Improve admin workstation updater GUI error handling

Increase the time it will wait for tailsconfig to run.

Don't say the admin password was wrong on tailsconfig
timeout. Instead, look for sudo in the output to determine if an
incorrect password was given.

Add a new message explaining that tailsconfig took too long, and don't
say "Exiting upgrade" when an incorrect admin password was given, as
the updater is not exiting, and in fact we're telling the admin to try
again.

Make sure the failure reason was cleared on each attempt.

journalist_gui/journalist_gui/SecureDropUpdater.py

@@ -128,26 +128,29 @@ def run(self):
         tailsconfig_command = ("/home/amnesia/Persistent/"
                                "securedrop/securedrop-admin "
                                "tailsconfig")
+        self.failure_reason = ""
         try:
             child = pexpect.spawn(tailsconfig_command)
             child.expect('SUDO password:')
             self.output += child.before.decode('utf-8')
             child.sendline(self.sudo_password)
-            child.expect(pexpect.EOF)
+            child.expect(pexpect.EOF, timeout=120)
             self.output += child.before.decode('utf-8')
             child.close()
 
             # For Tailsconfig to be considered a success, we expect no
             # failures in the Ansible output.
             if child.exitstatus:
                 self.update_success = False
-                self.failure_reason = strings.tailsconfig_failed_generic_reason  # noqa
+                if "[sudo via ansible" in self.output:
+                    self.failure_reason = strings.tailsconfig_failed_sudo_password
+                else:
+                    self.failure_reason = strings.tailsconfig_failed_generic_reason
             else:
                 self.update_success = True
         except pexpect.exceptions.TIMEOUT:
             self.update_success = False
-            self.failure_reason = strings.tailsconfig_failed_sudo_password
-
+            self.failure_reason = strings.tailsconfig_failed_timeout
         except subprocess.CalledProcessError:
             self.update_success = False
             self.failure_reason = strings.tailsconfig_failed_generic_reason

journalist_gui/journalist_gui/strings.py

@@ -25,12 +25,15 @@
                              "Contact your SecureDrop administrator "
                              "or [email protected] immediately.")
 tailsconfig_failed_sudo_password = ('Administrator password incorrect. '
-                                    'Exiting upgrade - '
-                                    'click Update Now to try again.')
+                                    'Click Update Now to try again.')
 tailsconfig_failed_generic_reason = ("Tails workstation configuration failed. "
                                      "Contact your administrator. "
                                      "If you are an administrator, contact "
                                      "[email protected].")
+tailsconfig_failed_timeout = ("Tails workstation configuration took too long. "
+                              "Contact your administrator. "
+                              "If you are an administrator, contact "
+                              "[email protected].")
 install_update_button = 'Update Now'
 install_later_button = 'Update Later'
 sudo_password_text = ("Enter the Tails Administrator password you "