Same problem when running `reboot`, which I'd say is even more important
for automation. Port 2204 is forwarding to a qemu VM running Utopic,
port 2207 is running Vivid:

jderose@jgd-kudp1:~$ ssh root@localhost -p 2204 reboot
jderose@jgd-kudp1:~$ echo $?
0
jderose@jgd-kudp1:~$ ssh root@localhost -p 2207 reboot
Connection to localhost closed by remote host.
jderose@jgd-kudp1:~$ echo $?
255
jderose@jgd-kudp1:~$

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You received this bug notification because you are a member of Ubuntu
Touch seeded packages, which is subscribed to openssh in Ubuntu.
https://bugs.launchpad.net/bugs/1429938

Title:
  stopping ssh.service closes existing ssh connections

Status in openssh package in Ubuntu:
  Incomplete

Bug description:
  On Trusty and Utopic, when you run `apt-get remove openssh-server`
  over an SSH connection, your existing SSH connection remains open, so
  it's possible to run additional commands afterward.

  However, on Vivid now that the switch to systemd has been made,  `apt-
  get remove openssh-server` closes the existing SSH connection
  immediately, causing your SSH client to exit with a non-zero status. I
  have a hunch there's a lot of automation tooling out there that relies
  on the old behavior.

  For what it's worth, this change breaks the internal image mastering
  tools that System76 uses. Prior to exporting an image tarball, I spin
  up a golden VM with qemu, rysnc a script to it, and then execute this
  script over SSH.

  The important step is that I need to remove openssh-server prior to
  shutting down the VM, so these scripts always end with something like
  this:

  apt-get -y purge openssh-server ssh-import-id
  apt-get -y autoremove
  shutdown -h now

  As far as I can tell, this behavior change will likewise be a problem
  when running `do-release-upgrade` on a remote server over SSH. Or more
  generally, anytime you run "apt-get upgrade/dist-upgrade" via SSH, it
  seems this would be a problem whenever the openssh-server package
  happens to be updated.

To manage notifications about this bug go to:
https://bugs.launchpad.net/ubuntu/+source/openssh/+bug/1429938/+subscriptions

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