Ran into this, too.

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https://bugs.launchpad.net/bugs/1476753

Title:
  When sshd exits because of a bad configuration, upstart claims the job
  is in "start/running" with no PID

Status in upstart package in Ubuntu:
  New

Bug description:
  Reproducible on 14.04 and 14.10

  In ssh's upstart config file, "expect stop" is used to signal upstart
  when sshd is ready to accept connections.  If the sshd config file is
  broken, sshd terminates before it sends SIGSTOP to itself and this
  seems to confuse upstart, such that it thinks the ssh job is still in
  start/running state (with no associated PID.)  In addition, I have
  another upstart job set to trigger on "start on stopped ssh
  RESULT=failed" which does _not_ trigger in this situation.

  If I comment out the "expect stop" stanza from ssh.conf then the sshd
  process properly ends up in "stop/waiting" and my other job triggers
  properly.

  Here is the DEBUG output from init when I start ssh with purposely
  broken sshd_config file

  Jul 19 16:47:43 patrick-vm kernel: [956961.180770] init: ssh goal changed 
from stop to start
  Jul 19 16:47:43 patrick-vm kernel: [956961.181056] init: ssh state changed 
from waiting to starting
  Jul 19 16:47:43 patrick-vm kernel: [956961.181333] init: event_new: Pending 
starting event
  Jul 19 16:47:43 patrick-vm kernel: [956961.181373] init: Handling starting 
event
  Jul 19 16:47:43 patrick-vm kernel: [956961.181535] init: event_finished: 
Finished starting event
  Jul 19 16:47:43 patrick-vm kernel: [956961.181548] init: ssh state changed 
from starting to security-spawning
  Jul 19 16:47:43 patrick-vm kernel: [956961.181814] init: ssh state changed 
from security-spawning to security
  Jul 19 16:47:43 patrick-vm kernel: [956961.182570] init: ssh state changed 
from security to pre-starting
  Jul 19 16:47:43 patrick-vm kernel: [956961.183593] init: ssh pre-start 
process (43674)
  Jul 19 16:47:43 patrick-vm kernel: [956961.183915] init: ssh state changed 
from pre-starting to pre-start
  Jul 19 16:47:43 patrick-vm kernel: [956961.187572] init: ssh pre-start 
process (43674) exited normally
  Jul 19 16:47:43 patrick-vm kernel: [956961.187664] init: ssh state changed 
from pre-start to spawning
  Jul 19 16:47:43 patrick-vm kernel: [956961.188352] init: ssh main process 
(43676)
  Jul 19 16:47:43 patrick-vm kernel: [956961.188512] init: ssh state changed 
from spawning to spawned
  Jul 19 16:47:43 patrick-vm kernel: [956961.193436] init: ssh main process 
(43676) terminated with status 255
  Jul 19 16:47:43 patrick-vm kernel: [956961.193467] init: ssh main process 
ended, respawning
  Jul 19 16:47:43 patrick-vm kernel: [956961.193531] init: ssh state changed 
from spawned to post-starting
  Jul 19 16:47:43 patrick-vm kernel: [956961.193896] init: ssh state changed 
from post-starting to post-start
  Jul 19 16:47:43 patrick-vm kernel: [956961.194419] init: ssh state changed 
from post-start to running
  Jul 19 16:47:43 patrick-vm kernel: [956961.194668] init: event_new: Pending 
started event
  Jul 19 16:47:43 patrick-vm kernel: [956961.194795] init: Handling started 
event
  Jul 19 16:47:43 patrick-vm kernel: [956961.194886] init: job_register: 
Registered instance /com/ubuntu/Upstart/jobs/startpar_2dbridge/ssh_2d_2dstarted
  Jul 19 16:47:43 patrick-vm kernel: [956961.194976] init: job_register: 
Registered instance /com/ubuntu/Upstart/jobs/startpar_2dbridge/ssh_2d_2dstarted
  Jul 19 16:47:43 patrick-vm kernel: [956961.195058] init: job_register: 
Registered instance /com/ubuntu/Upstart/jobs/startpar_2dbridge/ssh_2d_2dstarted
  Jul 19 16:47:43 patrick-vm kernel: [956961.195164] init: job_register: 
Registered instance /com/ubuntu/Upstart/jobs/startpar_2dbridge/ssh_2d_2dstarted
  Jul 19 16:47:43 patrick-vm kernel: [956961.195256] init: job_register: 
Registered instance /com/ubuntu/Upstart/jobs/startpar_2dbridge/ssh_2d_2dstarted
  Jul 19 16:47:43 patrick-vm kernel: [956961.195314] init: 
job_class_induct_job: New instance startpar-bridge (ssh--started)
