Anonymity Install Tails OS on USB.

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What is Tails​

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Tails or The Amnesic Incognito Live System is one of most secure portable operating systems (OS). Developed based on Debian GNU/Linux, it protects you against surveillance, censorship, advertising, and viruses. Unlike typical operating systems like Windows, Linux, etc., that use the hard drive to boot, Tails starts using a USB drive and turns your computer into a secure system. Because of the protection it provides, it has widespread usage among many people who have a dire need of online privacy and security. Journalists and hackers are at the top among people who use it. The most controversial example is the NSA whistleblower Edward Snowden, who has claimed to have used Tails to leak secret files of the NSA.

How Does Tails Work​

Tails are installed on a USB drive to boot up the OS using the USB stick without using the machine’s hard disk. Thus, it's independent of the current OS installed in the machine. It encrypts your files and internet usage and nothing gets saved on your HDD or SSD. So, after you shut down your computer, you will never leave any trace of anything you did or accessed on the machine you have the Tails USB plugged into.

Privacy​

Tails uses a Tor network for all the internet activities encrypting and anonymizing your connection. Because of this, third parties will not know what websites you are visiting. Moreover, advertisers cannot learn about your browsing habits as Tor allows you to be anonymous and change your identity if you need. In addition, Tails provides a set of software applications like LibreOffice, where you can work on sensitive documents, OnionShare, Thunderbird and many more.

Persistent Storage​

Once you are disconnected from Tails, everything you did disappears, including the saved files. But you have the option to save the files persistently in its persistent storage. Everything in the persistent storage will be encrypted with password protection making everything in it secured and anonymous. Let’s see how to install Tails on a USB stick.

How to Install Tails on a USB​

What are the system and device requirements?​

• A USB drive. with at least 8GB of memory.
• Your computer should have at least 2GB of RAM.
• About half an hour of your time to install Tails and time to download around 1.2 GB of data.
• Another device like a mobile phone, tablet or another PC to read and follow these instructions while installing.

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Downloading Tails​

First, Download Tails from the official Tails website’s download page, selecting your operating system correctly.
You can either directly download Tails from USB Image or download through BitTorrent which will be much faster.

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Verify Tails Download​

After the download, if you downloaded directly, verify the download by clicking on "Verify Tails". Then select the USB image you downloaded. After that, the page will run the check. This step ensures that the download is not a malicious tails USB image. Verification from the Tails page is based on a Javascript code embedded in the Tails download page. You don't need this step if you download through BitTorrent because BitTorrent will automatically verify the download using checksum. You will get the following successful verification notification if the verification is successful.



Download a USB installer
Next, you need to download a USB installer Etcher to write the Tails ISO image downloaded and create a bootable USB flash drive.

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Install Tails​

Now we have all the things gathered to install Tails. Plug your USB device into your machine. Next, click on the downloaded Etcher installer to start Etcher.

Step 1: Click the Select ‘Flash From file’ option. Then, select the Tails USB image, which should have a .img file extension that you downloaded earlier. You can also choose Flash from the URL option if you choose to download Tails from another mirror.

Step 2: Next, click on ‘Select Target.’ Etcher will list all the connected USB drives and automatically selects a USB stick.
Select the USB drive you want to install Tails on from the list.

Step 3: Finally, click on ‘Flash!’. Etcher will Flash your USB drive with Tails on your selected USB, which should take only a few minutes. After the flashing completion, Fletcher will automatically validate the installation. Upon successful completion, it should display the following message. After that, close the Etcher window. Important: After you complete the installation, open this guide from another device because you won’t be able to access this when you run Tails.

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Restart your computer on Tails​

• In windows, click on the Start button.
• Next, while selecting the Power -> Restart option, press and hold the Shift key, then you will get a window with options to select the ‘use a device.’ option. If you do not get this option, find the boot menu key according to your computer model and shut down the computer. For example:
  Asus: Esc
  Dell: F12
  HP: F9
  Lenovo: F12
  MSI: F11
  Samsung: Esc, F12, F2
• While you start the computer, press the boot menu key identified in step 2 immediately several times.

