use Tails completely safely. You will be able to avoid censorship, advertising and viruses, benefiting from a digital security toolbox which is ready to use with the safest defaults. This is free software and it’s based on a Debian Linux and I have tested it to find out how easy it is to install and use.

My Experience with Tails

To get Tails you go to this webpage for Tails and download the image file to install on your portable storage. It’s about 1.2 GB in size and doesn’t take too long with a reasonable speed Internet. It’s possible to install this software image onto the USB stick using the command line interface, but it’s easier if you grab the software called Etcher. Make sure you get the latest version of this software. The reason I say this is because I was using an older version and it didn’t work. I didn’t know why it wasn’t working and I thought the problem was with the SD card. As soon as I used the latest version of Balena Etcher the process was as smooth as butter. The minimum size of your USB stick is 8 GB and I used an SD card with 16 GB and I also installed onto a micro USB with 32 GB without any problems.

Tails will run on most computers. I first tried it on my own 2018 iMac and it didn’t run. I might try again on that computer, but instead what I did was to try it on my older iMac and it ran straightaway. It has to be said that this computer system isn’t really meant for everyday working. It takes a long time for it to load and boot up. You are going to need some patience waiting for it start up and be ready to use. It was only a couple of minutes, but it’s much slower than the operating system I normally use. I would recommend using a faster rated storage device to enhance the load up time.

When you are working on the Tails system you won’t notice much difference with most of your working. The operating system is fast enough and when you work on your documents it will be just like using any computer. It will be slower with the browsing of the internet through the browser. This is because by default Tails is setup to use a Tor connection. This makes your browsing safer and more private, but will always be slower to load pages. It’s not that bad. We are using Tails more for the security than for general computer usage though. We can put up with a slower download of web pages when no one knows what you are looking at.

Setting up Persistent Storage

The amnesiac part of Tails is the way it deletes and forgets everything when you shut it down. The idea is that your SD card or USB stick can’t keep anything which could incriminate you or be used to grab data you want to keep secure. However there will be some things you want to keep. This can be files and it can be settings. This secure space is protected by a password and is not unprotected out in the open. When you log in next time you will have to give the password to get access to the persistent storage. In this area I keep the PGP keys I use. The key pair I have for sending and receiving encrypted mail and also the public keys for me to send encrypted messages to my contacts. This works well for my threat level. Someone with a higher threat level like a whistle-blower, journalist or activist might prefer not to keep anything from a session. That scenario would need a fresh operating system each time, and that’s what you get with Tails. You will have to setup a new key pair each time, but that’s quick and easy and not a problem. If you don’t keep the previously used key pair you won’t be able to read encrypted data sent to you on the last session. You will have to work around that. Anything not in the persistent storage is completely erased when you log out. Nothing is written to a hard disk.

What Do You Get With Tails

The Libre Office suite of office software in on there, along with Audacity audio recording software. The PGP works through the text editor. You can also encrypt files using PGP. There is the Tor browser which is fine, if a little slow. There is a password manager KeePassCX, which you protect with a password like I do with 1Password on Mac and iOS. Put that into persistent storage also if you wish. You get Thunderbird mail client with which you can send encrypted emails. OnionShare for sharing files over Tor. There is an app called mat2 which will remove metadata from a wide range of file formats. A digital photo could betray you by having metadata showing the location where the photo was taken. So you have a tool to clean files so they can’t be connected to you. There are all the basics you need for general computer usage. It’s also possible to add other apps as you need them, either for temporary usage or you can make them persistent.

Protect your identity when using Tails

Tails is kind of marvellous, but it’s not magic. You should use Tails sessions for only one purpose each time. This is so an adversary can’t link your activities like you logging in to a website with two different accounts. You should restart Tails if you are checking work emails and then want to check whistle blowing emails. You should still follow good security and privacy practices when using Tails.

Tails is Recommended By –

The Electronic Frontier Foundation (EFF) recommend Tails. Founders of the Tor Project recommend Tails, saying it’s a favourite companion Tool of Tor. Edward Snowden, whistle blower extra-ordinaire says Tor and Tails help you to maintain anonymity. He should know..

Who Should use Tails?

  • Activists
  • Journalists
  • Domestic violence survivors
  • Anyone who needs to avoid censorship and needs to communicate securely
  • You – For the extra privacy sometimes needed in todays digital world.

Not for Everyday Use- More for the Special Occasions

It was fun to set up and use a different and specialised operating system. I couldn’t use it everyday because many of the applications I like to use are not available. I am so ingrained into using the Mac and the applications that come with it. However, Tails is definitely something I will add to my arsenal of privacy and security protection tools. It has a reasonable and very easy-to-use implementation of PGP encryption. It’s easy to encrypt text and files manually and to add them to an application for sending to the recipient. On top of that there is the addition of Thunderbird in which you could use their implementation of PGP. It’s easier and a little bit more automatic to send and receive encrypted emails using this email client.

Encrypto to Use on the Mac

I can already use PGP and end to end encrypted messaging services to communicate safely using my Mac and iOS devices. For me the use of Tails would be for those specific situations when it was necessary to bring out the big guns. Everything within Tails is set up from the get go to be private and secure. You have to work hard to make mistakes and send something or receive something which could come back and bite you. Due to this inherent built-in safety I think it’s good for beginner users in the realm of privacy and security as well as for more savvy users. A beginner user doesn’t have to think about it too much. Set up the system on your portable storage and have it available wherever you are. This is particularly good for any user when it’s necessary to use a computer which is not yours. You don’t know how well the owner of the computer takes care of security and privacy and you can get around this by using Tails. I recommend making a Tails USB drive or SD card and always keeping it with you. Attach the USB drive to your keys or put the SD card in your wallet.


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