Upgrade Available -> Unhealthy State if I Wait a Few Days Before Upgrading

I’ve installed via the Supervisord method with the Docker containers running. This is terrific. However, often times if I miss a few days from when an upgrade is available then I need to restart the entire host to get to a healthy state before applying the upgrade. Is there something that is missing that would cause the system to report unhealthy after a period of time to gt an upgrade?