Most people still remember the introduction of the IBM PC in 1981 and the first Microsoft Windows operating system in 1985. These were the pioneering technologies that started a revolution in automotive test equipment in the service bay. What was once a purely mechanical garage environment where information was published annually in large paper manuals has evolved into a highly technical computing environment. Today vehicle networks link onboard vehicle control systems with diagnostic systems and updated service information is published daily over the Internet. A lot has changed over the last twenty years, and manufacturers of diagnostic test equipment are learning to deal with the constantly evolving computing platforms and host operating systems. This paper traces the history of automotive diagnostic equipment at Ford Motor Company and shares some of the hard lessons learned from the early systems. As technology forges ahead, there will continue to be challenges as well as opportunities. Those who have learned to evolve with technological advancements and embrace standards and legislation will not only lead the industry but also benefit from a smoother and more manageable future road map.