Same issue, since upgrade to 16.04 the system has hung during reboot.
The network isn't fully shutdown and responds to pings but sshd is
stopped, the system reboots successfully if swap is disabled. Attempted
to add reboot=force to grub, to no avail; only disabling swap fixed the
issue.

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https://bugs.launchpad.net/bugs/1582011

Title:
  Swap Failed, Indefinite hang on reboot/shutdown "Reached target
  Shutdown"

Status in systemd package in Ubuntu:
  Confirmed

Bug description:
  This bug has been affecting me since 15.04
  Prior to shutdown I activate debug-shell 'systemctl start debug-shell'
  I have followed bug #1464917 and installed Xenial-proposed with systemd 
229-4ubuntu5 package.  
  I have finally collected shutdown info using vt9.  
  Issues collecting info due to what I believe is a timeout where vt9 is not 
activated when ctl+alt+F9 is pressed.  I was able to collect info in vt9 to 
file "shutdown.text" I appended outputs to file "shutdown.text" the following 
commands in this order:
  systemctl list-jobs >>shutdown.text
  systemctl --failed >>shutdown.text
  uname -a >>shutdown.text
  systemd --version >>shutdown.text
  lsblk >>shutdown.text
  blkid >>shutdown.text
  journalctl -b >>shutdown.text
  systemctl -all >>shutdown.text
  journalctl -xe >>shutdown.text

  After gaining these data I was only able to finish the reboot with the 
alt+Sysrq and REISUB which forces a reboot even when I just want to shutdown
  Each output I separated upon next boot by hand with a line 
######################### for easier perusing.

  As a workaround for shutdown/reboot I turn swap off, 'sudo swapoff -a
  && systemctl poweroff' or 'sudo swapoff -a && reboot'  which
  occasionally fails if SWAP has more data than available RAM.  In that
  latter case I am left waiting for the hang and then using
  alt+Sysrq+REISUB to reboot then shutdown again immediately upon boot
  before SWAP has a chance to gain data, then I can use any form of
  halt, poweroff or menu to shutdown.

  I have been unable to get answers from AskUbuntu or the above listed
  bug #1464917 "Reached target Shutdown"  I am filing this bug per
  instructions requested in that bug.  Other systemd bugs I have
  researched #788303 Debian bug reports, #2930 Github and #3087 Github.

  Thanks for your time and efforts to help with this issue.

  ProblemType: Bug
  DistroRelease: Ubuntu 16.04
  Package: systemd 229-4ubuntu5
  ProcVersionSignature: Ubuntu 4.4.0-22.39-generic 4.4.8
  Uname: Linux 4.4.0-22-generic x86_64
  ApportVersion: 2.20.1-0ubuntu2
  Architecture: amd64
  Date: Sun May 15 12:08:34 2016
  ExecutablePath: /lib/systemd/systemd
  InstallationDate: Installed on 2015-06-29 (321 days ago)
  InstallationMedia: Ubuntu 15.04 "Vivid Vervet" - Release amd64 (20150422)
  MachineType: Sony Corporation VGN-FW250J
  ProcEnviron:
   LANG=en_US.UTF-8
   PATH=(custom, no user)
   SHELL=/bin/bash
   XDG_RUNTIME_DIR=<set>
  ProcKernelCmdLine: BOOT_IMAGE=/boot/vmlinuz-4.4.0-22-generic 
root=UUID=b010e611-6efb-49a9-bff0-59b9533d659b ro 
resume=UUID=8bcb4169-f5ab-4ab6-b644-23e528088d41 usbcore.autosuspend=-1
  SourcePackage: systemd
  SystemdDelta:
   [EXTENDED]   /lib/systemd/system/rc-local.service → 
/lib/systemd/system/rc-local.service.d/debian.conf
   [EXTENDED]   /etc/systemd/system/display-manager.service → 
/lib/systemd/system/display-manager.service.d/xdiagnose.conf
   [EXTENDED]   /lib/systemd/system/systemd-timesyncd.service → 
/lib/systemd/system/systemd-timesyncd.service.d/disable-with-time-daemon.conf
   
   3 overridden configuration files found.
  UpgradeStatus: Upgraded to xenial on 2016-04-26 (18 days ago)
  dmi.bios.date: 07/25/2008
  dmi.bios.vendor: American Megatrends Inc.
  dmi.bios.version: R1090Y0
  dmi.board.asset.tag: N/A
  dmi.board.name: VAIO
  dmi.board.vendor: Sony Corporation
  dmi.board.version: N/A
  dmi.chassis.asset.tag: N/A
  dmi.chassis.type: 10
  dmi.chassis.vendor: Sony Corporation
  dmi.chassis.version: N/A
  dmi.modalias: 
dmi:bvnAmericanMegatrendsInc.:bvrR1090Y0:bd07/25/2008:svnSonyCorporation:pnVGN-FW250J:pvrC6011MLK:rvnSonyCorporation:rnVAIO:rvrN/A:cvnSonyCorporation:ct10:cvrN/A:
  dmi.product.name: VGN-FW250J
  dmi.product.version: C6011MLK
  dmi.sys.vendor: Sony Corporation

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