An application health monitoring system automatically resolves anomalies arising among clients of a messaging server. The messaging server clients (MSCs) include one or more applications and services included in the applications. The anomalies include MSC anomalies and process starter anomalies. When a messaging session is disconnected due to server restarts, the service may be automatically restarted a predetermined number of times to re-establish the connection. Similarly, if a process starter of a service fails to start up properly, the service can be automatically restarted a predetermined number of times before the anomaly is flagged for human review. The monitoring system also automatically implements rules whenever service configurations are changed in addition to validating web service ports and cloud provider queues.