A combined transaction execution monitoring, transaction classification and transaction execution performance anomaly detection system is disclosed. The system receives and analyzes transaction tracing data which may be provided by monitoring agents deployed to transaction executing entities like processes. In a first classification stage, parameters are extracted from received transaction tracing data, and the transaction tracing data is tagged with the extracted classification data. A subsequent measure extraction stage analyzes the classified transaction tracing data and creates corresponding measurements which are tagged with the transaction classifier. A following statistical analysis process maintains statistical data describing the long term statistical behavior of classified measures as a baseline, and also calculates corresponding statistical data describing the current statistical behavior of the classified measures. The statistical analysis process detects and notifies significant deviations between the statistical distribution of baseline and current measure data. A subsequent anomaly alerting and visualization stage processes those notifications.