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If the boot is successful, you will get the Boot Menu with a list of connected devices as in the above image. Then select your USB drive and press Enter. If it starts another OS installed on the computer, then restart it again as in step 3. If your machine successfully starts on Tails, you will get the boot loader on-screen and Tails will automatically begin showing the welcome screen.

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Configure and Start Tails​

You need to configure language and region settings in the Tails welcome screen as shown in the following image and click on "Start Tails".

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How to Connect to the Internet?​

For secure browsing, you can enable wifi and use the Tor browser for web surfing. For that, open the settings menu in the top-right hand corner:



Select the Wi-Fi Not Connected option and then select Network.



After selecting the correct wifi network, the Tor Connection screen appears to help you connect to the Tor network.



After successfully connecting to the Tor browser, you can safely surf the internet. If you want to send any saved files through email, you need to keep the files in the "Tor browser folder". Otherwise, Tails doesn't allow you to access any file in the default home directory.

How to create persistent storage on Tails?​

Everything you save inside Tails will vanish after you have shut it down. Thus, you can create persistent storage if you need to keep them persistently.

• Click on the applications menu in the top-left corner and choose ‘configure persistent volume’. Then you will get the following persistent volume setup window.
• Insert and verify a passphrase according to the requirements.

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• Click on the Create button and Tails will give you a list of features of Persistent Storage. Select only the features that you require.
• Click Save.
• Shut down the computer and, as explained earlier, restart your Tails USB drive.
• This time, you will get the following welcome screen consisting of an option to input your persistent storage passphrase.

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• Select your Language & Region settings.
• In the Encrypted Persistent Storage input box, enter the passphrase you have configured earlier and unlock the Persistent Storage for the current working session.
• Click on Start Tails. Within a few seconds, you will get the Tails desktop.

There is a Persistent folder in the home directory where you can now save all the working files, images, etc. You can open the Persistent folder from Places -> Persistent. Make sure to take a backup of the persistent folder because the USB stick can become corrupted at any time.

 

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How to Install Tails on Two USBs?​

You can also use two USBs to install and run Tails. Using two USBs is to use the Tail installer for incremental updates and create a secure encrypted persistent storage. You can use just one USB drive if you do not need encrypted storage. For this, you need two USB drives of at least 4GB of storage each. Install Tails as described above on the first USB.

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Create the Second USB​

• After installing the first USB, plug in the second USB and restart your computer with Tails. Select Tails from the boot menu.
• Then, after the Tails welcome screen appears, select the language and region and start Tails.
• Within a few seconds, the Tails desktop will appear - at this time, insert your second USB.
• Finally, open the “Applications” menu in the upper-left corner of the desktop. Next, click on “Tails” -> “Tails Installer”.

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• Choose “Clone the current Tails”. Once you click it, you’ll be able to select your second USB from target USB sticks and confirm the installation.
• After the installation completes, you’ll have another Tails USB.
• Remove the first USB and restart the PC back on the second USBTails. You’ll see Tails starting on it successfully.

Summary​

Tails are one of the most secure operating systems in the world. You can use it on any computer without your activities being tracked. Once installed, you can utilize its pre-installed software for all your anonymous activities, including the Tor browser to connect to the internet. This article provided a step-by-step guide on installing and running Tails on a USB stick and how you can access the Tor network and create persistent storage.

2024 Update: The details described in this guide remain unchanged and should be up to date. 

I would only like to address a few questions.

After installing tails on a USB, can the USB boot within a VM environment?
- The USB will boot on the machine you inserted the USB into. It can’t connect to a VM or a different server.
Is it possible to create only the persistent volume on a second USB?
- There is also no point in doing this, even if it would be possible. What you could simply do is copy all the files from the persistent volume onto a second USB and encrypt it. It’s the exact same thing. You can save the data from the persistent volume on any device you want, but you need to use maximum opsec protocols.

