Yes, the HoloPorts will be designed and released to run unattended (including self upgrades, etc) once the initial security and connection configurations are performed.

In case of an outright failure of hardware or software, there is a color coded indicator light on the outside of the case, which can alert you to an issue. You can then login to an application that will give you more details about the state of the machine + actions you can perform to correct a situation if needed.