An information processing system, computer readable storage medium, and method for documenting the execution of long running applications. A processor of the information processing system operates to continuously collect snapshots monitored from an executing application on a runtime system. The processor selects, based at least on user specified policies, collected snapshots that indicate a significant change in runtime behavior of the executing application on the runtime system. The processor annotates each of the selected snapshots with description of the significant change in runtime behavior of the executing application. The processor operates to store and update documentation of an execution history of the executing application from the annotated snapshots.