Frequently Asked Questions​

Can you use Tails without a USB?
- You can also use a writable DVD. You can right-click on the Tails ISO image in windows, select ‘Burn Disk Image” and select the Disk burner drive. When rebooting the machine, select the appropriate DVD drive.

Can you install Tails on a hard drive?
- Tails has been designed to run live on removable media like a USB or a writable DVD. Thus, it's not a recommended installation method.

Is Tails traceable?
- Tails has a sound security system allowing you to leave no digital footprint on your activities. But there can be loopholes. For instance, you are using a weak password for persistent storage. Also, if you log in from Tails into some of your social media associated with your real identity, Tails will not protect you.

 

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VPN with Tails - The Basics You Need to Know​

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Should you use a VPN with Tails?​

Yes – If you pick a privacy-focused VPN and exclusively use that VPN with Tails only and never for any other purpose whatsoever.
No – If you use your Tails VPN on other occasions, such as unblocking streaming sites on your regular OS.

In other words, you need a dedicated VPN that you use for Tails exclusively. If you use a VPN with Tails but then also use that VPN for your regular internet activity on your regular OS (where you are logged into Gmail, etc.) then you can potentially negate the privacy enhancements Tails offers to you. You should preferably register this account from a clean device or OS install or if you want to go even further, while being behind to another VPN connection. You can also pay with cryptocurrencies bought either from a local seller or a local cash-only ATM. And finally, you should get a special VPN router on which you can install your VPN and then exclusively use that router when you use Tails. This is because most VPNs don't natively run on Tails OS directly.

Pros and cons of using VPNs with Tails​

The Tails organization doesn’t recommend using VPNs as a replacement for Tor, as their goals are incompatible. However, certain use cases might warrant using a VPN with Tails for even greater benefits. To experience the best of both technologies, significant modifications would have to be made to get VPN to work with Tails. There are two primary ways to VPN with the Tails operating system.

1. Tails → Tor → VPN (VPN over Tor)​

This method adds a VPN hop after the Tor network’s end.

• It enables access to services and features you could otherwise get only through a VPN.
• You can access services and websites Tor would otherwise block.

There are many disadvantages too when using a VPN connection after Tor.

• You have access to no Tor-hidden services.
• If the Tor network gets compromised, your real IP address will be leaked.
• If third parties or other providers want to flush you out, they’ll only have to focus on breaking the VPN, not the whole Tor network.

2. Tails → VPN → Tor (Tor over VPN)​

Here, the VPN connection is established before connecting to Tor. This method offers many benefits.

• You can use Tails at airports.
• VPNs can help access Tor on censored networks.
• This enables customers to connect when Tails is unusable to their internet service providers (ISPs) or when ISPs have blocked the use of the Tor Browser.
• The Tor network treats your traffic as originating from an anonymous VPN service.
• If Tor gets compromised, you’ll still have a staunch defender in the form of the VPN server protecting you.

Despite the benefits of using a VPN connection before the Tor network, there are still some reasons why using a VPN isn’t recommended.

• If the VPN network is compromised, your data could potentially be exposed to third parties.
• The best VPNs are services you must subscribe to and pay for.
• VPNs may introduce a permanent entry guard if they’re set up before the Tor network.

Using Anonymous OpenVPN with Tails​

Anonymous VPN offers security services for many platforms, including Windows, Linux and macOS.

Prerequisites​

Unlock and configure Persistent Storage.

• Unlock persistent storage at the Welcome page by adding a passphrase.
• Add the VPN application you’ll download later, to the persistent storage.

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Set an administrator password.

• Find the administration password option under “Additional Settings” by clicking the “+” button.
• Set and confirm the password; you’ll be prompted to enter this in the terminal for many operations.

