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.
I personally recommend getting a fresh ExpressVPN account registered with a disposable email address you haven’t used elsewhere.
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 do not natively run on Tails OS directly.
Related: How to install Tails on a USB
In this article, you will learn about:
- How Tails operates and what it’s used for
- How a VPN operates and what it’s used for
- Why sometimes it’s not recommended to use a VPN with tails
- How to safely use a VPN with Tails (important section!)
You can jump quickly to the relevant sections by using the menu on the right (desktop) or the one a bit further down (mobile).
The Amnesic Incognito Live System, known as Tails, is a Debian-based Linux operating system whose ultimate goal is to preserve your privacy and anonymity. To achieve this, Tails forces all your internet traffic to route through Tor — software that lets you browse the internet anonymously. Tails are also equipped with an instant messaging client, an email client, and an office suite, all pre-configured with security.
Tails are simple and easy to use, even if you’re a novice user. With Tails OS, you can prevent third-party applications from tracking your online activities.
To learn more about Tails or Tor, follow either of these links:
We assume you have some working knowledge about VPNs. So in this guide, we’ll focus on how to use VPN with Tails to keep you secure.
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.
This method adds a VPN hop after the Tor network’s end.
There are many disadvantages, too, when using a VPN connection after Tor.
Here, the VPN connection is established before connecting to Tor. This method offers many benefits.
Despite the benefits of using a VPN connection before the Tor network, there are still some reasons why using a VPN isn’t recommended.
We recommend ExpressVPN if you want to use a Tails VPN. But keep in mind to get a new clean account and never use it for anything else other than your Tails activity.
Anonymous VPN offers security services for many platforms, including Windows, Linux, and macOS.
Unlock and configure Persistent Storage.
Set an administrator password.
Configure your internet connection.
|VPN Service||Services to Tails|
|ExpressVPN||Works if installed on a VPN router. VPN settings and configurations not fully tested with the Tails OS, so ExpressVPN can’t yet be installed in Tails. Since Tails is a Linux-based OS, you may refer to our manual setup link below using PPTP on Ubuntu, though this isn’t guaranteed to work.|
|PureVPN||Not tested with Tails; therefore, not guaranteed to work.|
|NordVPN||Incompatible, as Tails doesn’t support the use of VPNs directly.|
|OpenVPN/Anonymous OpenVPN||Not directly supported, but can be set up with a few workarounds.|
The Tails VPN Support page insists that combining Tails and VPNs is bad.
Moreover, 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.
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 or Tor exit nodes are compromised. This is much safer than accessing Tor directly.
Almost no VPN providers work directly with Tails. But it’s possible to overcome this with a VPN router.
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.
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 off all access routes to you.
This setup will give you peace of mind and keep you out of harm’s way permanently.