The need for continuous monitoring (CM) is increasing. Collapses of multinational organizations have imposed strict regulatory and legislative requirements on organizations. This study develops an automated system and uses a large sample of accounts payable transaction data to simulate an implementation of continuous monitoring. The value of the system lies in its ability to translate business rules into configurable controls that evaluate transactions against expected results. The study demonstrates an application of continuous monitoring and the use of contextual meta‐data to perform rich audit analyses. Several anomalies reported by the CM system were not detected by the organization's internal auditors when they conducted their examination of the same data using conventional procedures. Such a system may potentially bring greater insights and transparency for continuous monitoring, assurance and organizational performance.