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Configure your internet connection.

Steps​

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Method 1:

• Purchase a VPN.
• Download and install a Dedicated VPN.
• After installation is complete, download the Dedicated VPN keys.
• Rename DeicatedVPN**.ovpn as tov.ovpn and copy them to the persistent storage.
• Download a script to connect OpenVPN in Tails and copy it to your persistent storage as tails.sh.

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• Open a terminal where these files are located (Persistent Storage) or navigate to the folder where these files will be located after opening the terminal.
• Switch to root.

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• Enter the command chmod +x tails.sh to set the execution rights.
• Run the tails.sh script file with ./tails.sh

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• Enter your username and password to authorize the VPN connection.
• Upon successful completion, restart Tor and ensure it works by entering the relevant commands.

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Method 2:

• Open the Synaptic Package Manager.
• Search for OpenVPN under the “Not Installed” tab.
• Check all the packages and mark them to be installed.

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• Apply the changes.

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• Configure your VPN.
• Add the configured ovpn file to VPN in the network settings.

Is using VPN with Tails is bad?​

The Tails VPN Support page insists that combining Tails and VPNs is bad. Replacing Tor with a VPN is a bad idea as well. As shown earlier, setting up a VPN isn’t too straightforward. If you’re inexperienced, it’s easy to make mistakes during the process. Disabling Tor is a bad idea, but VPNs aren’t intrinsically bad or lacking in security, as an official statement on the Tails VPN Support page suggests.

Example:

If you use Bitcoins to purchase a subscription to a reliable VPN, then the level of security you get is at least on par with that of Tor. Data packets go from the computer to the VPN and then to the Tor network by a permanent entry guard, which creates an endpoint server to receive data before reaching the Tor network. The connection is encrypted by the VPN. Therefore, there’s little difference between a permanent entry guard and a direct connection from the computer to the Tor network. The attacker must bypass the VPN’s security if Tor is compromised. This is much safer than accessing Tor directly. Almost no VPNs work directly with Tails. But it’s possible to overcome this with a VPN router.

Risks of using VPN over Tor Network​

Use VPN with Tails or a Tor network only when necessary, as this may weaken your anonymity and cause other problems if not configured properly. When considering a VPN, definitely consider the use cases previously discussed.

- Circuit Switching isn’t supported when using a VPN over the Tor network.

Internet traffic goes through different exit relays when using a Tor network. This means network requests have different paths or addresses to access the internet. If your Tor network gets compromised, third parties will find what you requested and from where. However, using a VPN introduces a permanent exit node for internet traffic, allowing others to identify your data’s location.

- The anonymity of the network built with a VPN over Tor greatly depends on the VPN’s anonymity.

People prefer to use Tails because of its anonymity and because it doesn’t trust the services of other applications in securing user privacy. However, if you think adding one more hop with a VPN to the process of what Tails does will increase your safety, you’d be mistaken. The purpose of using Tails is wasted if your VPN provider sells you out. Make sure the VPN you choose is reliable and trustworthy.

- Use a VPN over the Tor network only when necessary.

When using a VPN service over Tor, two instances are established in your machine: one will let you route VPN over Tor and the other will use Tails normally with Tor. It might be inconvenient to go through CAPTCHA so often, but you should always use the VPN instance only when you absolutely must. Some websites may also block VPN users as well. And if you’re new to VPN and Tails, aside from the recommendations outlined here, it’s still a good idea to go through all documentation carefully.

Conclusion​

Tails with Tor Browser might answer many of your security and private browsing concerns. Although there’s no consensus about whether it’s a good idea to use Tails with a VPN, the combination may be extremely helpful when used correctly. If you want to track your traffic or eavesdrop on your online conversations, setting up the Tails OS to go through the VPN and then to the Tor Network will cut all access routes to you. This setup will give you peace of mind and keep you out of harm’s way permanently.