Well ok that was my first thought,too (boolean) so my first tests were
misleading then. I tested a little bit more and find something maybe
more useful.

When using Ubuntu 16.04.2 fresh installed and I set in
/etc/apt/apt.conf.d/50unattended-upgrades:

Unattended-Upgrade::InstallOnShutdown "true";

it seems to have no effect. Upgrades are there but they do not get installed. I 
get no plymouth message on shutdown.
Same when set to "True".

When I change /usr/share/unattended-upgrades/unattended-upgrade-
shutdown:

(line 120 again)

    # check if we need to run unattended-upgrades on shutdown and if so,
    # run it
    p = None
    apt_pkg.init_config()
before <<    if apt_pkg.config.find_b("Unattended-Upgrade::InstallOnShutdown", 
False):
after  >>    if apt_pkg.config.find_b("Unattended-Upgrade::InstallOnShutdown", 
False) == True:
        env = copy.copy(os.environ)
        env["UNATTENDED_UPGRADES_FORCE_INSTALL_ON_SHUTDOWN"] = "1"


Then it seems to work like expected.

Now when i set:

"Unattended-Upgrade::InstallOnShutdown "true";

in /etc/apt/apt.conf.d/50unattended-upgrades it starts upgrading on
shutdown (I see the plymouth message "Unattended Upgrades..."). When I
set it to "false" or just outcomment the whole line it do nothing on
shutdown. So exact the behavior I expect.

Well I'm not a python expert but it seems to me that the <if True> thing
works not as it should or maybe has changed in python3 some how? It may
affect all other statements as well then (like MailOnlyOnError etc) but
I haven't tested them yet...

With the above patch it works for me as it should. At least for the
shutdown setting.

-- 
You received this bug notification because you are a member of Ubuntu
Touch seeded packages, which is subscribed to unattended-upgrades in
Ubuntu.
https://bugs.launchpad.net/bugs/1661611

Title:
  apt/unattended-upgrades stalls shutdown

Status in unattended-upgrades package in Ubuntu:
  Incomplete

Bug description:
  When unattended-upgrades is installed, 9 out of 10 shutdowns/reboots
  hang while "starting unattended upgrades shutdown". This hang stalls
  the shutdown process for 5-10 mins.

  If I disable unnattended-upgrades via the /etc/apt/apt.conf.d/20auto-
  upgrades and/or 50unattended-upgrades, the problems occurs.

  If I terminate the service before shutdown/reboot (sudo service
  unattended-upgrades stop) the problem still occurs.

  If I remove the package (sudo apt remove unattended-upgrades) the
  problem no longer occurs.

  This occurs on a freshly installed version of Ubuntu Server 16.04.1
  (both unattended-upgrades installed via install GUI or manual install
  of unattended-upgrades)

  Both Kern.log & syslog do not show the shutdown process (I believe
  because the filesystems have already unmounted)

  Original report: http://askubuntu.com/questions/878630/apt-unattended-
  upgrades-stalls-shutdown

To manage notifications about this bug go to:
https://bugs.launchpad.net/ubuntu/+source/unattended-upgrades/+bug/1661611/+subscriptions

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