A site server agent monitors a site server for an event associated with an update process that spans multiple resources associated with multiple systems. The agent hands the monitoring off to a remote connected systems manager when a state associated with the event does not change to an expected value within a configured period of time or based on a configured condition. Connected systems manager continues to monitor the state and elevates the event to a level two incident after a second configured period of time or based on a second configured condition. When the state has still not changed after a third configured period of time or based on a third configured condition, a level one incident is generated in an incident management system associated with the site for support staff to immediately investigate the update process and resources of the systems.