My first suspicion is that the interface that the iscsi device is on
lives in /etc/network/interfaces (or interfaces.d/*) somewhere and thus
is being shut down by networking.service. Ordinarily this network
interface is being set up in initramfs by open-iscsi and should not
otherwise be configured/touched by the OS (i. e. not by ifupdown,
NetworkManager, or networkd).

 - Which network interface is the iscsi device on, and how did you configure 
this?
 - Please attach /etc/network/interfaces*

It would also be useful to attach a complete shutdown log. Do a reboot
and attach /var/log/syslog, that should have sufficient data for the
network interface shutdowns (it won't cover the open-iscsi error though
as that happens too late, but we have that part in the screenshot).

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

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https://bugs.launchpad.net/bugs/1569925

Title:
  Shutdown hang on 16.04 with iscsi targets

Status in systemd package in Ubuntu:
  Incomplete

Bug description:
  I have 4 servers running the latest 16.04 updates from the development
  branch (as of right now).

  Each server is connected to NetApp storage using iscsi software
  initiator.  There are a total of 56 volumes spread across two NetApp
  arrays.  Each volume has 4 paths available to it which are being
  managed by device mapper.

  While logged into the iscsi sessions all I have to do is reboot the
  server and I get a hang.

  I see a message that says:

    "Reached target Shutdown"

  followed by

    "systemd-shutdown[1]: Failed to finalize DM devices, ignoring"

  and then I see 8 lines that say:

    "connection1:0: ping timeout of 5 secs expired, recv timeout 5, last rx 
4311815***, last ping 43118164**, now 4311817***"
    "connection2:0: ping timeout of 5 secs expired, recv timeout 5, last rx 
4311815***, last ping 43118164**, now 4311817***"
    "connection3:0: ping timeout of 5 secs expired, recv timeout 5, last rx 
4311815***, last ping 43118164**, now 4311817***"
    "connection4:0: ping timeout of 5 secs expired, recv timeout 5, last rx 
4311815***, last ping 43118164**, now 4311817***"
    "connection5:0: ping timeout of 5 secs expired, recv timeout 5, last rx 
4311815***, last ping 43118164**, now 4311817***"
    "connection6:0: ping timeout of 5 secs expired, recv timeout 5, last rx 
4311815***, last ping 43118164**, now 4311817***"
    "connection7:0: ping timeout of 5 secs expired, recv timeout 5, last rx 
4311815***, last ping 43118164**, now 4311817***"
    "connection8:0: ping timeout of 5 secs expired, recv timeout 5, last rx 
4311815***, last ping 43118164**, now 4311817***"
    NOTE: the actual values of the *'s differ for each line above.

  This seems like a bug somewhere but I am unaware of any additional
  logging that I could turn on to pinpoint the problem.

  Note I also have similar setups that are not doing iscsi and they
  don't have this problem.

  Here is a screenshot of what I see on the shell when I try to reboot:

  https://www.dropbox.com/s/93mv7cj8asspcpa/ShutdownCapture.JPG?dl=0

  This is being tracked in NetApp bug tracker CQ number 860251.

  If I log out of all iscsi sessions before rebooting then I do not
  experience the hang:

  iscsiadm -m node -U all

  We are wondering if this could be some kind of shutdown ordering
  problem.  Like the network devices have already disappeared and then
  iscsi tries to perform some operation (hence the ping timeouts).

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