We started a process of rethinking Tails installation and upgrade process, identifying changes we can do relatively quickly and that have a good cost/benefit ratio, and thinking about long-term solutions.

Most of the installation issues we've identified were solved by shipping a USB image.

Problems identified in Tails installation & upgrade process


Problems below are tagged this way:

  • [fixed-by-1-big-iuk]: would solved by a smallish change to our upgrade system that would allow users to automatically upgrade through a whole Tails series such as 3.x (this idea is also known as "IUKs on steroids", "1 big IUK", "endless upgrades"), i.e. #15281 and Endless upgrades

Installation process

  • Users have to first understand a complex mental model in which they download an ISO image, have to use an installation program and create some kind of "magic USB" key.
  • Users need to turn off UEFI Secure Boot to start Tails.
  • There's a mess around what device is considered "removable": we have slightly different definitions in various places.

Upgrade process

  • Regular Tails users need to go through manual upgrades twice a year. [fixed-by-1-big-iuk]
  • It's currently not possible to autoupgrade from an older Tails version, i.e. It's impossible to autoupgrade from Tails 3.1 to Tails 3.5. [fixed-by-1-big-iuk]
  • IUK size is not efficient. Users have to download a big blob of data which can be very long over Tor.
  • On upgrade failure our recovery handling is poor.
  • Upon upgrades our user experience is poor.
  • Manual upgrades are very complicated.
  • Sometimes manual upgrades are required.
  • Our upgrade system has never been audited yet.
  • Because we instruct people not to use apt upgrade they have to wait for us to release bugfixes, and these are often made too late after the release.

Envisioned solutions to the problems that are not fixed-by-1-big-iuk: #15279, #15282, #7499.