It definitely matters.

Posted Apr 4, 2008 15:45 UTC (Fri) by jospoortvliet (guest, #33164)
In reply to: It definitely matters. by beoba
Parent article: OpenSSH 5.0 released

Indeed. I would be much more careful to upgrade from 4.9 to 5.0 than from 5.0 to 5.1 or 5.1 to
5.1.1, yet it seems for OpenSSH you can simply never tell the size of the changes by version
number... Which is pretty annoying.