SSH not starting on boot

Had a system running perfectly for a while, but had to move to a new SD-card. Of course I backupped the full configuration etc.

After installing the latest (0.71.0) image on the SD-card for Raspberry Pi 2B+ it booted. To be able to set things up I installed the SSH addon without problems, inserted my public SSH key and started the ssh server I was able to log into it.

After setting things up (setting my config back, installing addons) I restarted the Raspberry Pi ($ reboot now). After rebooting Hass showed up, but was not accessible through SSH anymore. Stupid as I am I disabled the HASSIO menu, and since I had no way to get it back without SSH I had to reflash the image and start over again.

Knowing better, this time I setup SSH again and kept the HASSIO submenu active for the time being. After the full setup I wanted to reboot the Pi again ($ reboot now), but again… no SSH. This time even Hass itself did not show up, but the Pihole addon did!

Note that I had the SSH plugin “start on boot”. I checked it multiple times on both tries. Even tested it again but SSH does not seem to work with start on boot anymore…

So now what? For some reason HASS does not start after a reboot, although the config is perfectly fine. SSH does not start on boot so even if I accidentily break the configuration, I have no way to recover it.

I know Home Assistant is still in heavy development (0.X versioning), but these glitches are really annoying. Every time I break my config I have to reflash the whole system and start over setting things up. There is NO-WAY to recover the system if there is no SSH or webGUI it seems. Anyone else facing these issues with the SSH addon?

Hi - my OpenSSH is also not starting on boot even though toggled to do so.
Have you been able to solve your issue?