Tails Installation Assistant - What do you think about it?

Originally published at: https://www.whonix.org/blog/tails-installation-assistant
Tails (The Amnesic Incognito Live System) has now a Tails Installation Assistant. What do you think about it? Does it improve or worsen usability?

I am wondering, if something like that would be useful for Qubes OS to ease download and installation.

Something similar has been discussed for Whonix some time ago, although with a different outcome.

Historic blog post and forum discussion:

Old page:

Good day,

well, you know me, I’m all for trying out such new ideas and seeing how this is actually just a simple link based solution, dressed up nicely, we could accomplish this fairely easily using the tools we already have. Would help usability by a huge degree, though before I can try something in that degree, I really need to come arround and finish my current work on improving usability.

Have a nice day,


yeah it was a good change to Tails website by adding this. Qubes need installation tutorials more than installation guidance. but sure that would be useful for them to have a similar design as Tails.

but the one who really need this design much to have , is Whonix. which is sadly i have lack of knowledge on how to make this to become true inside our website.

Don’t wonder, I sometimes ask for opinions without stating mine first. So just by asking it’s not sure I will like the idea myself at that point.

Perhaps since I am a whole different type of user, I am not the best one to make the judgment. But I find this thing confusing.

start the journey -> debian or ubuntu -> install from debian or ubuntu -> let’s go -> click “I am already on firefox” -> breaks, since it does not work with noscript -> ok, let’s do it without noscript

start the journey -> debian or ubuntu -> install from debian or ubuntu -> let’s go -> click “I am already on firefox” -> install firefox extension -> downloads and verifies tails, great -> now I am supposed to install Tails Installer from Debian backports -> point the installer to the iso

start the journey -> other linux -> then you need intermediary Tails installation probably for some obscure technical reason they could not overcome yet.

All in all kinda a lot steps. Imho cumbersome.

Anyhow. Some things can be learned from it.

  • The page Which operating system are you installing Tails from? might be useful to adapt for Whonix. - I wonder if that would provide more usability than our current supported platforms table?

  • I wonder if installing the firefox addon and using that for downloading would be simpler than our current download table. That firefox addon for downloading Tails is supposed to work in firefox version 38.0.1 or Tor Browser 5 or higher. However, it would not work for let’s say users of chromium or other browsers. There it would just download the addon as xpi file which would not work. From there the user would be lost.

  • What I am concerned here is adding more layers of complexity, more options that ultimately lead to more than less confusion.

  • What I find a good idea on the Installing Tails on a USB stick from Debian or Ubuntu using the command line page is to have the Verify the Tails signing key instructions on the same page as download, verification and installation instructions.

  • What I find a horrible idea is the following quote.

To follow these instructions you need to have your own OpenPGP key.

To learn how to create yourself an OpenPGP key, see Managing OpenPGP Keys by Riseup.

To require having your own OpenPGP key just for the sake of verification is a huge overhead that I am sure needlessly deters users. They probably want to avoid the following message. (That we have documented in Whonix OpenPGP verification instructions.)

gpg: WARNING: This key is not certified with a trusted signature!
gpg: There is no indication that the signature belongs to the owner.

Anyhow. Documenting the above confusing message is, I am sure, the much smaller evil than linking to instructions on how to create your own gpg key.

  • To say it looks nice from the first impression is one thing but to really look into the details before adapting is a whole other story.

They found a cleaner looking way to route yourself through all the workarounds, but it’s still a collection of workarounds with many points of failure.

Some workarounds probably have a solution that one group can solve†, other problems are big (secure downloading over the internet).

One way to think about this is: “What would the ideal solution look like?” I think that’s an .exe installer for windows, some generic linux installer, and a mac pkg. Downloading it securely will be hard, but once the user double clicks, it could be an obvious step-by-step process.

† I’m suprised about how hard it is to install with windows. A third party usb installer to make a live disk, then a second usb stick to use the “real” usb installer. It is possible to install windows to a usb stick, with windows (WinToUSB), and I think it’s worth the effort if you’re main use is boot-from-usb.

I simply don’t think that we can approach “mainstream acceptance” without a simple way to install (whether it be USB boot sticks or VMs or whatever). I know we’ve gone back and forth for years about this, but as whonix/linux becomes more usable as a desktop os, the installation is becoming the biggest barrier.

I prefer the current state of affairs for our download tables. All the relevant information is just in one place. The front page could use some updated graphics to make it more visually appealing but that’s all IMO.

For users who want/need more hand holding something like the windows-installer you are working on fits that use case.

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