Hi, I had the same issue under Debian Wheezy with systemd 204-14~bpo70+1 As systemd is in constant development and Jessie is currently running version 215-5+b1 it maybe resolved in more recent versions than 204-14.
The solution provided under https://bugzilla.redhat.com/show_bug.cgi?id=626477 suggests to killall ssh sessions, when stopping sshd. I prefer to have at least one ssh session open to my server when restarting ssh, if something goes wrong. Therefore I added a service, to solve this under the current Debian Wheezy version I am running. /etc/systemd/system/ssh-user-sessions.service: [Unit] Description=Shutdown all ssh sessions before network After=network.target [Service] TimeoutStartSec=0 Type=oneshot RemainAfterExit=yes ExecStart=/bin/true ExecStop=/usr/bin/killall sshd When starting, this service does simply nothing (/bin/true). But due to the statement "After=network.target" it kills all ssh processes before shutting down the network. Works for me :-) Cheers Tom