  Jul 19 16:47:43 patrick-vm kernel: [956961.195333] init: startpar-bridge 
(ssh--started) goal changed from stop to start
  Jul 19 16:47:43 patrick-vm kernel: [956961.195634] init: startpar-bridge 
(ssh--started) state changed from waiting to starting
  Jul 19 16:47:43 patrick-vm kernel: [956961.195960] init: event_new: Pending 
starting event
  Jul 19 16:47:43 patrick-vm kernel: [956961.196154] init: Handling starting 
event
  Jul 19 16:47:43 patrick-vm kernel: [956961.196230] init: event_finished: 
Finished starting event
  Jul 19 16:47:43 patrick-vm kernel: [956961.196238] init: startpar-bridge 
(ssh--started) state changed from starting to security-spawning
  Jul 19 16:47:43 patrick-vm kernel: [956961.196459] init: startpar-bridge 
(ssh--started) state changed from security-spawning to security
  Jul 19 16:47:43 patrick-vm kernel: [956961.196667] init: startpar-bridge 
(ssh--started) state changed from security to pre-starting
  Jul 19 16:47:43 patrick-vm kernel: [956961.196864] init: startpar-bridge 
(ssh--started) state changed from pre-starting to pre-start
  Jul 19 16:47:43 patrick-vm kernel: [956961.197058] init: startpar-bridge 
(ssh--started) state changed from pre-start to spawning
  Jul 19 16:47:43 patrick-vm kernel: [956961.197616] init: startpar-bridge 
(ssh--started) main process (43677)
  Jul 19 16:47:43 patrick-vm kernel: [956961.197778] init: startpar-bridge 
(ssh--started) state changed from spawning to spawned
  Jul 19 16:47:43 patrick-vm kernel: [956961.199136] init: startpar-bridge 
(ssh--started) state changed from spawned to post-starting
  Jul 19 16:47:43 patrick-vm kernel: [956961.199455] init: startpar-bridge 
(ssh--started) state changed from post-starting to post-start
  Jul 19 16:47:43 patrick-vm kernel: [956961.199734] init: startpar-bridge 
(ssh--started) state changed from post-start to running
  Jul 19 16:47:43 patrick-vm kernel: [956961.199994] init: event_new: Pending 
started event
  Jul 19 16:47:43 patrick-vm kernel: [956961.200048] init: startpar-bridge 
(ssh--started) main process (43677) exited normally
  Jul 19 16:47:43 patrick-vm kernel: [956961.200165] init: startpar-bridge 
(ssh--started) goal changed from start to stop
  Jul 19 16:47:43 patrick-vm kernel: [956961.200421] init: startpar-bridge 
(ssh--started) state changed from running to stopping
  Jul 19 16:47:43 patrick-vm kernel: [956961.200683] init: event_new: Pending 
stopping event
  Jul 19 16:47:43 patrick-vm kernel: [956961.200706] init: Handling started 
event
  Jul 19 16:47:43 patrick-vm kernel: [956961.200903] init: event_finished: 
Finished started event
  Jul 19 16:47:43 patrick-vm kernel: [956961.201160] init: Handling stopping 
event
  Jul 19 16:47:43 patrick-vm kernel: [956961.201275] init: event_finished: 
Finished stopping event
  Jul 19 16:47:43 patrick-vm kernel: [956961.201285] init: startpar-bridge 
(ssh--started) state changed from stopping to killed
  Jul 19 16:47:43 patrick-vm kernel: [956961.201520] init: startpar-bridge 
(ssh--started) state changed from killed to post-stopping
  Jul 19 16:47:43 patrick-vm kernel: [956961.201756] init: startpar-bridge 
(ssh--started) state changed from post-stopping to post-stop
  Jul 19 16:47:43 patrick-vm kernel: [956961.202233] init: startpar-bridge 
(ssh--started) state changed from post-stop to waiting
  Jul 19 16:47:43 patrick-vm kernel: [956961.202498] init: event_new: Pending 
stopped event
  Jul 19 16:47:43 patrick-vm kernel: [956961.202528] init: job_change_state: 
Destroyed inactive instance startpar-bridge (ssh--started)
  Jul 19 16:47:43 patrick-vm kernel: [956961.203037] init: Handling stopped 
event
  Jul 19 16:47:43 patrick-vm kernel: [956961.203173] init: event_finished: 
Finished stopped event
  Jul 19 16:47:43 patrick-vm kernel: [956961.203446] init: event_finished: 
Finished started event

  
  My goal is to have an upstart job trigger in the event that sshd_config is 
broken and do something helpful , e.g. start another sshd on another port with 
a known good config so I can get back into the box to fix the problem.

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