VPN with Tails – Basics You Need to Know

Tails, also known as Amnesic Incognito Live System is a Debian-based Linux operating system. Its main purpose is to preserve your privacy and provides you anonymity. This is achieved by routing your internet traffic through Tor- a software which allows you to browse the internet anonymously. Furthermore, the tails is also equipped with email client, instant messaging client and an office which are all pre-configured with security.

Tails is easy and simple to use that even beginners could use and navigate. Through this tool, you could prevent third party apps from tracking you and checking what you are doing through your online activities.

To learn more about Tails and Tor, you could go to the following sites:

1. Tor browser

2. Tails Operating System

With working knowledge on VPNs, we shall now focus on how to use it with tails. This way, you will have more protection online.

First, what are the advantages of using Tails?

  1. It lets you skip setting it up. Tails is pre-configured to route all network traffic through Tor.
  2. It protects your privacy and secures your browsing history whenever you use someone else’s device/machine.
  3. It secures your PC
  4. It leaves no trace of the sites you have visited, passwords that you have entered and opened files.
  5. It allows you to access varieties of software to work with.
  6. Saves files and configures it to an encrypted storage.
  7. Tails could block apps that try to connect the internet without Tor and deletes all memory once you shut down your computer.

Pros and Cons of using VPNs with Tails

Since the goals of tails are incompatible with VPNs, it does not recommend using VPNs as a replacement for Tor. But, in some cases, you would might want to use a VPN with tails as it offers more and greater benefits.

There are two ways to use a VPN with tails operating system:

1. Tails-Tor-VPN (VPN over Tor)

This method allows you to add a VPN hop after the Tor network’s end.

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

Using this method also comes with disadvantages as well and they are the following:

  • You will have access to no Tor hidden services
  • If there are third parties that would flush you out, they will only focus on breaking the VPN.
  • Your real IP address will be leaked if your Tor network gets compromised.

2. Tails-VPN-Tor (Tor over VPN)

In this method the VPN connection is established before connecting to Tor. This also comes with numerous benefits.

  • You could use tails at airports
  • It allows users to connect when tails is unusable to their Internet Service Providers (ISPs) or when ISPs block the usage of Tor Browser.
  • It could help access Tor on censored networks.
  • Even when your Tor gets compromised, you will still be protected in terms of your VPN.

Just as like the first method, this second method also has several disadvantages.

  • Best VPNs are usually paid VPNs.
  • If your VPN is compromised, your data could be exposed to third parties.
  • Some VPNS may introduce a permanent entry guard if they are set up before the Tor network.

Using Anonymous OpenVPN with Tails

Anonymous OpenVPNs come with security services for numerous platforms such as Linux, Windows and macOS.

You may download anonymous OpenVPN through the link below:



– You will need to unlock and configure your Persistent Storage:

o Unlock persistent storage by going to the welcome page and add a passphrase.

o Then, add the VPN application that you will download to your persistent storage.

– Set an administrator password

o Go to administration password option which could be found under additional settings. To go to additional settings, click + button.

o Set and confirm your password. You will be prompted to enter this in the terminal for many operations.

– Configure your internet connection

Method one:

o Purchase and subscribe to a VPN

o Download and install a dedicated VPN

o Once the installation is complete, download Dedicated VPN keys

o Rename dedicated VPN.ovpn to tov.ovpn

o Copy it to persistent storage

o Download the script for you to be able to connect to OpenVPN in tails

o Copy it to your persistent storage as tails.sh

o Open a terminal where all of the files are locate. This is normally the persistent storage. Navigate to the folder where the files will be located after opening the terminal.

o Switch to root

o Type command chmod+x tails.sh. this will set the execution rights.

o Run tails.sh script file with ./tails.sh

o Type your username and password. This will authorize your VPN connection

o Once completed, restart Tor and check if it works. You could do this by entering relevant commands.

Method two:

o Open Synaptic Package Manager

o Look for OpenVPN. Usually you will find this under the not installed tab

o Check the packages and mark them to be installed

o Click apply changes

o Configure your VPN

o Add your configured ovpn file to VPN in the network settings

VPN service providers and tails

ExpressVPN – not fully tested with tails OS. Hence, ExpressVPN could not yet be installed in tails.

– Tails is Linux-based OS. You could manually set it up through PPTP on Ubantu. Take note however that this method is not guaranteed to work.

NordVPN – is incompatible with Tails.

PureVPN – not tested with tails. Therefore, it is not guaranteed to work.

OpenVPN/Anonymous OpenVPN – not directly supported but it could be set up through workarounds.

Is using VPN with tails as bad as they say?

According to the support page of tails, combining tails with VPN is not a good idea and replacing Tor with it is equally not good idea. Hence, if you are not experienced, it is easy to commit mistakes during the process. As you could have seen above, setting up a VPN is not as easy nor is it straightforward.

Though this is the case, and disabling Tor could be a bad idea, VPNs are not as bad either nor does it lack security features as stated in Tails VPN support page.

Example, if you are using bitcoins to purchase a VPN subscription, the level of security, protection and privacy will be at par with that of Tor.

Data packets will go to your VPN from your computer then it will go to your Tor network through permanent entry guard. This will create an endpoint server that will be able to receive data before reaching your Tor network.

Moreover, your connection will be encrypted by your VPN. Hence, you will find little difference between your permanent entry guard and direct connection from your computer to your Tor network. In other words, if your Tor is compromised, your attacker will have to bypass the security levels imposed by your VPN. This means, it is much safer than being able to access your Tor directly.

Risks of using VPN over Tor Network

We highly recommend that you use a VPN with tails or with Tor network only when it is only absolutely necessary. The reason behind this is it could weaken your anonymity and could cause other problems if you have not configured it correctly.

Circuit Switching is not supported when you use a VPN over the Tor Network

Internet traffic goes through exit relays whenever you use a Tor Network. Hence, network requests will have different paths and addresses to access the internet. However, if you use a VPN, a permanent exit node is created for your internet traffic which allows others to identify which location your data is coming from. If your Tor is compromised, third parties will know what you have requested and from where.

The anonymity of your network is built with VPN over Tor depends on the VPN’s anonymity.

Some would prefer to use tails due to it being able to provide you anonymity and how it does not trust any services of other applications in terms of user privacy. If you would like to add one more tool with a VPN to process Tails to increase your security and privacy, unfortunately, this would not be true as if you use a VPN the purpose of using tails will be wasted. Ensure that if you would want to use VPN, choose one that is highly reliable, effective and trustworthy.

Use a VPN over the Tor network only when necessary

If you use VPN service over Tor, you will be able to establish route VPN over Tor and use tails normally with Tor. This could be inconvenient if you have to go through CAPTCHA often. Hence, it is recommended that you only use VPN over Tor network only when it is necessary.

Renee Biana

VPN Pick brings you all the latest vpn news, reviews and discounts.

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