Can you please get a journal from shutdown, as described in
/usr/share/doc/systemd/README.Debian ? Once it hangs, switch to the
debug shell, and do

  journalctl -ab > /root/journal.txt
  reboot -f

and then attach /root/journal.txt here. I suppose it's the "umount"
which times out on the network file system. There is not much that we
can do about it in systemd then (as it's umount itself which is
hanging), but let's first confirm what is the actual problem here.
Thanks!

** Changed in: systemd (Ubuntu)
       Status: New => Incomplete

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https://bugs.launchpad.net/bugs/1467943

Title:
  system shutdown hangs if btrfs on file image (mounted via cifs) is
  mounted

Status in systemd package in Ubuntu:
  Incomplete

Bug description:
  This happens if the network connection already failed before the
  shutdown has been requested. `systemd` should get into state where it
  refuses to proceed in shutdown.

  ProblemType: Bug
  DistroRelease: Ubuntu 15.04
  Package: systemd 219-7ubuntu6
  Uname: Linux 4.1.0-040100-generic x86_64
  ApportVersion: 2.17.2-0ubuntu1.1
  Architecture: amd64
  CurrentDesktop: Unity
  Date: Tue Jun 23 15:14:18 2015
  InstallationDate: Installed on 2015-06-08 (15 days ago)
  InstallationMedia: Ubuntu 14.04 LTS "Trusty Tahr" - Release amd64 (20140417)
  MachineType: LENOVO 20221
  ProcEnviron:
   TERM=xterm
   PATH=(custom, no user)
   XDG_RUNTIME_DIR=<set>
   LANG=de_DE.UTF-8
   SHELL=/bin/bash
  ProcKernelCmdLine: BOOT_IMAGE=/vmlinuz-4.1.0-040100-generic 
root=UUID=d665563a-2f33-4d06-bf9c-6838fe5ae3e9 ro 
rootflags=subvol=ubuntu-main-root
  SourcePackage: systemd
  UpgradeStatus: Upgraded to vivid on 2015-06-09 (14 days ago)
  dmi.bios.date: 07/12/2013
  dmi.bios.vendor: LENOVO
  dmi.bios.version: 71CN51WW(V1.21)
  dmi.board.asset.tag: No Asset Tag
  dmi.board.name: INVALID
  dmi.board.vendor: LENOVO
  dmi.board.version: 31900003WIN8 STD MLT
  dmi.chassis.asset.tag: No Asset Tag
  dmi.chassis.type: 10
  dmi.chassis.vendor: LENOVO
  dmi.chassis.version: Lenovo IdeaPad Z500 Touch
  dmi.modalias: 
dmi:bvnLENOVO:bvr71CN51WW(V1.21):bd07/12/2013:svnLENOVO:pn20221:pvrLenovoIdeaPadZ500Touch:rvnLENOVO:rnINVALID:rvr31900003WIN8STDMLT:cvnLENOVO:ct10:cvrLenovoIdeaPadZ500Touch:
  dmi.product.name: 20221
  dmi.product.version: Lenovo IdeaPad Z500 Touch
  dmi.sys.vendor: LENOVO

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