ifupdown is actually behaving correctly in this case.  It's likely that
cloud-initramfs-tools should be marking the interface "iface foo inet[6]
manual" in every case, since that's the indicator that seems to prevent
ifdown from downing the interface.

When I had it do that, what I then found was that we had gotten to
"reached shutdown target", and the system was then having timeouts in
systemd watchdogs.  Looking at it with systemd's debug shell, /media
/root-ro (the iscsi volume) has been unmounted, and /media/root-rw (the
overlayfs) is still mounted.

Interestingly, the last few things are:

[  OK  ] Unmounted /media/root-rw.
[  OK  ] Reached target Unmount All Filesystems.
[  OK  ] Stopped target Local File Systems (Pre).
         Stopped Monitoring of LVM2 mirrors, snapshots etc.  using dmeventd or 
progress polling...
[  OK  ] Stopped Remount Root and Kernel File Systems
[  OK  ] Stopped Create Static Device Nodes in /dev.
[  OK  ] Reached target Shutdown

5 seconds later is the "connection 1:0: ping timeout of 5 secs expired, ....
and / is still (or is that "again") mounted on overlayfs 
rw,relatime,lowerdir=/media/root-ro,upperdir=/media/root-rw//overlay,workdir=/media/root-rw//overlay-workdir

And then there is the collection of "INFO: task systemd:1 blocked for
more than 120 seconds." log entries on the console.

** Changed in: ifupdown (Ubuntu)
     Assignee: LaMont Jones (lamont) => (unassigned)

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https://bugs.launchpad.net/bugs/1629972

Title:
  networking stop incorrectly disconnects from (network) root filesystem

Status in MAAS:
  Triaged
Status in ifupdown package in Ubuntu:
  New
Status in ifupdown source package in Xenial:
  New

Bug description:
  With the switch to systemd, all support for iscsi root (and other)
  filesystems disappeared, since shutdown yanks the rug out from under
  us.

  Rather than just relying on /etc/iscsi/iscsi.initramfs (which d-i
  creates..), the DEV check should be expanded to include iscsi devices,
  and networking.service ExecStop should honor those checks.

  Related bugs:
    * bug 1229458: grub2 needed changes
    * bug 1621615: network not configured when ipv6 netbooted into cloud-init
    * bug 1621507: ipv6 network boot does not work

  [Impact]

  With the changes from the above, the iscsi root (at least in the ipv6
  case) gets disconneceted prior to clean shutdown (ifdown downs the
  interface), resulting in a failure to enlist, commission, or deploy
  cleanly under MAAS. (and a failure to cleanly unmount the root
  filesystem when it is over iscsi.)

  [Test Case]

  Given a MAAS 2.0 installation, and the packages in the other bugs,
  attempt to enlist, commission, or deploy a host with xenial.

  [Regression potential]

  This restores the pre-xenial behavior of not shutting down the
  interface if there are network drives at the time that neworking is
  stopped (making it a no-op.)  The additional change is to detect
  "/dev/disk/by-path/*-iscsi-*" as a network disk, replacing the check
  for the existence of /etc/iscsi/iscsi.initramfs, which was only
  created by debian-installer (and maas until recently).

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