There have been some problems with 'sshd restart' etc. especially if config file is wrong (e.g. outdated sshd_config won't start with new sshd). There are a few bugzilla reports on this. If this something direly in need of getting more robust, you could consider applying: 20010806 - OpenBSD CVS Sync - stevesk.org 2001/07/26 17:18:22 [sshd.8 sshd.c] add -t option to test configuration file and keys; pekkas ok markus@ Running 'sshd -t' before 'restart' and 'condrestart' in init.d/sshd script, and requiring it will pass before doing restart might reduce the cases where your connection is killed if new sshd is not restarted due to some error. (it's pretty late for this, and I'm not sure if this is viewed as something very important, but here it is anyway...)
Doing so would only postpone the startup failure to next-boot, and also potentially break from the restart-on-upgrade behavior most packages exchibit. As I have no strong feeling either way about this, I'm inclined to mark this bug "deferred" and just go with what the upstream init script will do once the patch works its way into a release. If you believe that this can't wait, please reopen this bug.