If I hit any of the Restart options on the Home Assistant webpage it will not reload fully.
The HA Webpage will not come back up.
The same thing happens if I SSH in to Home Assistant and use the reboot command.
The image does reboot as it will drop the SSH terminal, after a while SSH comes back up and so does the Samba share.
The only way I can get it all to restart and bring the webpage back up is to reboot ResinOS over SSH.
Yes, that is a bug with homeassistant 0.44 and hass.io. We fix that on next homeassistant update 0.45.
Manual you can use the hass.io api over hass:
curl -X POST http://xy/api/hassio/homeassistant/restart
Brilliant, thank you 
exactly same issue as above but when I give above command over ssh shell it gives this
core-ssh:~# curl -X POST http://xy/api/hassio/homeassistant/restart
curl: (52) Empty reply from server
please help