This bug was fixed in the package landscape-client -
16.03-0ubuntu2.16.04.5

---------------
landscape-client (16.03-0ubuntu2.16.04.5) xenial; urgency=medium

  * debian/patches/nutanix-kvm.patch: Update vm_info.py to include Nutanix
    hypervisor (LP: #1788219)
  * Fixes for release-upgrade (LP: #1699179).
    - debian/patches/1699179-release-upgrade-check.diff: Check if ubuntu-
      release-upgrader is running before apt-update. (LP: #1699179)
    - debian/patches/release-upgrade-success.patch: Enable landscape-client to
      survive trusty upgrade. (LP: #1670291)
    - debian/patches/post-upgrade-reboot.patch: Force reboot operation in
      case systemd fails. (LP: #1670291)
  * debian/patches/1616116-resync-loop.patch:
    Clear hash id database on package resync. (LP: #1616116)

 -- Simon Poirier <simon.poir...@canonical.com>  Tue, 27 Nov 2018
09:24:22 -0500

** Changed in: landscape-client (Ubuntu Trusty)
       Status: Fix Committed => Fix Released

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https://bugs.launchpad.net/bugs/1670291

Title:
  Landscape: Upgrade 14.04.5 to 16.04.2 fails unable to reboot

Status in landscape-client package in Ubuntu:
  Fix Released
Status in systemd package in Ubuntu:
  Fix Released
Status in landscape-client source package in Trusty:
  Fix Released
Status in systemd source package in Trusty:
  New
Status in landscape-client source package in Xenial:
  Fix Released
Status in systemd source package in Xenial:
  Fix Released
Status in landscape-client source package in Bionic:
  Fix Released
Status in systemd source package in Bionic:
  Fix Committed
Status in landscape-client source package in Cosmic:
  Fix Released
Status in systemd source package in Cosmic:
  Fix Released

Bug description:
  https://github.com/systemd/systemd/pull/10061

  [Impact]

   * When logind is not available, shutdown command fails to schedule a
  shutdown, and despite its intentions to immediately shutdown, does not
  do so.

  [Test Case]

    sudo systemctl mask systemd-logind.service
    sudo systemctl stop systemd-logind.service
    shutdown +1

  The expectation is that system goes to shutdown.

  It is buggy if the system remains up - i.e. command returns to shell
  with exit code 1.

  [Regression Potential]

   * It is a corner case to run against systemd-shim logind / or logind
  not otherwise available. The function still performs a clean-shutdown,
  and should not cause loss of work.

  [Other Info]
   
   * Original bug report, running against systemd-shim/systemd-service post 
trusty->xenial upgrade, pre-reboot.

  
  Used Landscape (Paid Canonical Subscription) to upgrade one of my machines.

  Landscape only shows "In Progress" for more than 8 hours now and asked
  for a reboot of the machine in a second alert.

  In the reboot attempt I get the message:
  =========================
  Failed to set wall message, ignoring: Method "SetWallMessage" with signature 
"sb" on interface "org.freedesktop.login1.Manager" doesn't exist
  Failed to call ScheduleShutdown in logind, proceeding with immediate 
shutdown: Method "ScheduleShutdown" with signature "st" on interface 
"org.freedesktop.login1.Manager" doesn't exist
  =========================

  Steps to reproduce:
  * Fully updated 14.04.5 machine
  * Open Landscape
  * Choose the machine
  * Choose Packages
  * This computer can be upgraded to a newer release
  * Apply
  * Wait 2 hours
  * Alert comes in a seperate Landscape message Machine is ready for reboot
  * Choose Info... Power
  * Deliver to selected computers as soon as possible
  * Error message

  I found this thread on reddit about this issue maybe the solution can be 
built into the upgrade script
  
https://www.reddit.com/r/linuxquestions/comments/4wy3go/trying_to_run_as_user_instance_but_the_system_has/

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