Normally Datto would push the OS updates for the appliance automatically on the back end and this would not be noticeable. However, when you see the message “A software upgrade is available for this device” on the homepage of your Datto, that means that this important OS update needs to be run with your consent, since it would require a reboot of the appliance. So you should proceed with it when you see it to make sure that your Datto appliance is fully up to date.