Automatic upgrades are broken from Tails 4.14 and earlier.

To upgrade from Tails 4.14 or earlier, you can either:

• Do a manual upgrade.

• Fix the automatic upgrade from a terminal. To do so:

  1. Start Tails and set up an administration password.

  2. In a terminal, execute the following command:

     torsocks curl --silent https://tails.boum.org/isrg-root-x1-cross-signed.pem \
     | sudo tee --append /usr/local/etc/ssl/certs/tails.boum.org-CA.pem \
     && systemctl --user restart tails-upgrade-frontend
     

     This command is a single command that wraps across several lines. Copy and paste the entire block at once and make sure that it executes as a single command.

  3. Approximately 30 seconds later, you should be prompted to upgrade to the latest version of Tails. If no prompt appears, you might already be running the latest version of Tails.