Configurable Computing Machines (CCMs) are computing machines based on reconfigurable circuit technology such as field programmable gate-arrays. Early researchers recognized CCMs as a new, flexible, and powerful class of computer. The earliest CCMs featured rudimentary but significant integrated design, debug, and deployment (runtime) environments. This paper reviews those environments and the contributions they made and considers the progress made over the past 20 years in providing support for the "3 D's" of configurable computing application development: design, debug, and deployment. It then introduces an integrated CAD framework for the creation of CCM CAD tools and describes a series of experiments in creating such a CAD tool suite -the JHDL system. The paper reviews lessons learned from that work and concludes by discussing the role integrated design, debug, and runtime environments will play in future CCM-based systems.