A rising main pipeline assessment system and method. An analysis system obtains data recorded on the pipeline and generates a steady state hydraulic model for the pipeline which defines expected performance zones under normal operating conditions and zone boundaries delineating normal and abnormal operating conditions. Model data is recorded in a data repository of the processing hub. A monitoring system includes a pipeline-connectable pressure transducer configured to obtain measurements during operation of the pipeline and generate, for each of a plurality of predetermined time periods, a data record including minimum, maximum and mean measurements. The data record is communicated to a processing hub which is configured to classify each received data record measurement according to its measurements and the performance zones of the model. The processing hub monitors the classified data records for each performance zone and generates an alarm upon identifying a predetermined pattern of classified data records.