This paper reports on the design and development of a digital compliance workbench. It examines a series of experimental developments over the course of 15 years to allow domain experts from the regulatory sector and from the design sector to create and deploy automated compliance checking. It explores the criteria that such a system must meet, examining each of Eastman’s 4-stage approach. Conclusion are drawn about the requirements for such a system, and the future development of the workbench and other solutions.