I am assuming that your using GUI tools rather than command-line. It seems that your running your ssh but its not starting automatically and then when it reboots it disables.
Open your terminal or Konsole whatever you prefer and then type in the commands:
$ sudo /etc/init.d/sshd start
$ sudo update-rc.d ssh defaults
(this should do the trick and do reboot and check if its working.)
Type following command to see what services or daemons are running on your server so that you can confirm yourself.
FYI, if you use RedHat or CentOS
and do check this link as well http://www.linuxquestions.org/questi...t-time-865692/