Public bug reported:

System info:

$ lsb_release -rd

Description:    Ubuntu 16.04.6 LTS
Release:        16.04


$ apt-cache policy openssh-server

openssh-server:
  Installed: 1:7.2p2-4ubuntu2.9
  Candidate: 1:7.2p2-4ubuntu2.9
  Version table:
 *** 1:7.2p2-4ubuntu2.9 500
        500 https://mirror.one.com/ubuntu xenial-proposed/main amd64 Packages
        100 /var/lib/dpkg/status
     1:7.2p2-4ubuntu2.8 500
        500 https://mirror.one.com/ubuntu xenial-security/main amd64 Packages
        500 https://mirror.one.com/ubuntu xenial-updates/main amd64 Packages
        500 http://us.archive.ubuntu.com/ubuntu xenial-updates/main amd64 
Packages
     1:7.2p2-4 500
        500 https://mirror.one.com/ubuntu xenial/main amd64 Packages
        500 http://us.archive.ubuntu.com/ubuntu xenial/main amd64 Packages


 - what should happen?

After regular update ssh daemon should restart successfully.


 - what actually happens:

$ sudo apt-get -y update

[skip]

Fetched 2,473 B in 1s (1,702 B/s)
Reading package lists... Done


$ sudo apt-get -y dist-upgrade

Reading package lists... Done
Building dependency tree       
Reading state information... Done
Calculating upgrade... Done
The following packages were automatically installed and are no longer required:
  linux-headers-4.4.0-164 linux-headers-4.4.0-164-generic 
linux-image-4.4.0-164-generic linux-modules-4.4.0-164-generic 
linux-modules-extra-4.4.0-164-generic
Use 'sudo apt autoremove' to remove them.
0 upgraded, 0 newly installed, 0 to remove and 0 not upgraded.
1 not fully installed or removed.
After this operation, 0 B of additional disk space will be used.
Setting up openssh-server (1:7.2p2-4ubuntu2.9) ...
Job for ssh.service failed because a timeout was exceeded. See "systemctl 
status ssh.service" and "journalctl -xe" for details.
invoke-rc.d: initscript ssh, action "restart" failed.
● ssh.service - OpenBSD Secure Shell server
   Loaded: loaded (/lib/systemd/system/ssh.service; enabled; vendor preset: 
enabled)
   Active: activating (auto-restart) (Result: timeout) since Thu 2020-04-23 
17:21:42 MSK; 3ms ago
  Process: 9000 ExecStart=/usr/sbin/sshd -D $SSHD_OPTS (code=exited, 
status=0/SUCCESS)
  Process: 8996 ExecStartPre=/usr/sbin/sshd -t (code=exited, status=0/SUCCESS)
 Main PID: 9000 (code=exited, status=0/SUCCESS)

Apr 23 17:21:42 asrockZ97e systemd[1]: Failed to start OpenBSD Secure Shell 
server.
Apr 23 17:21:42 asrockZ97e systemd[1]: ssh.service: Unit entered failed state.
Apr 23 17:21:42 asrockZ97e systemd[1]: ssh.service: Failed with result 
'timeout'.
dpkg: error processing package openssh-server (--configure):
 subprocess installed post-installation script returned error exit status 1
Errors were encountered while processing:
 openssh-server
E: Sub-process /usr/bin/dpkg returned an error code (1)


However, if I check manually then everything seems fine:

$ ps aux | grep sshd | grep -v grep

root      9481  0.0  0.0  26212  3728 ?        Ss   17:23   0:00
/usr/sbin/sshd -D


$ sudo systemctl status sshd.service

● ssh.service - OpenBSD Secure Shell server
   Loaded: loaded (/lib/systemd/system/ssh.service; enabled; vendor preset: 
enabled)
   Active: activating (start) since Thu 2020-04-23 17:29:15 MSK; 1min 19s ago
  Process: 10454 ExecStartPre=/usr/sbin/sshd -t (code=exited, status=0/SUCCESS)
 Main PID: 10457 (sshd)
   CGroup: /system.slice/ssh.service
           ├─ 9759 sshd: ia [priv]
           ├─ 9771 sshd: ia@pts/18
           ├─ 9772 -zsh
           ├─10457 /usr/sbin/sshd -D
           ├─10750 sudo systemctl status sshd.service
           └─10760 systemctl status sshd.service

Apr 23 17:29:15 asrockZ97e systemd[1]: Starting OpenBSD Secure Shell server...
Apr 23 17:29:15 asrockZ97e sshd[10457]: Set /proc/self/oom_score_adj from 0 to 
-1000
Apr 23 17:29:15 asrockZ97e sshd[10457]: Server listening on 0.0.0.0 port 22.
Apr 23 17:29:15 asrockZ97e sshd[10457]: Server listening on :: port 22.
Apr 23 17:30:34 asrockZ97e sudo[10750]:       ia : TTY=pts/18 ; PWD=/home/ia ; 
USER=root ; COMMAND=/bin/systemctl status sshd.service
Apr 23 17:30:34 asrockZ97e sudo[10750]: pam_unix(sudo:session): session opened 
for user root by ia(uid=0)


$ ssh localhost

Last login: Thu Apr 23 17:01:34 2020


$


After some google fu, I found some recommendations about removing `-D' from 
`ExecStart' and replacing `Type=notify' by `Type=forking' in 
`/etc/systemd/system/sshd.service' but I'm not sure how accurate those hints 
are and what the real root cause behind such sudden and unexpected change in 
behavior.

P.S. I do realize that I use the package from `proposed' repo but I
don't think that it's the excuse for a such strange behavior after
upgrade.

** Affects: openssh (Ubuntu)
     Importance: Undecided
         Status: New


** Tags: openssh-server sshd status systemd timeout

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https://bugs.launchpad.net/bugs/1874455

Title:
  ssh daemon doesn't report successful start state to systemd after
  upgrade to 1:7.2p2-4ubuntu2.9

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